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Chapter 10: PROBLEM 10.59 (page 423)

Question: Draw a stepwise mechanism that shows how all three alcohols are formed from the bicyclic alkene.

Short Answer

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Answer

Step by step solution

01

Stability of carbocation

The formation of the major product of the alkene addition reaction depends on the stability of the carbocation. If the reaction gives secondary and tertiary carbocation intermediates, the tertiary carbocation will form the major product.

02

Explanation

The protonation of alkene occurs in the presence of sulfuric acid to form a secondary carbocation. The tertiary carbocation is generated by 1,2-methyl shift.

The mechanism is shown below:

Reaction mechanism

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Most popular questions from this chapter

Question: Draw a stepwise mechanism for the following reaction. Draw the transition state for each step.

Question: Which alcohols can be prepared as a single product by hydroboration鈥搊xidation of an alkene? Which alcohols can be prepared as a single product by the acid-catalyzed addition of H2O to an alkene?

a.

b.

c.

d.

Question: Give the structure corresponding to each name.

a. (E)-4-ethylhept-3-ene

b. 3,3-dimethylcyclopentene

c. 4-vinylcyclopentene

d. (Z)-3-isopropylhept-2-ene

e. cis-3,4-dimethylcyclopentene

f. 1-isopropyl-4-propylcyclohexene

g. 3,4-dimethylcyclohex-2-enol

h. 3,5-diethylhex-5-en-3-ol

Question: Draw the products of each reaction and indicate their stereochemistry.

Question: (a) Draw all possible stereoisomers of 4-methylnon-2-ene, and name each isomer, including its E, Z and R, S prefixes. (b) Label two pairs of enantiomers. (c) Label four pairs of diastereomers.
See all solutions

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