EBK ESSENTIAL ORGANIC CHEMISTRY
EBK ESSENTIAL ORGANIC CHEMISTRY
3rd Edition
ISBN: 8220100659461
Author: Bruice
Publisher: PEARSON
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Chapter 13, Problem 51P

(a)

Interpretation Introduction

Interpretation:

Mechanism of compound are synthesized by the use of only provided carbon-containing compounds has to be given.

Concept introduction:

Required compounds are synthesized by the use of only provided carbon-containing compounds through a series of steps.

In first case, given alcohol is oxidized to a ketone. A strong base is added to the ketone. Aldol condensation reaction takes place. The aldol product is reduced and the final compound is obtained.

In second case, given alcohol is oxidized to a ketone. A strong base is added to the ketone. Aldol condensation reaction takes place. Hydrazine in alcoholic potassium hydroxide is added in the aldol condensation product to remove the carbonyl group. The intermediate alkene is reduced to give the final compound.

In third case, ethanol is oxidized to acetaldehyde. Acetaldehyde undergoes aldol addition reaction in presence of a strong base. Aldol addition product is reduced to form a diol compound 1. Other alcohol is oxidized to an acetone and converted to diol compound 2. Compound 1 and 2 combine to form the final product and two molecules of water are reduced.

(b)

Interpretation Introduction

Interpretation:

Mechanism of compound are synthesized by the use of only provided carbon-containing compounds has to be given.

Concept introduction:

Required compounds are synthesized by the use of only provided carbon-containing compounds through a series of steps.

In first case, given alcohol is oxidized to a ketone.  A strong base is added to the ketone. Aldol condensation reaction takes place. The aldol product is reduced and the final compound is obtained.

In second case, given alcohol is oxidized to a ketone. A strong base is added to the ketone

Aldol condensation reaction takes place. Hydrazine in alcoholic potassium hydroxide is added in the aldol condensation product to remove the carbonyl group. The intermediate alkene is reduced to give the final compound.

In third case, ethanol is oxidized to acetaldehyde.  Acetaldehyde undergoes aldol addition reaction in presence of a strong base. Aldol addition product is reduced to form a diol compound 1. Other alcohol is oxidized to an acetone and converted to diol compound 2. Compound 1 and 2 combine to form the final product and two molecules of water are reduced.

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Hydration of aldehydes and ketones can be catalyzed by acid or base. Bases catalyze hydration by: protonating the carbonyl oxygen making the carbonyl group more electrophilic employing hydroxide ion, which is a better nucleophile than water making the carbonyl group less electrophilic shifting the equilibrium position of the reaction to favor products
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