Concept explainers
(a)
Interpretation:
Complete
Concept introduction:
A bimolecular nucleophilic substitution (
Answer to Problem 8.43P
Complete
(i)
(ii)
(iii)
(iv)
(v)
Explanation of Solution
(i)
The given reaction is
In the above reaction,
(ii)
The given reaction is
In the above reaction,
The stereochemistry of another group
(iii)
The given reaction
In the above reaction,
The stereochemistry of another group
(iv)
The given reaction
In the above reaction,
The stereochemistry of another group
(v)
The given reaction
In the above reaction,
Another group
The Product of
(b)
Interpretation:
Complete
Concept introduction:
A unimolecular nucleophilic substitution (
If
Answer to Problem 8.43P
Complete
(i)
(ii)
(iii)
(iv)
(v)
Explanation of Solution
(i)
The given reaction is
The leaving group in the above reaction is present on the plane of the planar, no stereochemistry is mentioned. Therefore, stereochemistry is not concerned at C, and the only isomer formed is the one shown in the above diagram.
(ii)
The given reaction is
In the above reaction, leaving group (I) is present above the plane of the paper, thus the nucleophile attacks from both sides of the paper- behind the paper and in front of the paper resulting in the formation of two stereoisomers as shown above.
(iii)
The given reaction
In the above reaction, leaving group (I) is present behind the plane of the paper, thus the nucleophile attacks from both sides of the paper- behind the paper and in front of the paper resulting in the formation of two stereoisomers as shown above.
(iv)
The given reaction
In the above reaction, the carbocation is stabilized by proton transfer. The new carbocation formed at the adjacent carbon from the leaving group is a more stable carbocation. The stereochemistry at the carbon (more stable carbocation) is of no concern. Therefore, the only isomer formed is as shown above.
(v)
The given reaction
In the above reaction, chiral carbocation is formed once the leaving group leaves. Therefore, the nucleophile can attack from either side- from behind the paper and in front of the paper resulting in the formation of two stereoisomers as shown above.
Product of
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Chapter 8 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
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