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Chapter 6: Q1P (page 235)

Draw the mechanism for the reaction of cyclohexene with HCl

Short Answer

Expert verified

Cyclohexene is a hydrocarbon that is produced by hydrogenating benzene and is utilised as an industrial intermediate chemical in the production of tetrahydro benzoic acid, adipic acid, and malic acid, as well as in oil extraction.

HCl is a hydrogen halide, while cyclohexene is an alkene. With the addition of an electrophilic reagent, hydrogen halides react with alkene to form alkyl halides.

Step by step solution

01

Definition of cyclohexene-

Cyclohexene is a hydrocarbon that is produced by hydrogenating benzene and is utilised as an industrial intermediate chemical in the production of tetrahydro benzoic acid, adipic acid, and malic acid, as well as in oil extraction.

HCl is a hydrogen halide, while cyclohexene is an alkene. With the addition of an electrophilic reagent, hydrogen halides react with alkene to form alkyl halides.

02

Mechanism for the reaction of cyclohexene with HCl-

The following is the electrophilic addition reaction mechanism for the reaction of cyclohexene with HCl-

Here, cyclohexene has a sp2 carbon, and an electrophile (H+) is added to the sp2 carbon, forming a carbocation intermediate, which reacts quickly with the nucleophile (Cl-) to form an alkyl halide.

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Most popular questions from this chapter

The second-order rate constant (in units of M-1 s-1) for acid-catalysed hydration at 25 掳C is given for each of the following alkenes:

a. Calculate the relative rates of hydration of the alkenes. (Hint: Divide each rate constant by the smallest rate constant of the series: 3.51 脳 10-8.)

b. Why does (Z)-2-butene react faster than (E)-2-butene?

c. Why does 2-methyl-2-butene react faster than (Z)-2-butene?

d. Why does 2,3-dimethyl-2-butene react faster than 2-methyl-2-butene?

What aspect of the structure of the alkene does ozonolysis not tell you ?

a. Is the reaction of 2-butene with HBr regioselective?

b. Is it stereoselective?

c. Is it stereospecific?

d. Is the reaction of 1-butene with HBr regioselective?

e. Is it stereoselective?

f. Is it stereospecific?

When 3-methyl-1-butene reacts with HBr, two alkyl halides are formed: 2-bromo-3-methylbutane and 2-bromo-2-methylbutane. Propose a mechanism that explains the formation of these two products.

a. What alkene would give only a ketone with three carbons as a product of oxidative cleavage?

b. What alkenes would give only an aldehyde with four carbons as a product of oxidative cleavage?
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