EBK ORGANIC CHEMISTRY
EBK ORGANIC CHEMISTRY
6th Edition
ISBN: 8220103151757
Author: LOUDON
Publisher: MAC HIGHER
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Chapter 10, Problem 10.49AP
Interpretation Introduction

(a)

Interpretation:

The mechanism of conversion of enantiomerically pure (R)-CH3CH2CHDOH into (S)-CH3CH2CHD18OH is to be stated.

Concept introduction:

Substitution reaction is one of the types of reaction in which one species is replaced by the other species. Substitution reactions can be done either by SN1 mechanism or by SN2 mechanism. Inversion of the stereochemistry of the product from reactant takes place in SN2 mechanism.

Interpretation Introduction

(b)

Interpretation:

The mechanism of conversion of enantiomerically pure (R)-CH3CH2CHDOH into (R)-CH3CH2CHD18OH is to be stated.

Concept introduction:

Substitution reaction is one of the types of reaction in which one species is replaced by the other species. Substitution reactions can be done either by SN1 mechanism or by SN2 mechanism. Inversion of the stereochemistry of the product from reactant takes place in SN2 mechanism.

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Give reasons for the following :(i) Ethyl iodide undergoes SN2 reaction faster than ethyl bromide.(ii) (±) 2-Butanol is optically inactive.(iii) C—X bond length in halobenzene is smaller than C—X bond length in CH3—X.
(a) How will you convert:(i) Benzene to acetophenone                 (ii) Propanone to 2-Methylpropan-2-ol(b) Give reasons :(i) Electrophilic substitution in benzoic acid takes place at meta position.(ii) Carboxylic acids are higher boiling liquids than aldehydes, ketones and alcohols of comparable molecular masses.(iii) Propanal is more reactive than propanone in nucleophilic addition reactions.
(c) Hydrolysis of the haloalkane shown below results in the formation of two alcohols B and C that are stereoisomers of each other. Give the structures of the alcohols B and C and propose a mechanism for their formation ensuring that you explain the stereochemical outcome observed. H3CH2C CH3 H20, heat Br B + C

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EBK ORGANIC CHEMISTRY

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