
Concept explainers
Draw the products formed when each diene is treated with one equivalent of
a. b.
c.
d.

(a)
Interpretation: The product formed by the reaction of given diene with one equivalent of
Concept introduction: Diene is a hydrocarbon that contains two
Answer to Problem 16.16P
The product formed by the reaction of given diene with one equivalent of
Explanation of Solution
Conjugated dienes undergoes electrophilic addition to gives a mixture of products that is
Markovnikov addition of
The given diene is shown below.
Figure 1
The given diene is a conjugated diene. The attack of
Figure 2
In the next step, chlorine as a nucleophile will attack on the carbocation to give constitutional isomers. Thus, the product formed by the reaction of given diene with one equivalent of
Figure 3
The product formed by the reaction of given diene with one equivalent of

(b)
Interpretation: The product formed by the reaction of given diene with one equivalent of
Concept introduction: Diene is a hydrocarbon that contains two
Answer to Problem 16.16P
The product formed by the reaction of given diene with one equivalent of
Explanation of Solution
Conjugated dienes undergoes electrophilic addition to gives a mixture of products that is
Markovnikov’s rule states that the positive part of acid attached to that carbon atom in
The given diene is shown below.
Figure 4
The given diene is an isolated diene. The attack of
Figure 5
In the next step, chlorine as a nucleophile will attack on the carbocation to form desired product. Thus, the product formed by the reaction of given diene with one equivalent of
Figure 6
The product formed by the reaction of given diene with one equivalent of

(c)
Interpretation: The product formed by the reaction of given diene with one equivalent of
Concept introduction: Diene is a hydrocarbon that contains two
Answer to Problem 16.16P
The product formed by the reaction of given diene with one equivalent of
Explanation of Solution
Conjugated dienes undergoes electrophilic addition to gives a mixture of products that is
Markovnikov addition of
The given diene is shown below.
Figure 7
The given diene is a conjugated diene. The attack of
Figure 8
In the next step, chlorine as a nucleophile will attack on the carbocation to give constitutional isomers. Thus, the product formed by the reaction of given diene with one equivalent of
Figure 9
The product formed by the reaction of given diene with one equivalent of

(d)
Interpretation: The product formed by the reaction of given diene with one equivalent of
Concept introduction: Diene is a hydrocarbon that contains two
Answer to Problem 16.16P
The product formed by the reaction of given diene with one equivalent of
Explanation of Solution
Conjugated dienes undergoes electrophilic addition to gives a mixture of products that is
Markovnikov addition of
The given diene is shown below.
Figure 10
The given diene is a conjugated diene. The attack of
Figure 11
In the next step, chlorine as a nucleophile will attack on the carbocation to give constitutional isomers. Thus, the product formed by the reaction of given diene with one equivalent of
Figure 12
The product formed by the reaction of given diene with one equivalent of
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Chapter 16 Solutions
Organic Chemistry
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