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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°>2°>1°.

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°carbocation. The 3°carbocation forms a tertiary halide product.

The mechanism is shown below:

Reaction mechanism

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Most popular questions from this chapter

Question: Devise a synthesis of each compound from cyclohexene as the starting material. More than one step is needed.

a.

b.

c.

d.

Question: Like other electrophiles, carbocations add to alkenes to form new carbocations, which can then undergo substitution or elimination reactions depending on the reaction conditions. With this in mind, consider the following reactions of nerol, a natural product isolated from lemon grass and other plant sources. Treatment of nerol with TsOH forms α-terpineol as the major product, whereas treatment of nerol with chlorosulfonic acid, HSO3Cl , forms a constitutional isomer, α-cyclogeraniol. Write stepwise mechanisms for both processes. Each mechanism involves the addition of an electrophile—a carbocation— to a double bond.

Question: What stereoisomers are formed when pent-1-ene is treated with H2O and H2SO4?

Question: Draw the products formed when (CH3)2C=CH2 is treated with each reagent.

a. HBr

b.H2O, H2SO4

c. CH3CH2HO,H2SO4

d. Cl2

e.Br2 ,H2O

f. NBS (aqueous DMSO)

g. [1] BH3; [2] H2O2 ,HO-

Question: Draw the products formed when each alkene is treated with BH3followed by H2O2,HO-. Include the stereochemistry at all stereogenic centers.
See all solutions

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