(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)
- For each of the following reactions draw the structure of the major organic product in the box provided.Each numbered set of reagents above or below the arrow represents a complete separate reaction.For multi-step reactions give only the structure of the final product.arrow_forwardDraw a detailed mechanism for the following reaction and include the major productarrow_forwardSubmit the mechanism for the following reaction. Use the mechanism you draw to match this reaction with the correct energy diagram.arrow_forward
- . Use to curved arrow notation, propose a mechanism for the following reaction and state whether it is either SN1, E1, SN2, or E2. Give the IUPAC names of all organic reactants and products.arrow_forwardDraw the organic products in each of the following reactions.arrow_forwardplease help with this question thank you. Draw the mechanism for the reaction given.arrow_forward
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