Essential Organic Chemistry (3rd Edition)
Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 13, Problem 44P

(a)

Interpretation Introduction

Interpretation:

The product of given reactions has to be drawn.

Concept introduction:

Malonic ester synthesis is used to prepare carboxylic acids of the desired length.  The malonic ester is reacted with an alkoxide base which removes a alpha hydrogen.

The anion so formed is reacted with an alkyl halide.  The anion abstracts the alkyl group from the alkyl halide.  On heating, decarboxylation takes place which gives the desired carboxylic acid.

Aldol reaction is an addition reaction of aldehydes and ketones.  Aldol reaction is a reversible reaction and occurs in the presence of a strong base like sodium hydroxide.

One molecule (aldehyde or ketone) acts a nucleophile and attacks the electrophilic carbon center of the other molecule to give the addition product.  The product is named β-hydroxy aldehyde if two aldehydes combine and β-hydroxy ketone if two ketones combine.

(b)

Interpretation Introduction

Interpretation:

 The product of given reactions has to be drawn.

Concept introduction:

Malonic ester synthesis is used to prepare carboxylic acids of the desired length.  The malonic ester is reacted with an alkoxide base which removes a alpha hydrogen.

The anion so formed is reacted with an alkyl halide. The anion abstracts the alkyl group from the alkyl halide.  On heating, decarboxylation takes place which gives the desired carboxylic acid.

Aldol reaction is an addition reaction of aldehydes and ketones.  Aldol reaction is a reversible reaction and occurs in the presence of a strong base like sodium hydroxide.

One molecule (aldehyde or ketone) acts a nucleophile and attacks the electrophilic carbon center of the other molecule to give the addition product.  The product is named β-hydroxy aldehyde if two aldehydes combine and β-hydroxy ketone if two ketones combine.

(c)

Interpretation Introduction

Interpretation:

The product of given reactions has to be drawn.

Concept introduction:

Base abstracts a proton and formed enolate will attack the carbon to which halogen is attached, which in turn leads to the removal of halide ion.

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Chapter 13 Solutions

Essential Organic Chemistry (3rd Edition)

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