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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

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Question: When buta-1,3-diene (CH2=CH-CH=CH2) is treated with HBr, two constitutional isomers are formed CH3CHBr-CH=CH2and Br-CH2CH=CHCH2. Draw a stepwise mechanism that accounts for the formation of both products.

Question: Draw the constitutional isomer formed when the following alkenes are treated with each set of reagents: [1] H2O,H2SO4; or [2] BH3followed by H2O2,HO-.

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Question: Explain why the addition of HBr to alkenes A and C is regioselective, forming addition products B and D, respectively.
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