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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 the isomers for the following compounds and then name each one:

a. 2-methyl-2,4-hexadiene

b. 2,4-heptadiene

c. 1,3-pentadiene

Question: Give the IUPAC name for each alkene.

Question: Draw a stepwise mechanism for the following reaction, which results in ring expansion of a six-membered ring to a seven-membered ring.

Question: What alkene can be used to prepare each alcohol as the exclusive product of a two-step hydroboration–oxidation sequence?

Question: Label each C-C double bond as E or Z. Kavain is a naturally occurring relaxant isolated from kava root.
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