(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
Organic Chemistry: Principles and Mechanisms (Second Edition)
- The correct synthesis of octane would involve which of the following reactions?arrow_forwardWrite the reactants and conditions of reaction and the structure of the intermediates A, B, and C that complete the following transformation.arrow_forwardWhich of the following will not undergo catalytic reduction in the presence of H2 and metal catalyst?arrow_forward
- Which of the following is the structure of the rearranged carbocation intermediate in the following dehydration?arrow_forwardProvide the alkene needed to synthesize each of the compounds given by oxymercuration– demercuration. Provide the alkene needed to synthesize each of the compounds given by hydroboration- oxidation.arrow_forwardThe proper reaction scheme by indicating the reactant structure, all necessary reagents, or the major organic product(s) for each indicated transformation.arrow_forward
- For the following reaction scheme, identify by drawing the reagents b and d and the intermediate c that are formed in the synthesis of benzoic acid.arrow_forwardWrite the mechanism, as well as the structure of intermediate A and product B, for the following reaction.arrow_forwardSupply the missing reagent for the following reactions.arrow_forward
- Give the alkene and reagent that are needed to synthesize each of the following compoundsarrow_forwardPlease help me with the question below: For each of the following reactions, state the mechanism the reaction will follow and give the major product(s) of the reaction.arrow_forwardA problem often encountered in the oxidation of primary alcohols to acids is that esters are sometimes produced as by-products. For example, oxidation of ethanol yields acetic acid and ethyl acetate: Propose a mechanism to account for the formation of ethyl acetate. Take into account the reversible reaction between aldehydes and alcohols:arrow_forward