Organic Chemistry As a Second Language: First Semester Topics
Organic Chemistry As a Second Language: First Semester Topics
4th Edition
ISBN: 9781119110668
Author: David R. Klein
Publisher: WILEY
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Chapter 14.3, Problem 14.15P
Interpretation Introduction

Interpretation:

The products that is expected to be formed when the given compound is heated with excess HBr has to be drawn.

Concept Introduction:

Ether are compounds that contain an oxygen atom that is sandwiched between two R groups.  The R groups may be alkyl, vinyl or aryl.

Ethers generally don’t react under mildly acidic or basic conditions.  Under a strong acidic conditions, the CO bonds can undergo cleavage.  When the ether is treated with hydrogen halides, the CO bond undergo acidic cleavage to form two alkyl halides.  The general reaction scheme can be given as,

Organic Chemistry As a Second Language: First Semester Topics, Chapter 14.3, Problem 14.15P , additional homework tip  1

The two alkyl groups are cleaved and alkyl halide is formed as shown above.  In this ether reaction with excess hydrogen halide, few exceptions are there.  The CO bonds that has a sp2 hybridized center cannot be cleaved.  The general scheme can be shown as,

Organic Chemistry As a Second Language: First Semester Topics, Chapter 14.3, Problem 14.15P , additional homework tip  2

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