(a) Interpretation: The compounds needed to carry out Step [1] are to be stated. Concept introduction: In crossed claisen condensation reaction, the base abstracts the acidic proton from α − carbon atom of an ester to form enolate. This enolate reacts with carbonyl group of other ester that leads to the formation of a β-keto ester . The crossed Claisen condensation always takes place between the two different carbonyl compounds.

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Answer 1

Question

Chapter 24, Problem 24.68P

Interpretation Introduction

(a)

Interpretation:

The compounds needed to carry out Step [1] are to be stated.

Concept introduction:

In crossed claisen condensation reaction, the base abstracts the acidic proton from α− carbon atom of an ester to form enolate. This enolate reacts with carbonyl group of other ester that leads to the formation of a β-keto ester. The crossed Claisen condensation always takes place between the two different carbonyl compounds.

Interpretation Introduction

(b)

Interpretation:

The compounds needed to carry out Step [1] are to be stated.

Concept introduction:

In crossed claisen condensation reaction, the base abstracts the acidic proton from α− carbon atom of an ester to form enolate. This enolate reacts with carbonyl group of other ester that leads to the formation of a β-keto ester. The crossed Claisen condensation always takes place between the two different carbonyl compounds.

Interpretation Introduction

(c)

Interpretation:

The detailed mechanism for step [3] is to be drawn.

Concept introduction:

When only one carbonyl component has an alpha hydrogen atom, then a cross aldol reaction will occur. There will be formation of only one product. The yield of single cross aldol condensation reaction is enhanced if the electrophilic carbonyl compound is relatively unhindered.

Interpretation Introduction

(d)

Interpretation:

The detailed mechanism for step [4] is to be drawn. The reason as to why the product formed is unusual is to be stated.

Concept introduction:

When only one carbonyl component has an alpha hydrogen atom, then a cross aldol reaction will occur. There will be formation of only one product. The yield of single cross aldol condensation reaction is enhanced if the electrophilic carbonyl compound is relatively unhindered.

Interpretation Introduction

(e)

Interpretation:

The reason behind the unnecessary addition and removal of formyl group is to be predicted.

Concept introduction:

When only one carbonyl component has an alpha hydrogen atom, then a cross aldol reaction will occur. There will be formation of only one product. The yield of single cross aldol condensation reaction is enhanced if the electrophilic carbonyl compound is relatively unhindered.

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The use of curved arrows is a powerful tool that illustrates even complex reactions. a.Add curved arrows to show how carbocation A is converted to carbocation B. Label each new σ bond formed. Similar reactions have been used in elegant syntheses of steroids. b.Draw the product by following the curved arrows. This reaction is an example of a [3,3] sigmatropic rearrangement, as we will learn in Chapter 25.

Chemistry Find the most efficient synthetic route for the followinf transformations.

Consider the following alkyl halides: - may react with NaI to give JKL? - an alkyl iodide that will give SN1 and E1 product? - has the highest boiling point? - most likely to give retention and inversion products in SN1 reaction? - most likely to give rearrangement product in SN1?

Answer 2

Question

Chapter 24, Problem 24.68P

Interpretation Introduction

(a)

Interpretation:

The compounds needed to carry out Step [1] are to be stated.

Concept introduction:

In crossed claisen condensation reaction, the base abstracts the acidic proton from α− carbon atom of an ester to form enolate. This enolate reacts with carbonyl group of other ester that leads to the formation of a β-keto ester. The crossed Claisen condensation always takes place between the two different carbonyl compounds.

Interpretation Introduction

(b)

Interpretation:

The compounds needed to carry out Step [1] are to be stated.

Concept introduction:

In crossed claisen condensation reaction, the base abstracts the acidic proton from α− carbon atom of an ester to form enolate. This enolate reacts with carbonyl group of other ester that leads to the formation of a β-keto ester. The crossed Claisen condensation always takes place between the two different carbonyl compounds.

Interpretation Introduction

(c)

Interpretation:

The detailed mechanism for step [3] is to be drawn.

Concept introduction:

When only one carbonyl component has an alpha hydrogen atom, then a cross aldol reaction will occur. There will be formation of only one product. The yield of single cross aldol condensation reaction is enhanced if the electrophilic carbonyl compound is relatively unhindered.

Interpretation Introduction

(d)

Interpretation:

The detailed mechanism for step [4] is to be drawn. The reason as to why the product formed is unusual is to be stated.

Concept introduction:

When only one carbonyl component has an alpha hydrogen atom, then a cross aldol reaction will occur. There will be formation of only one product. The yield of single cross aldol condensation reaction is enhanced if the electrophilic carbonyl compound is relatively unhindered.

Interpretation Introduction

(e)

Interpretation:

The reason behind the unnecessary addition and removal of formyl group is to be predicted.

Concept introduction:

When only one carbonyl component has an alpha hydrogen atom, then a cross aldol reaction will occur. There will be formation of only one product. The yield of single cross aldol condensation reaction is enhanced if the electrophilic carbonyl compound is relatively unhindered.

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Answer 3

Question

Chapter 24, Problem 24.68P

Interpretation Introduction

(a)

Interpretation:

The compounds needed to carry out Step [1] are to be stated.

Concept introduction:

In crossed claisen condensation reaction, the base abstracts the acidic proton from α− carbon atom of an ester to form enolate. This enolate reacts with carbonyl group of other ester that leads to the formation of a β-keto ester. The crossed Claisen condensation always takes place between the two different carbonyl compounds.

Interpretation Introduction

(b)

Interpretation:

The compounds needed to carry out Step [1] are to be stated.

Concept introduction:

In crossed claisen condensation reaction, the base abstracts the acidic proton from α− carbon atom of an ester to form enolate. This enolate reacts with carbonyl group of other ester that leads to the formation of a β-keto ester. The crossed Claisen condensation always takes place between the two different carbonyl compounds.

Interpretation Introduction

(c)

Interpretation:

The detailed mechanism for step [3] is to be drawn.

Concept introduction:

When only one carbonyl component has an alpha hydrogen atom, then a cross aldol reaction will occur. There will be formation of only one product. The yield of single cross aldol condensation reaction is enhanced if the electrophilic carbonyl compound is relatively unhindered.

Interpretation Introduction

(d)

Interpretation:

The detailed mechanism for step [4] is to be drawn. The reason as to why the product formed is unusual is to be stated.

Concept introduction:

When only one carbonyl component has an alpha hydrogen atom, then a cross aldol reaction will occur. There will be formation of only one product. The yield of single cross aldol condensation reaction is enhanced if the electrophilic carbonyl compound is relatively unhindered.

Interpretation Introduction

(e)

Interpretation:

The reason behind the unnecessary addition and removal of formyl group is to be predicted.

Concept introduction:

When only one carbonyl component has an alpha hydrogen atom, then a cross aldol reaction will occur. There will be formation of only one product. The yield of single cross aldol condensation reaction is enhanced if the electrophilic carbonyl compound is relatively unhindered.

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Answer 4

Question

Chapter 24, Problem 24.68P

Interpretation Introduction

(a)

Interpretation:

The compounds needed to carry out Step [1] are to be stated.

Concept introduction:

In crossed claisen condensation reaction, the base abstracts the acidic proton from α− carbon atom of an ester to form enolate. This enolate reacts with carbonyl group of other ester that leads to the formation of a β-keto ester. The crossed Claisen condensation always takes place between the two different carbonyl compounds.

Interpretation Introduction

(b)

Interpretation:

The compounds needed to carry out Step [1] are to be stated.

Concept introduction:

In crossed claisen condensation reaction, the base abstracts the acidic proton from α− carbon atom of an ester to form enolate. This enolate reacts with carbonyl group of other ester that leads to the formation of a β-keto ester. The crossed Claisen condensation always takes place between the two different carbonyl compounds.

Interpretation Introduction

(c)

Interpretation:

The detailed mechanism for step [3] is to be drawn.

Concept introduction:

When only one carbonyl component has an alpha hydrogen atom, then a cross aldol reaction will occur. There will be formation of only one product. The yield of single cross aldol condensation reaction is enhanced if the electrophilic carbonyl compound is relatively unhindered.

Interpretation Introduction

(d)

Interpretation:

The detailed mechanism for step [4] is to be drawn. The reason as to why the product formed is unusual is to be stated.

Concept introduction:

When only one carbonyl component has an alpha hydrogen atom, then a cross aldol reaction will occur. There will be formation of only one product. The yield of single cross aldol condensation reaction is enhanced if the electrophilic carbonyl compound is relatively unhindered.

Interpretation Introduction

(e)

Interpretation:

The reason behind the unnecessary addition and removal of formyl group is to be predicted.

Concept introduction:

When only one carbonyl component has an alpha hydrogen atom, then a cross aldol reaction will occur. There will be formation of only one product. The yield of single cross aldol condensation reaction is enhanced if the electrophilic carbonyl compound is relatively unhindered.

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Answer 5

Chapter 24, Problem 24.68P

Interpretation Introduction

(a)

Interpretation:

The compounds needed to carry out Step [1] are to be stated.

Concept introduction:

In crossed claisen condensation reaction, the base abstracts the acidic proton from α− carbon atom of an ester to form enolate. This enolate reacts with carbonyl group of other ester that leads to the formation of a β-keto ester. The crossed Claisen condensation always takes place between the two different carbonyl compounds.

Interpretation Introduction

(b)

Interpretation:

The compounds needed to carry out Step [1] are to be stated.

Concept introduction:

In crossed claisen condensation reaction, the base abstracts the acidic proton from α− carbon atom of an ester to form enolate. This enolate reacts with carbonyl group of other ester that leads to the formation of a β-keto ester. The crossed Claisen condensation always takes place between the two different carbonyl compounds.

Interpretation Introduction

(c)

Interpretation:

The detailed mechanism for step [3] is to be drawn.

Concept introduction:

When only one carbonyl component has an alpha hydrogen atom, then a cross aldol reaction will occur. There will be formation of only one product. The yield of single cross aldol condensation reaction is enhanced if the electrophilic carbonyl compound is relatively unhindered.

Interpretation Introduction

(d)

Interpretation:

The detailed mechanism for step [4] is to be drawn. The reason as to why the product formed is unusual is to be stated.

Concept introduction:

When only one carbonyl component has an alpha hydrogen atom, then a cross aldol reaction will occur. There will be formation of only one product. The yield of single cross aldol condensation reaction is enhanced if the electrophilic carbonyl compound is relatively unhindered.

Interpretation Introduction

(e)

Interpretation:

The reason behind the unnecessary addition and removal of formyl group is to be predicted.

Concept introduction:

When only one carbonyl component has an alpha hydrogen atom, then a cross aldol reaction will occur. There will be formation of only one product. The yield of single cross aldol condensation reaction is enhanced if the electrophilic carbonyl compound is relatively unhindered.

Answer 6

Chapter 24, Problem 24.68P

Interpretation Introduction

(a)

Interpretation:

The compounds needed to carry out Step [1] are to be stated.

Concept introduction:

In crossed claisen condensation reaction, the base abstracts the acidic proton from α− carbon atom of an ester to form enolate. This enolate reacts with carbonyl group of other ester that leads to the formation of a β-keto ester. The crossed Claisen condensation always takes place between the two different carbonyl compounds.

Answer 7

Chapter 24, Problem 24.68P

Interpretation Introduction

(a)

Interpretation:

The compounds needed to carry out Step [1] are to be stated.

Concept introduction:

In crossed claisen condensation reaction, the base abstracts the acidic proton from α− carbon atom of an ester to form enolate. This enolate reacts with carbonyl group of other ester that leads to the formation of a β-keto ester. The crossed Claisen condensation always takes place between the two different carbonyl compounds.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The compounds needed to carry out Step [1] are to be stated.

Concept introduction:

In crossed claisen condensation reaction, the base abstracts the acidic proton from α− carbon atom of an ester to form enolate. This enolate reacts with carbonyl group of other ester that leads to the formation of a β-keto ester. The crossed Claisen condensation always takes place between the two different carbonyl compounds.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The compounds needed to carry out Step [1] are to be stated.

Concept introduction:

In crossed claisen condensation reaction, the base abstracts the acidic proton from α− carbon atom of an ester to form enolate. This enolate reacts with carbonyl group of other ester that leads to the formation of a β-keto ester. The crossed Claisen condensation always takes place between the two different carbonyl compounds.

Answer 10

Interpretation Introduction

(c)

Interpretation:

The detailed mechanism for step [3] is to be drawn.

Concept introduction:

When only one carbonyl component has an alpha hydrogen atom, then a cross aldol reaction will occur. There will be formation of only one product. The yield of single cross aldol condensation reaction is enhanced if the electrophilic carbonyl compound is relatively unhindered.

Answer 11

Interpretation Introduction

(c)

Interpretation:

The detailed mechanism for step [3] is to be drawn.

Concept introduction:

When only one carbonyl component has an alpha hydrogen atom, then a cross aldol reaction will occur. There will be formation of only one product. The yield of single cross aldol condensation reaction is enhanced if the electrophilic carbonyl compound is relatively unhindered.

Answer 12

Interpretation Introduction

(d)

Interpretation:

The detailed mechanism for step [4] is to be drawn. The reason as to why the product formed is unusual is to be stated.

Concept introduction:

When only one carbonyl component has an alpha hydrogen atom, then a cross aldol reaction will occur. There will be formation of only one product. The yield of single cross aldol condensation reaction is enhanced if the electrophilic carbonyl compound is relatively unhindered.

Answer 13

Interpretation Introduction

(d)

Interpretation:

The detailed mechanism for step [4] is to be drawn. The reason as to why the product formed is unusual is to be stated.

Concept introduction:

When only one carbonyl component has an alpha hydrogen atom, then a cross aldol reaction will occur. There will be formation of only one product. The yield of single cross aldol condensation reaction is enhanced if the electrophilic carbonyl compound is relatively unhindered.

Answer 14

Interpretation Introduction

(e)

Interpretation:

The reason behind the unnecessary addition and removal of formyl group is to be predicted.

Concept introduction:

When only one carbonyl component has an alpha hydrogen atom, then a cross aldol reaction will occur. There will be formation of only one product. The yield of single cross aldol condensation reaction is enhanced if the electrophilic carbonyl compound is relatively unhindered.

Answer 15

Interpretation Introduction

(e)

Interpretation:

The reason behind the unnecessary addition and removal of formyl group is to be predicted.

Concept introduction:

When only one carbonyl component has an alpha hydrogen atom, then a cross aldol reaction will occur. There will be formation of only one product. The yield of single cross aldol condensation reaction is enhanced if the electrophilic carbonyl compound is relatively unhindered.

Answer 16

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Answer 17

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Answer 18

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Answer 19

Ch. 24 - Prob. 24.1P Ch. 24 - Prob. 24.2P Ch. 24 - Problem 24.3 What unsaturated carbonyl compound is...Ch. 24 - Acid-catalyzed dehydration of hydroxy carbonyl...Ch. 24 - Prob. 24.5P Ch. 24 - Prob. 24.6P Ch. 24 - Prob. 24.7P Ch. 24 - Problem 24.8 Draw the products formed in the...Ch. 24 - Prob. 24.9P Ch. 24 - Prob. 24.10P

Solution Summary: The author explains that the compounds needed to carry out Step 1 are HCOOEt, NaOEt.

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Chapter 24 Solutions