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Chapter 20: Q13P (page 1038)

The reaction of tert-butyl alcohol with concentrated HCl goes by the SN1 mechanism. Write a mechanism for this reaction.

Short Answer

Expert verified

In a Unimolecular nucleophile substitution ( SN1 ) reaction, only one molecule (carbocation formation) is involved in the 鈥渞ate-determining step.鈥�

Unimolecular nucleophilic substitution is also known as a first-order reaction.

Hydrolysis of tertiary alkyl halide follows a Unimolecular nucleophilic substitution reaction.

Step by step solution

01

Unimolecular Nucleophilic substitution Reaction ( SN1 )

In a Unimolecular nucleophile substitution ( SN1 ) reaction, only one molecule (carbocation formation) is involved in the 鈥渞ate-determining step.鈥�

Unimolecular nucleophilic substitution is also known as a first-order reaction.

Hydrolysis of tertiary alkyl halide follows a Unimolecular nucleophilic substitution reaction.

02

Formation of 1- bromo-1-methylcyclohexane from tert-butyl alcohol

tert-butyl alcoholis tertiary alcohol; thus, it will react with HCl by the SN1 mechanism.

Protonation of tert-butyl alcoholconverts the hydroxy group to a good leaving group.

Water leaves, forming a carbocation.

Bromide ion attacks the carbocation to form the product 2-chloro-2-methylpropane.

Mechamism of forming 2-chloro-2-methylpropane

Mechanism of formation of 1- bromo-1-methylcyclohexane

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