Concept explainers
Draw the products formed when cholesterol is treated with each reagent. Indicate the stereochemistry around any stereogenic centers in the product.
a.
b.
c. PCC
d. oleic acid,
e. [1]
(a)
Interpretation: The product formed on treatment of cholesterol with
Concept introduction: In the presence of base, the hydroxyl group loses its proton to form alkoxide. The alkoxide attacks on the carbonyl carbon of acyl chloride or anhydride to leading to the formation of acyl group and removal of chloride. This process is known as acylation.
Answer to Problem 31.28P
The product formed on treatment of cholesterol with
Figure 1
Explanation of Solution
In presence of base and acetyl chloride, the hydroxyl group of cholesterol undergoes acetylation. The corresponding chemical reaction is shown below.
Figure 2
The product formed on treatment of cholesterol with
(b)
Interpretation: The product formed on treatment of cholesterol with
Concept introduction: The addition of
Answer to Problem 31.28P
The product formed on treatment of cholesterol with
Figure 3
Explanation of Solution
In presence
Figure 4
The product formed on treatment of cholesterol with
(c)
Interpretation: The product formed on treatment of cholesterol with PCC is to be predicted.
Concept introduction: Alcohols are oxidized to different carbonyl compounds depending upon the reagents and alcohol used. In presence of strong oxidizing reagents such as
Answer to Problem 31.28P
The product formed on treatment of cholesterol with PCC is,
Figure 5
Explanation of Solution
On treatment of cholesterol with PCC, the secondary alcohol is oxidized to ketone. The corresponding chemical reaction is given below
Figure 6
The product formed on treatment of cholesterol with PCC is shown in Figure 5.
(d)
Interpretation: The product formed on treatment of cholesterol with oleic acid,
Concept introduction: In presence of acid, the carboxylic acids are converted to ester using alcohols. This process is known as esterification.
Answer to Problem 31.28P
The product formed on treatment of cholesterol with oleic acid,
Figure 7
Explanation of Solution
In the presence of acid, the hydroxyl group of cholesterol reacts with oleic acid to form ester. The corresponding chemical reaction is shown below.
Figure 8
The product formed on treatment of cholesterol with oleic acid,
(e)
Interpretation: The product formed on treatment of cholesterol with 1.
Concept introduction: In the presence of borane, hydroperoxide and base the alkenes are converted to alcohols. In this reaction hydrogen atom and hydroxyl groups are added to the double bond. This reaction takes place in anti-markovnikov addition manner. This is a syn addition.
Answer to Problem 31.28P
The product formed on treatment of cholesterol with 1.
Figure 9
Explanation of Solution
In the presence of borane, hydroperoxide and base the double bond of cholesterol is oxidized to alcohol. The corresponding chemical reaction is shown below.
Figure 10
The product formed on treatment of cholesterol with 1.
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Chapter 31 Solutions
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