Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 19, Problem 19.53AP
Interpretation Introduction

(a)

Interpretation:

The mechanism of the given compound which decomposes to acetophenone and HBr is to be stated.

Concept introduction:

The nucleophilic substitution reactions are of two types which are SN1 and SN2. The SN2 reaction is a nucleophilic substitution bimolecular single-step reaction in which the addition of nucleophile and removal of leaving group takes place simultaneously. The SN1 reaction is a nucleophilic substitution reaction in which the substitution of nucleophile takes place. This reaction takes place in two steps. This generates a carbocation intermediate in the reaction.

Interpretation Introduction

(b)

Interpretation:

The given reaction is to be completed with the help of part (a).

Concept introduction:

A glycol is defined as the molecule that contains two hydroxyl groups attached to different carbons. Generally, they are obtained from the oxidation reaction of alkenes. The SN1 reaction is a nucleophilic substitution reaction in which the substitution of nucleophile takes place. This reaction takes place in two steps. This generates a carbocation intermediate in the reaction.

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Propose a mechanism for the reaction of(a) 1-methylcyclohexanol with HBr to form 1-bromo-1-methylcyclohexane.(b) 2-cyclohexylethanol with HBr to form 1-bromo-2-cyclohexylethane.
Please give the main substitution product for each of the following reactions, and indicate the dominant mechanism:      (a)     1-bromopropane   +   NaOCH3   →      (b)     3-bromo-3-methylpentane   +   NaOC2H5   →
3a)Give the mechanisms for the following transformations:

Chapter 19 Solutions

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