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Chapter 11: Q17P (page 559)

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.

Short Answer

Expert verified

Lucas reagent is the chemical solution of zinc chloride ( ZnCl2 ) and concentrated hydrochloric acid (HCl), which as a chlorinating agent replaces the hydroxyl group in alcohol with a chlorine atom.

Alcohol is soluble in the Lucas reagent, while the alkyl chloride formed is not soluble in the Lucas reagent.

Step by step solution

01

Lucas reagent

Lucas reagent is the chemical solution of zinc chloride ( ZnCl2 ) and concentrated hydrochloric acid (HCl), which as a chlorinating agent replaces the hydroxyl group in alcohol with a chlorine atom.

Alcohol is soluble in the Lucas reagent, while the alkyl chloride formed is not soluble in the Lucas reagent.

02

Step 2: Mechanism of formation of 1-chloro-1-methylcyclohexane

Cis -2-methyl-cyclohexanol When reacted with Lucas reagent converts the hydroxy group to a good leaving group.

Good leaving group leaves, forming a 20 carbocation which rearranges by hydride shift forming a stable 30 carbocation

Chloride ion attacks the carbocation to form the product 1-chloro-1-methylcyclohexane.

Mechanism of forming 1-chloro-1-methylcyclohexane

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Most popular questions from this chapter

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.

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?

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A student wanted to use the Williamson ether synthesis to make (R)-2-ethoxybutane. He remembered that the Williamson synthesis involves an SN2 displacement, which takes place with inversion of configuration. He ordered a bottle of (S)-butan-2-ol for his chiral starting material. He also remembered that the SN2goes best on primary halides and tosylates, so he made ethyl tosylate and sodium (S)-but-2-oxide. After warming these reagents together, he obtained an excellent yield of 2-ethoxybutane.

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