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 12.7, Problem 12.35P
Interpretation Introduction

Interpretation:

The expected product has to be drawn for the given reaction.

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 12.7, Problem 12.35P , additional homework tip  1

Ozonolysis of Alkynes:

Alkynes undergo ozonolysis with ozone.  The reaction that takes place when an alkyne is treated with ozone is that an oxidative cleavage.  This is followed by treatment with water to give carboxylic acids as products.  If the considered alkyne is an internal alkyne then the product will be two carboxylic acids.  The general scheme can be shown as given below for reaction involving internal alkyne,

Organic Chemistry As a Second Language: First Semester Topics, Chapter 12.7, Problem 12.35P , additional homework tip  2

If the alkyne that is considered is a terminal alkyne, then the terminal end is converted into carbon dioxide and the other end gets converted to carboxylic acid.  The general scheme can be shown for the reaction that involves terminal alkyne is,

Organic Chemistry As a Second Language: First Semester Topics, Chapter 12.7, Problem 12.35P , additional homework tip  3

Expert Solution & Answer
Check Mark

Answer to Problem 12.35P

The expected product is,

Organic Chemistry As a Second Language: First Semester Topics, Chapter 12.7, Problem 12.35P , additional homework tip  4

Explanation of Solution

Given reaction is,

Organic Chemistry As a Second Language: First Semester Topics, Chapter 12.7, Problem 12.35P , additional homework tip  5

From the given reaction condition, it is clear that the given reaction is ozonolysis reaction.  The considered alkyne is an internal alkyne.  Hence, two carboxylic acids will be obtained as products from oxidative cleavage of alkyne.  This can be shown as given below,

Organic Chemistry As a Second Language: First Semester Topics, Chapter 12.7, Problem 12.35P , additional homework tip  6

Conclusion

The expected product was drawn for the given reaction.

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