a) Interpretation: The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction is to be shown. Concept introduction: Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon within the same molecule or of the second molecule to give an aldol. The aldol dehydrates on heating to yield α, β-unsaturated aldehyde or ketone. To show: The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction.

Question

Provide a chemical reaction on how the following compounds can be synthesized via aldol condensation. note that the starting reactants should be benzaldehyde and a ketone

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 23.SE, Problem 49AP

Interpretation Introduction

a)

Interpretation:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction is to be shown.

Concept introduction:

Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon within the same molecule or of the second molecule to give an aldol. The aldol dehydrates on heating to yield α, β-unsaturated aldehyde or ketone.

To show:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction.

Interpretation Introduction

b)

Interpretation:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction is to be shown.

Concept introduction:

Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon within the same molecule or of the second molecule to give an aldol. The aldol dehydrates on heating to yield α, β-unsaturated aldehyde or ketone.

To show:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction.

Interpretation Introduction

c)

Interpretation:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction is to be shown.

Concept introduction:

Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon within the same molecule or of the second molecule to give an aldol. The aldol dehydrates on heating to yield α, β-unsaturated aldehyde or ketone.

To show:

The structure of the aldehyde that should be used as a starting material to synthesize the compound given in an aldol reaction.

Interpretation Introduction

d)

Interpretation:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction is to be shown.

Concept introduction:

Mixed aldol condensation leads to a single product if i)one of the carbonyl partners contains no α hydrogen atoms but contains an unhindered carbonyl group and ii) if one of the carbonyl partners are much more acidic than the other and thus forms an enolate anion in preference to other.

To show:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction.

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Provide a chemical reaction on how the following compounds can be synthesized via aldol condensation. note that the starting reactants should be benzaldehyde and a ketone

Show how to prepare a,b-unsaturated ketone by an aldol reaction followed by dehydration of the aldol product.

2 H3C H3C H C→XT OH H3C The aldol reaction is a carbonyl condensation reaction between two carbonyl partners and involves a combination of nucleophilic addition and a-substitution steps. One partner is converted into an enolate ion nucleophile and adds to the electrophilic carbonyl group of the second partner. In the classic aldol reaction, the carbonyl partners are aldehydes or ketones, although aldehydes are more reactive. The product is a ß-hydroxy carbonyl compound. base :0: OH H H Under reaction conditions slightly more vigorous than those employed for the aldol reaction, the ß-hydroxyl group is eliminated in an E1cB dehydration to give an a,ß-unsaturated carbonyl compound. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instruct ns H3C heat OH H3C :0: H + H₂O H

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 23.SE, Problem 49AP

Interpretation Introduction

a)

Interpretation:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction is to be shown.

Concept introduction:

Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon within the same molecule or of the second molecule to give an aldol. The aldol dehydrates on heating to yield α, β-unsaturated aldehyde or ketone.

To show:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction.

Interpretation Introduction

b)

Interpretation:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction is to be shown.

Concept introduction:

Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon within the same molecule or of the second molecule to give an aldol. The aldol dehydrates on heating to yield α, β-unsaturated aldehyde or ketone.

To show:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction.

Interpretation Introduction

c)

Interpretation:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction is to be shown.

Concept introduction:

Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon within the same molecule or of the second molecule to give an aldol. The aldol dehydrates on heating to yield α, β-unsaturated aldehyde or ketone.

To show:

The structure of the aldehyde that should be used as a starting material to synthesize the compound given in an aldol reaction.

Interpretation Introduction

d)

Interpretation:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction is to be shown.

Concept introduction:

Mixed aldol condensation leads to a single product if i)one of the carbonyl partners contains no α hydrogen atoms but contains an unhindered carbonyl group and ii) if one of the carbonyl partners are much more acidic than the other and thus forms an enolate anion in preference to other.

To show:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction.

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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 23.SE, Problem 49AP

Interpretation Introduction

a)

Interpretation:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction is to be shown.

Concept introduction:

Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon within the same molecule or of the second molecule to give an aldol. The aldol dehydrates on heating to yield α, β-unsaturated aldehyde or ketone.

To show:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction.

Interpretation Introduction

b)

Interpretation:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction is to be shown.

Concept introduction:

Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon within the same molecule or of the second molecule to give an aldol. The aldol dehydrates on heating to yield α, β-unsaturated aldehyde or ketone.

To show:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction.

Interpretation Introduction

c)

Interpretation:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction is to be shown.

Concept introduction:

Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon within the same molecule or of the second molecule to give an aldol. The aldol dehydrates on heating to yield α, β-unsaturated aldehyde or ketone.

To show:

The structure of the aldehyde that should be used as a starting material to synthesize the compound given in an aldol reaction.

Interpretation Introduction

d)

Interpretation:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction is to be shown.

Concept introduction:

Mixed aldol condensation leads to a single product if i)one of the carbonyl partners contains no α hydrogen atoms but contains an unhindered carbonyl group and ii) if one of the carbonyl partners are much more acidic than the other and thus forms an enolate anion in preference to other.

To show:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction.

Expert Solution & Answer

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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 23.SE, Problem 49AP

Interpretation Introduction

a)

Interpretation:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction is to be shown.

Concept introduction:

Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon within the same molecule or of the second molecule to give an aldol. The aldol dehydrates on heating to yield α, β-unsaturated aldehyde or ketone.

To show:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction.

Interpretation Introduction

b)

Interpretation:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction is to be shown.

Concept introduction:

Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon within the same molecule or of the second molecule to give an aldol. The aldol dehydrates on heating to yield α, β-unsaturated aldehyde or ketone.

To show:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction.

Interpretation Introduction

c)

Interpretation:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction is to be shown.

Concept introduction:

Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon within the same molecule or of the second molecule to give an aldol. The aldol dehydrates on heating to yield α, β-unsaturated aldehyde or ketone.

To show:

The structure of the aldehyde that should be used as a starting material to synthesize the compound given in an aldol reaction.

Interpretation Introduction

d)

Interpretation:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction is to be shown.

Concept introduction:

Mixed aldol condensation leads to a single product if i)one of the carbonyl partners contains no α hydrogen atoms but contains an unhindered carbonyl group and ii) if one of the carbonyl partners are much more acidic than the other and thus forms an enolate anion in preference to other.

To show:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction.

Expert Solution & Answer

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Answer 5

Chapter 23.SE, Problem 49AP

Interpretation Introduction

a)

Interpretation:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction is to be shown.

Concept introduction:

Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon within the same molecule or of the second molecule to give an aldol. The aldol dehydrates on heating to yield α, β-unsaturated aldehyde or ketone.

To show:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction.

Interpretation Introduction

b)

Interpretation:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction is to be shown.

Concept introduction:

Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon within the same molecule or of the second molecule to give an aldol. The aldol dehydrates on heating to yield α, β-unsaturated aldehyde or ketone.

To show:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction.

Interpretation Introduction

c)

Interpretation:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction is to be shown.

Concept introduction:

Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon within the same molecule or of the second molecule to give an aldol. The aldol dehydrates on heating to yield α, β-unsaturated aldehyde or ketone.

To show:

The structure of the aldehyde that should be used as a starting material to synthesize the compound given in an aldol reaction.

Interpretation Introduction

d)

Interpretation:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction is to be shown.

Concept introduction:

Mixed aldol condensation leads to a single product if i)one of the carbonyl partners contains no α hydrogen atoms but contains an unhindered carbonyl group and ii) if one of the carbonyl partners are much more acidic than the other and thus forms an enolate anion in preference to other.

To show:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction.

Answer 6

Chapter 23.SE, Problem 49AP

Interpretation Introduction

a)

Interpretation:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction is to be shown.

Concept introduction:

Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon within the same molecule or of the second molecule to give an aldol. The aldol dehydrates on heating to yield α, β-unsaturated aldehyde or ketone.

To show:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction.

Answer 7

Chapter 23.SE, Problem 49AP

Interpretation Introduction

a)

Interpretation:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction is to be shown.

Concept introduction:

Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon within the same molecule or of the second molecule to give an aldol. The aldol dehydrates on heating to yield α, β-unsaturated aldehyde or ketone.

To show:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction.

Answer 8

Interpretation Introduction

b)

Interpretation:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction is to be shown.

Concept introduction:

Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon within the same molecule or of the second molecule to give an aldol. The aldol dehydrates on heating to yield α, β-unsaturated aldehyde or ketone.

To show:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction.

Answer 9

Interpretation Introduction

b)

Interpretation:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction is to be shown.

Concept introduction:

Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon within the same molecule or of the second molecule to give an aldol. The aldol dehydrates on heating to yield α, β-unsaturated aldehyde or ketone.

To show:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction.

Answer 10

Interpretation Introduction

c)

Interpretation:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction is to be shown.

Concept introduction:

Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon within the same molecule or of the second molecule to give an aldol. The aldol dehydrates on heating to yield α, β-unsaturated aldehyde or ketone.

To show:

The structure of the aldehyde that should be used as a starting material to synthesize the compound given in an aldol reaction.

Answer 11

Interpretation Introduction

c)

Interpretation:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction is to be shown.

Concept introduction:

Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon within the same molecule or of the second molecule to give an aldol. The aldol dehydrates on heating to yield α, β-unsaturated aldehyde or ketone.

To show:

The structure of the aldehyde that should be used as a starting material to synthesize the compound given in an aldol reaction.

Answer 12

Interpretation Introduction

d)

Interpretation:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction is to be shown.

Concept introduction:

Mixed aldol condensation leads to a single product if i)one of the carbonyl partners contains no α hydrogen atoms but contains an unhindered carbonyl group and ii) if one of the carbonyl partners are much more acidic than the other and thus forms an enolate anion in preference to other.

To show:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction.

Answer 13

Interpretation Introduction

d)

Interpretation:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction is to be shown.

Concept introduction:

Mixed aldol condensation leads to a single product if i)one of the carbonyl partners contains no α hydrogen atoms but contains an unhindered carbonyl group and ii) if one of the carbonyl partners are much more acidic than the other and thus forms an enolate anion in preference to other.

To show:

The structure of the aldehydes or ketones that should be used as a starting material to synthesize the compound given in an aldol reaction.

Answer 14

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Ch. 23.1 - Prob. 1P Ch. 23.1 - Prob. 2P Ch. 23.3 - Prob. 3P Ch. 23.3 - Prob. 4P Ch. 23.4 - Prob. 5P Ch. 23.4 - 1-Butanol is prepared commercially by a route that...Ch. 23.4 - Prob. 7P Ch. 23.5 - Prob. 8P Ch. 23.6 - Prob. 9P Ch. 23.6 - What product would you Expect to obtain from base...

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