(a)
Interpretation:
It is to be explained whether the given transformation would be a result of acid-catalyzed hydration or oxymercuration-reduction.
Concept introduction:
The acid-catalyzed hydration of an
The oxymercuration-reduction is also the reaction of addition of water through the
Answer to Problem 12.44P
The given transformation can be carried out by oxymercuration-reduction. The detailed mechanism is as follows:
Explanation of Solution
The given equation is
In the substrate, the alkene
The alkene substrate, on reaction with mercury
In the first step, the electron rich
In the second step, the water molecule acts as a nucleophile on one of the carbons of the three-membered ring to open the 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 preparation of the given compound is explained indicating the addition of water across the
(b)
Interpretation:
It is to be explained whether the given transformation would be a result of acid-catalyzed hydration or oxymercuration-reduction.
Concept introduction:
The acid-catalyzed hydration of an alkene is the electrophilic addition of water across the
The oxymercuration-reduction is also the reaction of addition of water through the
Answer to Problem 12.44P
The given transformation can be carried out by acid-catalyzed hydration. The detailed mechanism is as follows:
Explanation of Solution
The given equation is
In the substrate, the alkene
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 more stable tertiary as well as resonance stabilized carbocation by
In the second step, the water molecule acts as a nucleophile on one of the carbons of the three-membered ring to open the ring, followed by deprotonation of the positively charged oxygen atom.
The detailed mechanism for the given reaction is drawn by suggesting that the reaction occurred through carbocation rearrangement.
(c)
Interpretation:
It is to be explained whether the given transformation would be a result of acid-catalyzed hydration or oxymercuration-reduction.
Concept introduction:
The acid-catalyzed hydration of an alkene is the electrophilic addition of water across the
The oxymercuration-reduction is also the reaction of addition of water through the
Answer to Problem 12.44P
The given transformation can be carried out by acid catalyzed hydration. The detailed mechanism is as follows:
Explanation of Solution
The given equation is
In the substrate, the alkene
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 more stable tertiary by
In the second step, the water molecule acts as a nucleophile on one of the carbons of the three-membered ring to open the ring, followed by deprotonation of the positively charged oxygen atom.
The detailed mechanism for the given reaction is drawn by suggesting that the reaction occurred through carbocation rearrangement.
(d)
Interpretation:
It is to be explained whether the given transformation would be a result of acid-catalyzed hydration or oxymercuration-reduction.
Concept introduction:
The acid-catalyzed hydration of an alkene is the electrophilic addition of water across the
The oxymercuration-reduction is also the reaction of addition of water across the
Answer to Problem 12.44P
The given transformation can be carried out by oxymercuration-reduction. The detailed mechanism is as follows:
Explanation of Solution
The given equation is
In the substrate, the alkene
The alkene substrate, on reaction with mercury
In the first step, the electron rich
In the second step, the water molecule acts as a nucleophile on one of the carbons of the three-membered ring to open the 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 preparation of the given compound is explained indicating the addition of water across the
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Chapter 12 Solutions
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