Organic Chemistry
Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
Question
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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-ketoester. 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-ketoester. 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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Chapter 24 Solutions

Organic Chemistry

Ch. 24 - Prob. 24.11PCh. 24 - Prob. 24.12PCh. 24 - Prob. 24.13PCh. 24 - Prob. 24.14PCh. 24 - Problem 24.16 What ester is formed when each...Ch. 24 - What crossed Claisen product is formed from each...Ch. 24 - Prob. 24.17PCh. 24 - Draw the products of each reaction. a. b. Ch. 24 - Problem 24.20 Two steps in a synthesis of the...Ch. 24 - Prob. 24.20PCh. 24 - Problem 24.22 Which of the following compounds can...Ch. 24 - What product is formed when each pair of compounds...Ch. 24 - Problem 24.24 What starting materials are needed...Ch. 24 - Problem 24.25 Draw the products when each pair of...Ch. 24 - Problem 24.27 What starting materials are needed...Ch. 24 - Prob. 24.26PCh. 24 - 24.29 What steps are needed to convert A to B? Ch. 24 - Prob. 24.28PCh. 24 - Prob. 24.29PCh. 24 - 24.31 Draw the product formed in each directed...Ch. 24 - Prob. 24.31PCh. 24 - What starting materials are needed to synthesize...Ch. 24 - Prob. 24.33PCh. 24 - Prob. 24.34PCh. 24 - Prob. 24.35PCh. 24 - 24.36 Identify the structures of C and D in the...Ch. 24 - Prob. 24.37PCh. 24 - Prob. 24.38PCh. 24 - Prob. 24.39PCh. 24 - Draw the product formed from a Claisen reaction...Ch. 24 - Prob. 24.41PCh. 24 - 24.41 Even though B contains three ester groups, a...Ch. 24 - Prob. 24.43PCh. 24 - What starting materials are needed to prepare each...Ch. 24 - 24.44 Vetivone is isolated from vetiver, a...Ch. 24 - Draw the product of each Robinson annulation from...Ch. 24 - Prob. 24.47PCh. 24 - Draw the organic products formed when butanal...Ch. 24 - 24.47 Draw the organic products formed in each...Ch. 24 - 24.48 Fill in the lettered reagents needed for...Ch. 24 - Prob. 24.51PCh. 24 - Prob. 24.52PCh. 24 - Prob. 24.53PCh. 24 - Draw a stepwise mechanism for the following...Ch. 24 - Prob. 24.55PCh. 24 - Prob. 24.56PCh. 24 - Prob. 24.57PCh. 24 - Prob. 24.58PCh. 24 - Prob. 24.59PCh. 24 - Prob. 24.60PCh. 24 - Prob. 24.61PCh. 24 - Prob. 24.62PCh. 24 - Devise a synthesis of each compound from...Ch. 24 - Prob. 24.64PCh. 24 - Prob. 24.65PCh. 24 - Prob. 24.66PCh. 24 - 24.65 Answer the following questions about...Ch. 24 - Prob. 24.68PCh. 24 - Prob. 24.69PCh. 24 - Prob. 24.70PCh. 24 - Prob. 24.71PCh. 24 - 24.70 Draw a stepwise mechanism for the following...Ch. 24 - Prob. 24.73PCh. 24 - Prob. 24.74PCh. 24 - Prob. 24.75P
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