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Magazine Chapter 12: PROBLEM 12.23 (page 476)
Question: What alkyne (or diyne) yields each set of oxidative cleavage products?
a.
b.
c.
d.
Short Answer
Answer
a.
b.
c.
d.
Step by step solution
Oxidative cleavage
The oxidative cleavage of alkynes is done by reacting them with ozone. The cleavage leads to the formation of two acid groups when the alkyne is internal, and an acid group and carbon dioxide when the alkyne is terminal.
The general reaction of a terminal alkyne and an internal alkyne subjected to ozonolysis is shown below:
Representation of oxidative cleavage of alkynes
Determination of alkynes or diynes
a. Since carbon dioxide is one of the products of oxidative cleavage, we can see that the products have been derived from a terminal alkyne
Determination of the alkyne that led to the following product
b.Since a single type of product is formed, the alkyne which has undergone the oxidative cleavage must be an internal alkyne with similar substitution on both sides.
Determination of the alkyne that led to the following product
c. The three products suggest that they have been produced from a compound having two alkyne groups, that is a diyne.
Determination of the alkyne that led to the following product
d. Since two -COOH groups are formed in a single compound, it can be assumed that the alkyne that has led to this product is present in a ring system and undergoes intramolecular ozonolysis
Determination of the alkyne that led to the following product
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