ORGANIC CHEMISTRY-PRINT MULTI TERM
ORGANIC CHEMISTRY-PRINT MULTI TERM
4th Edition
ISBN: 9781119832614
Author: Klein
Publisher: WILEY
Question
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Chapter 12.9, Problem 20ATS

(a)

Interpretation Introduction

Interpretation:

The reaction of PBr3 with the given diol gives a dibromide molecule of which, the structure is to be determined.

Concept Introduction:

Bromination of a diol usually results in the formation of bromide compounds due to nucleophilic substitution reactions. Reactions like these usually follow a mechanism, which usually results in a change in the configuration of the molecule.

(b)

Interpretation Introduction

Interpretation:

A plausible mechanism for the formation of the cyclic ether by-product has to be determined along with the stereochemical justification of the molecule.

Concept Introduction:

Diols when undergoing nucleophilic substitution reactions, sometimes tend to undergo cyclization via intramolecular bonding to form a cyclic ether, under appropriate conditions. Depending upon the type of alcoholic group involved in the formation of the nucleophile, the stereochemical configuration of the product molecule varies.

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