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 12.2, Problem 12.8P
Interpretation Introduction

Interpretation:

The major product for the given reaction sequence has to be predicted.

Concept Introduction:

Alkynes are the compounds that contain a triple bond between two carbon atoms.  The carbon atom present in the triple bond is sp hybridised.  Due to this, the geometry of alkyne will be linear.  Terminal alkyne are the one which has a proton attached to the triple bond and internal alkyne are the one in which there are no protons attached to the triple bond.

Organic Chemistry As a Second Language: First Semester Topics, Chapter 12.2, Problem 12.8P , additional homework tip  1

Alkynes can be prepared from geminal dihalide or vicinal dihalide by treating with a very strong base.

Organic Chemistry As a Second Language: First Semester Topics, Chapter 12.2, Problem 12.8P , additional homework tip  2

Two equivalents of base is required because the substrate is a dihalide.  If the alkyne formed is a terminal alkyne, then three equivalents of base has to be used resulting in salt formation of the alkyne.  This on treatment with water gives the terminal alkyne.  The general reaction can be given as shown below,

Organic Chemistry As a Second Language: First Semester Topics, Chapter 12.2, Problem 12.8P , additional homework tip  3

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