(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 & MECHANISM
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- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning