Organic Chemistry - Standalone book
Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 21, Problem 32P
Interpretation Introduction

Interpretation:

An explanation corresponding to ‘the racemization of (R)-()-Piperitone in a solution of sodium ethoxide in ethanol’ and ‘the conversion of menthone to a mixture of menthone and isomenthone on treatment with 90% sulfuric acid’ are to be stated.

Concept introduction:

The mixture that has equal number of enantiomers is commonly known as racemic mixture. The racemic mixture is optically inactive in nature.

Enantiomers are non-superimposable mirror images of each other and therefore; they rotate the plane of polarized light in equal and opposite direction.

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(a) Account for the following :(i) Propanal is more reactive than propanone towards nucleophilic reagents.(ii) Electrophilic substitution in benzoic acid takes place at meta position.(iii) Carboxylic acids do not give characteristic reactions of carbonyl group.(b) Give simple chemical test to distinguish between the following pairs of compounds:(i) Acetophenone and benzaldehyde(ii) Benzoic acid and ethylbenzoate.
(a) How will you convert the following :(i) Propanone to Propan-2-ol                (ii) Ethanal to 2-hydroxy propanoic acid(iii) Toluene to benzoic acid(b) Give simple chemical test to distinguish between :(i) Pentan-2-one and Pentan-3-one       (ii) Ethanal and Propanal
Nucleophilic aromatic substitution provides one of the common methods for making phenols. Show how you would synthesize the following phenols, using benzene or toluene as your aromatic starting material, and explain why mixtures of products would be obtained in some cases.(a) p-nitrophenol (b) 2,4,6-tribromophenol (c) p-chlorophenol

Chapter 21 Solutions

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