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Chapter 10: PROBLEM 10.56 (page 423)

Question: Draw a stepwise mechanism for the following reaction.

Short Answer

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Answer

Step by step solution

01

Stability of carbocation  

Carbocations are the intermediates formed in the addition reaction of alkenes.

The stability order of carbocations is 3掳>2掳>1掳.

02

1,2-hydrogen shift

The stability of carbocations is the reason for 1,2-hydrogen shift. After the shift of hydrogen to the adjacent position, the carbocation is generated, which is more stable.

03

Explanation

The reaction of the given compound with HBr proceeds via 1,2-hydrogen shift to generate a 3掳carbocation. The 3掳carbocation forms a tertiary halide product.

The mechanism is shown below:

Reaction mechanism

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Most popular questions from this chapter

Question: Use the Hammond postulate to explain why (CH3)2C=CH2reacts faster than CH3CH=CH2 in electrophilic addition of HX.

Question: Which alkene reacts faster with HBr? Explain your choice

Question: Lactones, cyclic esters such as compound A, are prepared by halolactonization, an addition reaction to an alkene. For example, iodolactonization of B forms lactone C, a key intermediate in the synthesis of prostaglandin (Section 4.15). Draw a stepwise mechanism for this addition reaction.

Question: Draw the products of each elimination reaction.

Question: Draw all stereoisomers formed in each reaction.
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