(a) Interpretation: Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated. Concept Introduction: Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β -hydroxy aldol or β -hydroxy ketone . This product further gives dehydration or condensation product by elimination small molecule such as water.

Question

Want to see more full solutions like this?

Answer 1

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 22, Problem 22.22P

Interpretation Introduction

(a)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized using aldol condensation in good yield. The starting materials are p−methoxybenzaldehyde and pentan−3−one.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 1

Figure 1

In the above preparation of the compound, the enolate is generated on the α− carbon of the pentan−3−one which is favorable to be generated on ketone rather than aldehyde. The enolate is then attack on the electrophilic carbon of the p−methoxybenzaldehyde to produce β−hydroxyketone which is finally dehydrated to give the condensed product. Therefore, the given compound is synthesized using aldol condensation in good yield. The structures of the starting materials which are used to produce the given compound are shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 2

Figure 2

Conclusion

The given compound can be synthesized by aldol condensation of p−methoxybenzaldehyde and pentan−3−one.

Interpretation Introduction

(b)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized using aldol condensation in good yield. The starting materials are benzaldehyde and hexan−3−one.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 3

Figure 3

In the preparation of the above compound, the enolate will be generated on the α− carbon of hexan−3−one which is favorable to be generated on ketone rather than aldehyde. The enolate will then attack the electrophilic carbon of the benzaldehyde to produce the β−hydroxyketone which is finally dehydrated to give the condensed product.

The structures of the starting materials which are used to produce the given compound are shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 4

Figure 4

Conclusion

The given compound can be synthesized by aldol condensation of benzaldehyde and hexan−3−one.

Interpretation Introduction

(c)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized using aldol condensation but not in a good in good yield. The starting material is 7−oxoctanal.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 5

Figure 5

In the preparation of the above compound, intramolecular aldol condensation takes place. To form this compound enolate must be generated by aldehyde and it has to attack the carbonyl carbon of ketone which is not favorable condition. Favorable condition is that enolate should be generated on ketone which attacks the electrophilic carbon of the aldehyde. This is because the carbon of aldehyde is more acidic than the carbon of ketone. The structure of the starting material which is used to produce the given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 6

Figure 6

Therefore, the given compound cannot be synthesized by aldol condensation in a good yield.

Conclusion

This compound cannot be synthesized in a good yield by the aldol condensation.

Interpretation Introduction

(d)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized by aldol condensation in good yield. The starting material is 6−oxoheptanal.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 7

Figure 7

The given compound, is prepared by the intramolecular aldol condensation of 6−oxoheptanal to produce the β−hydroxyketone which is finally dehydrated to give the condensed product. This compound is prepared in a good yield because of the presence of the three acidic carbon atoms which results in the formation of carbanion at three different places. The structure of the starting material which is used to produce the given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 8

Figure 8

Conclusion

The given compound can be synthesized by intramolecular aldol condensation of 6−oxoheptanal in a good yield.

Interpretation Introduction

(e)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized from aldol condensation in a good yield. The starting materials are: 1,3−diphenylpropan−2−one and benzil.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 9

Figure 9

In the preparation of the given compound, the enolate will be generated on the α-carbon of the ketone group of 1,3−diphenylpropan−2−one which is the only possibility of generation of enolate in the 1,3−diphenylpropan−2−one. The enolate will then attack the electrophilic carbon of the ketone group of the benzil to produce β−hydroxyketone which is finally dehydrated to give the condensed product. The structures of the starting materials are shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 10

Figure 10

Conclusion

The given compound can be synthesized by aldol condensation of 1,3−diphenylpropan−2−one and benzyl in a good yield.

Interpretation Introduction

(f)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized by aldol condensation in a good yield. The starting materials are 2 moles of benzaldehyde and acetone.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 11

Figure 11

In the preparation of the compound, the enolate is generated on the α-carbon of the ketonic group of acetone which is favorable to be generated on ketone rather than aldehyde. The enolate will then attack the electrophilic carbon of the aldehyde group of the benzaldehyde to produce β−hydroxyketone is finally dehydrated to give the condensed product. The structures of the starting materials for the preparation of the given compound are shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 12

Figure 12

Conclusion

The given compound can be synthesized by aldol condensation of benzaldehyde and acetone.

Interpretation Introduction

(g)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized by aldol condensation. The starting materials are trimethylacetone and acetaldehyde.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 13

Figure 13

In the preparation of the given compound, the enolate will be generated on the α-carbon of the ketonic group of trimethylacetone which is favorable to be generated on ketone rather than aldehyde. The enolate will then attack the electrophilic carbon of the aldehyde group of the acetaldehyde to produce β−hydroxyketone which is finally dehydrated to give the condensed product. The structures of the starting materials, acetaldehyde and trimethylacetone are shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 14

Figure 14

Conclusion

The given compound can be synthesized by aldol condensation by trimethylacetone and acetaldehyde in a good yield.

Interpretation Introduction

(h)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized by aldol condensation in a good yield. The starting material is cyclodecan−1,6−dione.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 15

Figure 15

The enolate will be generated on the α-carbon of the ketonic group of cyclodecan−1,6−dione which is favorable to be generated on ketone rather than aldehyde. The enolate will then attack the electrophilic carbon of the aldehyde group of the cyclodecan−1,6−dione to produce β−hydroxyketone which is finally dehydrated to give the condensed product. The structure of the starting material is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 16

Figure 16

Conclusion

The given compound can be synthesized by aldol condensation of cyclodecan−1,6−dione in a good yield.

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Students have asked these similar questions

(a) State and illustrate the following :(i) Wolff-Kishner reduction (ii) Aldol condensation(b) An organic compound (A) which has characteristic odour, on treatment with NaOH forms two compounds (B) and (C). Compound (B) has the molecular formula C7H8O which on oxidation with CrO3 gives back compound (A). Compound (C) is the sodium salt of the acid. Compound (C) when heated with soda lime yields an aromatic hydrocarbon (D). Deduce the structures of (A), (B), (C) and (D). Write chemical equations for all reactions taking place.

Provide the structure of the intramolecular aldol condensation dehydration products that result when diketone (A), below is heated and sodium hydroxide (A= heptane-2,6-dione)

The following questions pertain to the esters shown and behavior under conditions of the Claisen condensation.(a) Two of these esters are converted to β-keto esters in good yield on treatment with sodium ethoxide and subsequent acidification of the reaction mixture. Which two are these? Write the structure of the Claisen condensation product of each one. (b) One ester is capable of being converted to a β-keto ester on treatment with sodium ethoxide, but the amount of β-keto ester that can be isolated after acidification of the reaction mixture is quite small. Which ester is this? (c) One ester is incapable of reaction under conditions of the Claisen condensation. Which one? Why?

Answer 2

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 22, Problem 22.22P

Interpretation Introduction

(a)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized using aldol condensation in good yield. The starting materials are p−methoxybenzaldehyde and pentan−3−one.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 1

Figure 1

In the above preparation of the compound, the enolate is generated on the α− carbon of the pentan−3−one which is favorable to be generated on ketone rather than aldehyde. The enolate is then attack on the electrophilic carbon of the p−methoxybenzaldehyde to produce β−hydroxyketone which is finally dehydrated to give the condensed product. Therefore, the given compound is synthesized using aldol condensation in good yield. The structures of the starting materials which are used to produce the given compound are shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 2

Figure 2

Conclusion

The given compound can be synthesized by aldol condensation of p−methoxybenzaldehyde and pentan−3−one.

Interpretation Introduction

(b)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized using aldol condensation in good yield. The starting materials are benzaldehyde and hexan−3−one.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 3

Figure 3

In the preparation of the above compound, the enolate will be generated on the α− carbon of hexan−3−one which is favorable to be generated on ketone rather than aldehyde. The enolate will then attack the electrophilic carbon of the benzaldehyde to produce the β−hydroxyketone which is finally dehydrated to give the condensed product.

The structures of the starting materials which are used to produce the given compound are shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 4

Figure 4

Conclusion

The given compound can be synthesized by aldol condensation of benzaldehyde and hexan−3−one.

Interpretation Introduction

(c)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized using aldol condensation but not in a good in good yield. The starting material is 7−oxoctanal.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 5

Figure 5

In the preparation of the above compound, intramolecular aldol condensation takes place. To form this compound enolate must be generated by aldehyde and it has to attack the carbonyl carbon of ketone which is not favorable condition. Favorable condition is that enolate should be generated on ketone which attacks the electrophilic carbon of the aldehyde. This is because the carbon of aldehyde is more acidic than the carbon of ketone. The structure of the starting material which is used to produce the given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 6

Figure 6

Therefore, the given compound cannot be synthesized by aldol condensation in a good yield.

Conclusion

This compound cannot be synthesized in a good yield by the aldol condensation.

Interpretation Introduction

(d)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized by aldol condensation in good yield. The starting material is 6−oxoheptanal.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 7

Figure 7

The given compound, is prepared by the intramolecular aldol condensation of 6−oxoheptanal to produce the β−hydroxyketone which is finally dehydrated to give the condensed product. This compound is prepared in a good yield because of the presence of the three acidic carbon atoms which results in the formation of carbanion at three different places. The structure of the starting material which is used to produce the given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 8

Figure 8

Conclusion

The given compound can be synthesized by intramolecular aldol condensation of 6−oxoheptanal in a good yield.

Interpretation Introduction

(e)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized from aldol condensation in a good yield. The starting materials are: 1,3−diphenylpropan−2−one and benzil.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 9

Figure 9

In the preparation of the given compound, the enolate will be generated on the α-carbon of the ketone group of 1,3−diphenylpropan−2−one which is the only possibility of generation of enolate in the 1,3−diphenylpropan−2−one. The enolate will then attack the electrophilic carbon of the ketone group of the benzil to produce β−hydroxyketone which is finally dehydrated to give the condensed product. The structures of the starting materials are shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 10

Figure 10

Conclusion

The given compound can be synthesized by aldol condensation of 1,3−diphenylpropan−2−one and benzyl in a good yield.

Interpretation Introduction

(f)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized by aldol condensation in a good yield. The starting materials are 2 moles of benzaldehyde and acetone.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 11

Figure 11

In the preparation of the compound, the enolate is generated on the α-carbon of the ketonic group of acetone which is favorable to be generated on ketone rather than aldehyde. The enolate will then attack the electrophilic carbon of the aldehyde group of the benzaldehyde to produce β−hydroxyketone is finally dehydrated to give the condensed product. The structures of the starting materials for the preparation of the given compound are shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 12

Figure 12

Conclusion

The given compound can be synthesized by aldol condensation of benzaldehyde and acetone.

Interpretation Introduction

(g)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized by aldol condensation. The starting materials are trimethylacetone and acetaldehyde.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 13

Figure 13

In the preparation of the given compound, the enolate will be generated on the α-carbon of the ketonic group of trimethylacetone which is favorable to be generated on ketone rather than aldehyde. The enolate will then attack the electrophilic carbon of the aldehyde group of the acetaldehyde to produce β−hydroxyketone which is finally dehydrated to give the condensed product. The structures of the starting materials, acetaldehyde and trimethylacetone are shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 14

Figure 14

Conclusion

The given compound can be synthesized by aldol condensation by trimethylacetone and acetaldehyde in a good yield.

Interpretation Introduction

(h)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized by aldol condensation in a good yield. The starting material is cyclodecan−1,6−dione.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 15

Figure 15

The enolate will be generated on the α-carbon of the ketonic group of cyclodecan−1,6−dione which is favorable to be generated on ketone rather than aldehyde. The enolate will then attack the electrophilic carbon of the aldehyde group of the cyclodecan−1,6−dione to produce β−hydroxyketone which is finally dehydrated to give the condensed product. The structure of the starting material is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 16

Figure 16

Conclusion

The given compound can be synthesized by aldol condensation of cyclodecan−1,6−dione in a good yield.

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Answer 3

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 22, Problem 22.22P

Interpretation Introduction

(a)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized using aldol condensation in good yield. The starting materials are p−methoxybenzaldehyde and pentan−3−one.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 1

Figure 1

In the above preparation of the compound, the enolate is generated on the α− carbon of the pentan−3−one which is favorable to be generated on ketone rather than aldehyde. The enolate is then attack on the electrophilic carbon of the p−methoxybenzaldehyde to produce β−hydroxyketone which is finally dehydrated to give the condensed product. Therefore, the given compound is synthesized using aldol condensation in good yield. The structures of the starting materials which are used to produce the given compound are shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 2

Figure 2

Conclusion

The given compound can be synthesized by aldol condensation of p−methoxybenzaldehyde and pentan−3−one.

Interpretation Introduction

(b)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized using aldol condensation in good yield. The starting materials are benzaldehyde and hexan−3−one.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 3

Figure 3

In the preparation of the above compound, the enolate will be generated on the α− carbon of hexan−3−one which is favorable to be generated on ketone rather than aldehyde. The enolate will then attack the electrophilic carbon of the benzaldehyde to produce the β−hydroxyketone which is finally dehydrated to give the condensed product.

The structures of the starting materials which are used to produce the given compound are shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 4

Figure 4

Conclusion

The given compound can be synthesized by aldol condensation of benzaldehyde and hexan−3−one.

Interpretation Introduction

(c)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized using aldol condensation but not in a good in good yield. The starting material is 7−oxoctanal.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 5

Figure 5

In the preparation of the above compound, intramolecular aldol condensation takes place. To form this compound enolate must be generated by aldehyde and it has to attack the carbonyl carbon of ketone which is not favorable condition. Favorable condition is that enolate should be generated on ketone which attacks the electrophilic carbon of the aldehyde. This is because the carbon of aldehyde is more acidic than the carbon of ketone. The structure of the starting material which is used to produce the given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 6

Figure 6

Therefore, the given compound cannot be synthesized by aldol condensation in a good yield.

Conclusion

This compound cannot be synthesized in a good yield by the aldol condensation.

Interpretation Introduction

(d)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized by aldol condensation in good yield. The starting material is 6−oxoheptanal.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 7

Figure 7

The given compound, is prepared by the intramolecular aldol condensation of 6−oxoheptanal to produce the β−hydroxyketone which is finally dehydrated to give the condensed product. This compound is prepared in a good yield because of the presence of the three acidic carbon atoms which results in the formation of carbanion at three different places. The structure of the starting material which is used to produce the given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 8

Figure 8

Conclusion

The given compound can be synthesized by intramolecular aldol condensation of 6−oxoheptanal in a good yield.

Interpretation Introduction

(e)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized from aldol condensation in a good yield. The starting materials are: 1,3−diphenylpropan−2−one and benzil.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 9

Figure 9

In the preparation of the given compound, the enolate will be generated on the α-carbon of the ketone group of 1,3−diphenylpropan−2−one which is the only possibility of generation of enolate in the 1,3−diphenylpropan−2−one. The enolate will then attack the electrophilic carbon of the ketone group of the benzil to produce β−hydroxyketone which is finally dehydrated to give the condensed product. The structures of the starting materials are shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 10

Figure 10

Conclusion

The given compound can be synthesized by aldol condensation of 1,3−diphenylpropan−2−one and benzyl in a good yield.

Interpretation Introduction

(f)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized by aldol condensation in a good yield. The starting materials are 2 moles of benzaldehyde and acetone.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 11

Figure 11

In the preparation of the compound, the enolate is generated on the α-carbon of the ketonic group of acetone which is favorable to be generated on ketone rather than aldehyde. The enolate will then attack the electrophilic carbon of the aldehyde group of the benzaldehyde to produce β−hydroxyketone is finally dehydrated to give the condensed product. The structures of the starting materials for the preparation of the given compound are shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 12

Figure 12

Conclusion

The given compound can be synthesized by aldol condensation of benzaldehyde and acetone.

Interpretation Introduction

(g)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized by aldol condensation. The starting materials are trimethylacetone and acetaldehyde.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 13

Figure 13

In the preparation of the given compound, the enolate will be generated on the α-carbon of the ketonic group of trimethylacetone which is favorable to be generated on ketone rather than aldehyde. The enolate will then attack the electrophilic carbon of the aldehyde group of the acetaldehyde to produce β−hydroxyketone which is finally dehydrated to give the condensed product. The structures of the starting materials, acetaldehyde and trimethylacetone are shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 14

Figure 14

Conclusion

The given compound can be synthesized by aldol condensation by trimethylacetone and acetaldehyde in a good yield.

Interpretation Introduction

(h)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized by aldol condensation in a good yield. The starting material is cyclodecan−1,6−dione.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 15

Figure 15

The enolate will be generated on the α-carbon of the ketonic group of cyclodecan−1,6−dione which is favorable to be generated on ketone rather than aldehyde. The enolate will then attack the electrophilic carbon of the aldehyde group of the cyclodecan−1,6−dione to produce β−hydroxyketone which is finally dehydrated to give the condensed product. The structure of the starting material is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 16

Figure 16

Conclusion

The given compound can be synthesized by aldol condensation of cyclodecan−1,6−dione in a good yield.

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Answer 4

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 22, Problem 22.22P

Interpretation Introduction

(a)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized using aldol condensation in good yield. The starting materials are p−methoxybenzaldehyde and pentan−3−one.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 1

Figure 1

In the above preparation of the compound, the enolate is generated on the α− carbon of the pentan−3−one which is favorable to be generated on ketone rather than aldehyde. The enolate is then attack on the electrophilic carbon of the p−methoxybenzaldehyde to produce β−hydroxyketone which is finally dehydrated to give the condensed product. Therefore, the given compound is synthesized using aldol condensation in good yield. The structures of the starting materials which are used to produce the given compound are shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 2

Figure 2

Conclusion

The given compound can be synthesized by aldol condensation of p−methoxybenzaldehyde and pentan−3−one.

Interpretation Introduction

(b)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized using aldol condensation in good yield. The starting materials are benzaldehyde and hexan−3−one.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 3

Figure 3

In the preparation of the above compound, the enolate will be generated on the α− carbon of hexan−3−one which is favorable to be generated on ketone rather than aldehyde. The enolate will then attack the electrophilic carbon of the benzaldehyde to produce the β−hydroxyketone which is finally dehydrated to give the condensed product.

The structures of the starting materials which are used to produce the given compound are shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 4

Figure 4

Conclusion

The given compound can be synthesized by aldol condensation of benzaldehyde and hexan−3−one.

Interpretation Introduction

(c)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized using aldol condensation but not in a good in good yield. The starting material is 7−oxoctanal.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 5

Figure 5

In the preparation of the above compound, intramolecular aldol condensation takes place. To form this compound enolate must be generated by aldehyde and it has to attack the carbonyl carbon of ketone which is not favorable condition. Favorable condition is that enolate should be generated on ketone which attacks the electrophilic carbon of the aldehyde. This is because the carbon of aldehyde is more acidic than the carbon of ketone. The structure of the starting material which is used to produce the given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 6

Figure 6

Therefore, the given compound cannot be synthesized by aldol condensation in a good yield.

Conclusion

This compound cannot be synthesized in a good yield by the aldol condensation.

Interpretation Introduction

(d)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized by aldol condensation in good yield. The starting material is 6−oxoheptanal.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 7

Figure 7

The given compound, is prepared by the intramolecular aldol condensation of 6−oxoheptanal to produce the β−hydroxyketone which is finally dehydrated to give the condensed product. This compound is prepared in a good yield because of the presence of the three acidic carbon atoms which results in the formation of carbanion at three different places. The structure of the starting material which is used to produce the given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 8

Figure 8

Conclusion

The given compound can be synthesized by intramolecular aldol condensation of 6−oxoheptanal in a good yield.

Interpretation Introduction

(e)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized from aldol condensation in a good yield. The starting materials are: 1,3−diphenylpropan−2−one and benzil.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 9

Figure 9

In the preparation of the given compound, the enolate will be generated on the α-carbon of the ketone group of 1,3−diphenylpropan−2−one which is the only possibility of generation of enolate in the 1,3−diphenylpropan−2−one. The enolate will then attack the electrophilic carbon of the ketone group of the benzil to produce β−hydroxyketone which is finally dehydrated to give the condensed product. The structures of the starting materials are shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 10

Figure 10

Conclusion

The given compound can be synthesized by aldol condensation of 1,3−diphenylpropan−2−one and benzyl in a good yield.

Interpretation Introduction

(f)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized by aldol condensation in a good yield. The starting materials are 2 moles of benzaldehyde and acetone.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 11

Figure 11

In the preparation of the compound, the enolate is generated on the α-carbon of the ketonic group of acetone which is favorable to be generated on ketone rather than aldehyde. The enolate will then attack the electrophilic carbon of the aldehyde group of the benzaldehyde to produce β−hydroxyketone is finally dehydrated to give the condensed product. The structures of the starting materials for the preparation of the given compound are shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 12

Figure 12

Conclusion

The given compound can be synthesized by aldol condensation of benzaldehyde and acetone.

Interpretation Introduction

(g)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized by aldol condensation. The starting materials are trimethylacetone and acetaldehyde.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 13

Figure 13

In the preparation of the given compound, the enolate will be generated on the α-carbon of the ketonic group of trimethylacetone which is favorable to be generated on ketone rather than aldehyde. The enolate will then attack the electrophilic carbon of the aldehyde group of the acetaldehyde to produce β−hydroxyketone which is finally dehydrated to give the condensed product. The structures of the starting materials, acetaldehyde and trimethylacetone are shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 14

Figure 14

Conclusion

The given compound can be synthesized by aldol condensation by trimethylacetone and acetaldehyde in a good yield.

Interpretation Introduction

(h)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized by aldol condensation in a good yield. The starting material is cyclodecan−1,6−dione.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 15

Figure 15

The enolate will be generated on the α-carbon of the ketonic group of cyclodecan−1,6−dione which is favorable to be generated on ketone rather than aldehyde. The enolate will then attack the electrophilic carbon of the aldehyde group of the cyclodecan−1,6−dione to produce β−hydroxyketone which is finally dehydrated to give the condensed product. The structure of the starting material is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 16

Figure 16

Conclusion

The given compound can be synthesized by aldol condensation of cyclodecan−1,6−dione in a good yield.

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Answer 5

Chapter 22, Problem 22.22P

Interpretation Introduction

(a)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized using aldol condensation in good yield. The starting materials are p−methoxybenzaldehyde and pentan−3−one.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 1

Figure 1

In the above preparation of the compound, the enolate is generated on the α− carbon of the pentan−3−one which is favorable to be generated on ketone rather than aldehyde. The enolate is then attack on the electrophilic carbon of the p−methoxybenzaldehyde to produce β−hydroxyketone which is finally dehydrated to give the condensed product. Therefore, the given compound is synthesized using aldol condensation in good yield. The structures of the starting materials which are used to produce the given compound are shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 2

Figure 2

Conclusion

The given compound can be synthesized by aldol condensation of p−methoxybenzaldehyde and pentan−3−one.

Interpretation Introduction

(b)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized using aldol condensation in good yield. The starting materials are benzaldehyde and hexan−3−one.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 3

Figure 3

In the preparation of the above compound, the enolate will be generated on the α− carbon of hexan−3−one which is favorable to be generated on ketone rather than aldehyde. The enolate will then attack the electrophilic carbon of the benzaldehyde to produce the β−hydroxyketone which is finally dehydrated to give the condensed product.

The structures of the starting materials which are used to produce the given compound are shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 4

Figure 4

Conclusion

The given compound can be synthesized by aldol condensation of benzaldehyde and hexan−3−one.

Interpretation Introduction

(c)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized using aldol condensation but not in a good in good yield. The starting material is 7−oxoctanal.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 5

Figure 5

In the preparation of the above compound, intramolecular aldol condensation takes place. To form this compound enolate must be generated by aldehyde and it has to attack the carbonyl carbon of ketone which is not favorable condition. Favorable condition is that enolate should be generated on ketone which attacks the electrophilic carbon of the aldehyde. This is because the carbon of aldehyde is more acidic than the carbon of ketone. The structure of the starting material which is used to produce the given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 6

Figure 6

Therefore, the given compound cannot be synthesized by aldol condensation in a good yield.

Conclusion

This compound cannot be synthesized in a good yield by the aldol condensation.

Interpretation Introduction

(d)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized by aldol condensation in good yield. The starting material is 6−oxoheptanal.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 7

Figure 7

The given compound, is prepared by the intramolecular aldol condensation of 6−oxoheptanal to produce the β−hydroxyketone which is finally dehydrated to give the condensed product. This compound is prepared in a good yield because of the presence of the three acidic carbon atoms which results in the formation of carbanion at three different places. The structure of the starting material which is used to produce the given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 8

Figure 8

Conclusion

The given compound can be synthesized by intramolecular aldol condensation of 6−oxoheptanal in a good yield.

Interpretation Introduction

(e)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized from aldol condensation in a good yield. The starting materials are: 1,3−diphenylpropan−2−one and benzil.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 9

Figure 9

In the preparation of the given compound, the enolate will be generated on the α-carbon of the ketone group of 1,3−diphenylpropan−2−one which is the only possibility of generation of enolate in the 1,3−diphenylpropan−2−one. The enolate will then attack the electrophilic carbon of the ketone group of the benzil to produce β−hydroxyketone which is finally dehydrated to give the condensed product. The structures of the starting materials are shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 10

Figure 10

Conclusion

The given compound can be synthesized by aldol condensation of 1,3−diphenylpropan−2−one and benzyl in a good yield.

Interpretation Introduction

(f)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized by aldol condensation in a good yield. The starting materials are 2 moles of benzaldehyde and acetone.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 11

Figure 11

In the preparation of the compound, the enolate is generated on the α-carbon of the ketonic group of acetone which is favorable to be generated on ketone rather than aldehyde. The enolate will then attack the electrophilic carbon of the aldehyde group of the benzaldehyde to produce β−hydroxyketone is finally dehydrated to give the condensed product. The structures of the starting materials for the preparation of the given compound are shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 12

Figure 12

Conclusion

The given compound can be synthesized by aldol condensation of benzaldehyde and acetone.

Interpretation Introduction

(g)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized by aldol condensation. The starting materials are trimethylacetone and acetaldehyde.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 13

Figure 13

In the preparation of the given compound, the enolate will be generated on the α-carbon of the ketonic group of trimethylacetone which is favorable to be generated on ketone rather than aldehyde. The enolate will then attack the electrophilic carbon of the aldehyde group of the acetaldehyde to produce β−hydroxyketone which is finally dehydrated to give the condensed product. The structures of the starting materials, acetaldehyde and trimethylacetone are shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 14

Figure 14

Conclusion

The given compound can be synthesized by aldol condensation by trimethylacetone and acetaldehyde in a good yield.

Interpretation Introduction

(h)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized by aldol condensation in a good yield. The starting material is cyclodecan−1,6−dione.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 15

Figure 15

The enolate will be generated on the α-carbon of the ketonic group of cyclodecan−1,6−dione which is favorable to be generated on ketone rather than aldehyde. The enolate will then attack the electrophilic carbon of the aldehyde group of the cyclodecan−1,6−dione to produce β−hydroxyketone which is finally dehydrated to give the condensed product. The structure of the starting material is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 16

Figure 16

Conclusion

The given compound can be synthesized by aldol condensation of cyclodecan−1,6−dione in a good yield.

Answer 6

Chapter 22, Problem 22.22P

Interpretation Introduction

(a)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized using aldol condensation in good yield. The starting materials are p−methoxybenzaldehyde and pentan−3−one.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 1

Figure 1

In the above preparation of the compound, the enolate is generated on the α− carbon of the pentan−3−one which is favorable to be generated on ketone rather than aldehyde. The enolate is then attack on the electrophilic carbon of the p−methoxybenzaldehyde to produce β−hydroxyketone which is finally dehydrated to give the condensed product. Therefore, the given compound is synthesized using aldol condensation in good yield. The structures of the starting materials which are used to produce the given compound are shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 2

Figure 2

Conclusion

The given compound can be synthesized by aldol condensation of p−methoxybenzaldehyde and pentan−3−one.

Answer 7

Chapter 22, Problem 22.22P

Interpretation Introduction

(a)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Answer 8

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized using aldol condensation in good yield. The starting materials are p−methoxybenzaldehyde and pentan−3−one.

Answer 9

Expert Solution

Answer 10

Expert Solution

Answer 11

Expert Solution

Answer 12

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 1

Figure 1

In the above preparation of the compound, the enolate is generated on the α− carbon of the pentan−3−one which is favorable to be generated on ketone rather than aldehyde. The enolate is then attack on the electrophilic carbon of the p−methoxybenzaldehyde to produce β−hydroxyketone which is finally dehydrated to give the condensed product. Therefore, the given compound is synthesized using aldol condensation in good yield. The structures of the starting materials which are used to produce the given compound are shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 2

Figure 2

Answer 13

Conclusion

The given compound can be synthesized by aldol condensation of p−methoxybenzaldehyde and pentan−3−one.

Answer 14

Interpretation Introduction

(b)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized using aldol condensation in good yield. The starting materials are benzaldehyde and hexan−3−one.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 3

Figure 3

In the preparation of the above compound, the enolate will be generated on the α− carbon of hexan−3−one which is favorable to be generated on ketone rather than aldehyde. The enolate will then attack the electrophilic carbon of the benzaldehyde to produce the β−hydroxyketone which is finally dehydrated to give the condensed product.

The structures of the starting materials which are used to produce the given compound are shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 4

Figure 4

Conclusion

The given compound can be synthesized by aldol condensation of benzaldehyde and hexan−3−one.

Answer 15

Interpretation Introduction

(b)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Answer 16

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized using aldol condensation in good yield. The starting materials are benzaldehyde and hexan−3−one.

Answer 17

Expert Solution

Answer 18

Expert Solution

Answer 19

Expert Solution

Answer 20

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 3

Figure 3

In the preparation of the above compound, the enolate will be generated on the α− carbon of hexan−3−one which is favorable to be generated on ketone rather than aldehyde. The enolate will then attack the electrophilic carbon of the benzaldehyde to produce the β−hydroxyketone which is finally dehydrated to give the condensed product.

The structures of the starting materials which are used to produce the given compound are shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 4

Figure 4

Answer 21

Conclusion

The given compound can be synthesized by aldol condensation of benzaldehyde and hexan−3−one.

Answer 22

Interpretation Introduction

(c)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized using aldol condensation but not in a good in good yield. The starting material is 7−oxoctanal.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 5

Figure 5

In the preparation of the above compound, intramolecular aldol condensation takes place. To form this compound enolate must be generated by aldehyde and it has to attack the carbonyl carbon of ketone which is not favorable condition. Favorable condition is that enolate should be generated on ketone which attacks the electrophilic carbon of the aldehyde. This is because the carbon of aldehyde is more acidic than the carbon of ketone. The structure of the starting material which is used to produce the given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 6

Figure 6

Therefore, the given compound cannot be synthesized by aldol condensation in a good yield.

Conclusion

This compound cannot be synthesized in a good yield by the aldol condensation.

Answer 23

Interpretation Introduction

(c)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Answer 24

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized using aldol condensation but not in a good in good yield. The starting material is 7−oxoctanal.

Answer 25

Expert Solution

Answer 26

Expert Solution

Answer 27

Expert Solution

Answer 28

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 5

Figure 5

In the preparation of the above compound, intramolecular aldol condensation takes place. To form this compound enolate must be generated by aldehyde and it has to attack the carbonyl carbon of ketone which is not favorable condition. Favorable condition is that enolate should be generated on ketone which attacks the electrophilic carbon of the aldehyde. This is because the carbon of aldehyde is more acidic than the carbon of ketone. The structure of the starting material which is used to produce the given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 6

Figure 6

Therefore, the given compound cannot be synthesized by aldol condensation in a good yield.

Answer 29

Conclusion

This compound cannot be synthesized in a good yield by the aldol condensation.

Answer 30

Interpretation Introduction

(d)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized by aldol condensation in good yield. The starting material is 6−oxoheptanal.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 7

Figure 7

The given compound, is prepared by the intramolecular aldol condensation of 6−oxoheptanal to produce the β−hydroxyketone which is finally dehydrated to give the condensed product. This compound is prepared in a good yield because of the presence of the three acidic carbon atoms which results in the formation of carbanion at three different places. The structure of the starting material which is used to produce the given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 8

Figure 8

Conclusion

The given compound can be synthesized by intramolecular aldol condensation of 6−oxoheptanal in a good yield.

Answer 31

Interpretation Introduction

(d)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Answer 32

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized by aldol condensation in good yield. The starting material is 6−oxoheptanal.

Answer 33

Expert Solution

Answer 34

Expert Solution

Answer 35

Expert Solution

Answer 36

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 7

Figure 7

The given compound, is prepared by the intramolecular aldol condensation of 6−oxoheptanal to produce the β−hydroxyketone which is finally dehydrated to give the condensed product. This compound is prepared in a good yield because of the presence of the three acidic carbon atoms which results in the formation of carbanion at three different places. The structure of the starting material which is used to produce the given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 8

Figure 8

Answer 37

Conclusion

The given compound can be synthesized by intramolecular aldol condensation of 6−oxoheptanal in a good yield.

Answer 38

Interpretation Introduction

(e)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized from aldol condensation in a good yield. The starting materials are: 1,3−diphenylpropan−2−one and benzil.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 9

Figure 9

In the preparation of the given compound, the enolate will be generated on the α-carbon of the ketone group of 1,3−diphenylpropan−2−one which is the only possibility of generation of enolate in the 1,3−diphenylpropan−2−one. The enolate will then attack the electrophilic carbon of the ketone group of the benzil to produce β−hydroxyketone which is finally dehydrated to give the condensed product. The structures of the starting materials are shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 10

Figure 10

Conclusion

The given compound can be synthesized by aldol condensation of 1,3−diphenylpropan−2−one and benzyl in a good yield.

Answer 39

Interpretation Introduction

(e)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Answer 40

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized from aldol condensation in a good yield. The starting materials are: 1,3−diphenylpropan−2−one and benzil.

Answer 41

Expert Solution

Answer 42

Expert Solution

Answer 43

Expert Solution

Answer 44

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 9

Figure 9

In the preparation of the given compound, the enolate will be generated on the α-carbon of the ketone group of 1,3−diphenylpropan−2−one which is the only possibility of generation of enolate in the 1,3−diphenylpropan−2−one. The enolate will then attack the electrophilic carbon of the ketone group of the benzil to produce β−hydroxyketone which is finally dehydrated to give the condensed product. The structures of the starting materials are shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 10

Figure 10

Answer 45

Conclusion

The given compound can be synthesized by aldol condensation of 1,3−diphenylpropan−2−one and benzyl in a good yield.

Answer 46

Interpretation Introduction

(f)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized by aldol condensation in a good yield. The starting materials are 2 moles of benzaldehyde and acetone.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 11

Figure 11

In the preparation of the compound, the enolate is generated on the α-carbon of the ketonic group of acetone which is favorable to be generated on ketone rather than aldehyde. The enolate will then attack the electrophilic carbon of the aldehyde group of the benzaldehyde to produce β−hydroxyketone is finally dehydrated to give the condensed product. The structures of the starting materials for the preparation of the given compound are shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 12

Figure 12

Conclusion

The given compound can be synthesized by aldol condensation of benzaldehyde and acetone.

Answer 47

Interpretation Introduction

(f)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Answer 48

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized by aldol condensation in a good yield. The starting materials are 2 moles of benzaldehyde and acetone.

Answer 49

Expert Solution

Answer 50

Expert Solution

Answer 51

Expert Solution

Answer 52

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 11

Figure 11

In the preparation of the compound, the enolate is generated on the α-carbon of the ketonic group of acetone which is favorable to be generated on ketone rather than aldehyde. The enolate will then attack the electrophilic carbon of the aldehyde group of the benzaldehyde to produce β−hydroxyketone is finally dehydrated to give the condensed product. The structures of the starting materials for the preparation of the given compound are shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 12

Figure 12

Answer 53

Conclusion

The given compound can be synthesized by aldol condensation of benzaldehyde and acetone.

Answer 54

Interpretation Introduction

(g)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized by aldol condensation. The starting materials are trimethylacetone and acetaldehyde.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 13

Figure 13

In the preparation of the given compound, the enolate will be generated on the α-carbon of the ketonic group of trimethylacetone which is favorable to be generated on ketone rather than aldehyde. The enolate will then attack the electrophilic carbon of the aldehyde group of the acetaldehyde to produce β−hydroxyketone which is finally dehydrated to give the condensed product. The structures of the starting materials, acetaldehyde and trimethylacetone are shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 14

Figure 14

Conclusion

The given compound can be synthesized by aldol condensation by trimethylacetone and acetaldehyde in a good yield.

Answer 55

Interpretation Introduction

(g)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Answer 56

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized by aldol condensation. The starting materials are trimethylacetone and acetaldehyde.

Answer 57

Expert Solution

Answer 58

Expert Solution

Answer 59

Expert Solution

Answer 60

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 13

Figure 13

In the preparation of the given compound, the enolate will be generated on the α-carbon of the ketonic group of trimethylacetone which is favorable to be generated on ketone rather than aldehyde. The enolate will then attack the electrophilic carbon of the aldehyde group of the acetaldehyde to produce β−hydroxyketone which is finally dehydrated to give the condensed product. The structures of the starting materials, acetaldehyde and trimethylacetone are shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 14

Figure 14

Answer 61

Conclusion

The given compound can be synthesized by aldol condensation by trimethylacetone and acetaldehyde in a good yield.

Answer 62

Interpretation Introduction

(h)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized by aldol condensation in a good yield. The starting material is cyclodecan−1,6−dione.

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 15

Figure 15

The enolate will be generated on the α-carbon of the ketonic group of cyclodecan−1,6−dione which is favorable to be generated on ketone rather than aldehyde. The enolate will then attack the electrophilic carbon of the aldehyde group of the cyclodecan−1,6−dione to produce β−hydroxyketone which is finally dehydrated to give the condensed product. The structure of the starting material is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 16

Figure 16

Conclusion

The given compound can be synthesized by aldol condensation of cyclodecan−1,6−dione in a good yield.

Answer 63

Interpretation Introduction

(h)

Interpretation:

Whether the given compound is synthesized in good yield or not by an aldol condensation with its starting materials is to be stated. The reason as to why the required aldol condensation would not succeed for compound that is not synthesized in good yield is to be stated.

Concept Introduction:

Aldol condensation is the nucleophilic addition reaction of the carbonyl compounds. An enolate ion generated from one of the carbonyl compound attack the electrophilic carbon of the other carbonyl compound to produce β-hydroxy aldol or β-hydroxy ketone. This product further gives dehydration or condensation product by elimination small molecule such as water.

Answer 64

Expert Solution

Answer to Problem 22.22P

The given compound can be synthesized by aldol condensation in a good yield. The starting material is cyclodecan−1,6−dione.

Answer 65

Expert Solution

Answer 66

Expert Solution

Answer 67

Expert Solution

Answer 68

Explanation of Solution

The given compound is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 15

Figure 15

The enolate will be generated on the α-carbon of the ketonic group of cyclodecan−1,6−dione which is favorable to be generated on ketone rather than aldehyde. The enolate will then attack the electrophilic carbon of the aldehyde group of the cyclodecan−1,6−dione to produce β−hydroxyketone which is finally dehydrated to give the condensed product. The structure of the starting material is shown below.

ORGANIC CHEMISTRY SAPLING ACCESS + ETEX, Chapter 22, Problem 22.22P , additional homework tip 16

Figure 16

Answer 69

Conclusion

The given compound can be synthesized by aldol condensation of cyclodecan−1,6−dione in a good yield.

Answer 70

Ch. 22 - Prob. 22.1P Ch. 22 - Prob. 22.2P Ch. 22 - Prob. 22.3P Ch. 22 - Prob. 22.4P Ch. 22 - Prob. 22.5P Ch. 22 - Prob. 22.6P Ch. 22 - Prob. 22.7P Ch. 22 - Prob. 22.8P Ch. 22 - Prob. 22.9P Ch. 22 - Prob. 22.10P

Concept explainers

Videos

Answer to Problem 22.22P

Explanation of Solution

Answer to Problem 22.22P

Explanation of Solution

Answer to Problem 22.22P

Explanation of Solution

Answer to Problem 22.22P

Explanation of Solution

Answer to Problem 22.22P

Explanation of Solution

Answer to Problem 22.22P

Explanation of Solution

Answer to Problem 22.22P

Explanation of Solution

Answer to Problem 22.22P

Explanation of Solution

Want to see more full solutions like this?

Chapter 22 Solutions