
(a)
Interpretation:
The detailed mechanism with the major product for the given reaction is to be drawn.
Concept introduction:
The acid-catalyzed hydration of an

Answer to Problem 12.42P
The detailed mechanism for the given reaction is
Explanation of Solution
The given reaction is
Cyclopentylethene, a terminal alkene, in presence of
The first step is the formation of a secondary carbocation by proton transfer reaction. The proton transfers to the less substituted double bonded carbon.
The secondary carbocation can be rearranged to a more stable tertiary carbocation by
In the second step, the water molecule acts as a nucleophile and attacks the tertiary carbocation, forming a tertiary alcohol product, followed by deprotonation of the positively charged oxygen.
The detailed mechanism for the given reaction is drawn by suggesting that the reaction occurs through carbocation rearrangement.
(b)
Interpretation:
The detailed mechanism with major product for the given reaction is to be drawn.
Concept introduction:
The oxymercuration-reduction is also the reaction of addition of water across the

Answer to Problem 12.42P
The detailed mechanism for the given reaction is
Explanation of Solution
The given reaction is
Cyclopentylethene, a terminal alkene, on reaction with mercury
In the first step, the electron rich
In the second step, the water molecule acts as a nucleophile and, according to Markovnikov rule, attacks the most substituted side to open the three-membered ring, followed by deprotonation of the positively charged oxygen atom.
The product formed in the previous step is then subjected to reduction with sodium borohydride,
The detailed mechanism for the given reaction is drawn by suggesting that the reaction occurred through formation of mercurinium ion intermediate without rearrangement.
(c)
Interpretation:
The detailed mechanism with major product for the given reaction is to be drawn.
Concept introduction:
The acid-catalyzed hydration of an alkene is the electrophilic addition of water across the

Answer to Problem 12.42P
The detailed mechanism for the given reaction is
Explanation of Solution
The given reaction is
The given substrate, a terminal alkene, in the presence of
The first step is the formation of a secondary carbocation by proton transfer reaction. The proton transfers to the less substituted double bonded carbon.
The secondary carbocation can be rearranged to a more stable tertiary as well as resonance stabilized carbocation by
In the second step, the water molecule acts as a nucleophile and attacks the tertiary carbocation, forming a tertiary alcohol product, followed by deprotonation of the positively charged oxygen.
The detailed mechanism for the given reaction is drawn by suggesting that the reaction occurred through carbocation rearrangement.
(d)
Interpretation:
The detailed mechanism with major product for the given reaction is to be drawn.
Concept introduction:
The oxymercuration-reduction is also the reaction of addition of water across the

Answer to Problem 12.42P
The detailed mechanism for the given reaction is
Explanation of Solution
The given reaction is
The given substrate, a terminal alkene, on reaction with mercury
In the first step, the electron rich
In the second step, the water molecule acts as a nucleophile and, according to Markovnikov rule, attacks the most substituted side to open the three-membered ring, followed by deprotonation of the positively charged oxygen atom.
The product formed in the previous step is then subjected to reduction with sodium borohydride,
The detailed mechanism for the given reaction is drawn by suggesting that the reaction occurred through formation of mercurinium ion intermediate without rearrangement.
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Chapter 12 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
- What is the name of the following compound? SiMe3arrow_forwardK Draw the starting structure that would lead to the major product shown under the provided conditions. Drawing 1. NaNH2 2. PhCH2Br 4 57°F Sunny Q Searcharrow_forward7 Draw the starting alkyl bromide that would produce this alkyne under these conditions. F Drawing 1. NaNH2, A 2. H3O+ £ 4 Temps to rise Tomorrow Q Search H2arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
