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Chapter 11: Q12P (page 557)

Propose a mechanism for the reaction of

(a) 1-methyl cyclohexanol with HBr to form 1- bromo-1-methylcyclohexane.

(b) 2- cyclohexylethanol with HBr to form 1-bromo-2-cyclohexylethane.

Short Answer

Expert verified

1-methyl cyclohexanol is tertiary alcohol; thus, it will react with HBr by the SN1 mechanism.

Protonation of 1-methyl cyclohexanol converts the hydroxy group to a good leaving group.

Water leaves, forming a carbocation.

Bromide ion attacks the carbocation to form the product 1- bromo-1-methylcyclohexane.

Mechanism of formation of 1- bromo-1-methylcyclohexane

Step by step solution

01

Formation of 1- bromo-1-methylcyclohexane from 1-methyl cyclohexanol

1-methyl cyclohexanol is tertiary alcohol; thus, it will react with HBr by the SN1 mechanism.

Protonation of 1-methyl cyclohexanol converts the hydroxy group to a good leaving group.

Water leaves, forming a carbocation.

Bromide ion attacks the carbocation to form the product 1- bromo-1-methylcyclohexane.

Mechanism of formation of 1- bromo-1-methylcyclohexane

02

 Formation of 1-bromo-2-cyclohexylethane from 2- cyclohexylethanol

2 - cyclohexylethanol is the primary alcohol that reacts with HBr by the SN2 mechanism.

Protonation of 2- cyclohexylethanol converts the hydroxy group to a good leaving group.

Bromide displaces water to give the product 1-bromo-2-cyclohexylethane.

Mechanism of formation of 1-bromo-2-cyclohexylethane

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Most popular questions from this chapter

When cis-2-methylcyclohexanol reacts with the Lucas reagent, the major product is 1-chloro-1-methylcyclohexane. Propose a mechanism to explain the formation of this product.

Predict the major products of the following reactions.

(a)ethyl tosylate+potassium tert-butoxide

(b) isobutyl tosylate + NaI

(c) (R)-2-hexyl tosylate + NaCN

(d) the tosylate of cyclohexylmethanol +excess NH3

When 1-cyclohexylethanol is treated with concentrated aqueous, the major product is 1-bromo-1-ethylcyclohexane.

(a)Propose a mechanism for this reaction.

(b) How would you convert 1-cyclohexylethanol to (1-bromoethyl)cyclohexane in good yield?

Show how you would use a simple chemical test to distinguish between the following pairs of compounds. Tell what you would observe with each compound.

(a)isopropyl alcohol andtert-butyl alcohol

(b)isopropyl alcohol and butan-2-one, CH3COCH2CH3

(c)hexan-1-ol and cyclohexanol

(d)allyl alcohol and propan-1-ol

(e)butan-2-one andtert-butyl alcohol

Show how you would accomplish the following synthetic conversions

(a)

(b)

(c)

(d)
See all solutions

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