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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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Some alcohols undergo rearrangement or other unwanted side reactions when they dehydrate in acid. Alcohols may be dehydrated under mildly basic conditions using phosphorus oxy-chloride (POCl3) in pyridine. The alcohol reacts with phosphorus oxychlorides much like it reacts with tosyl chloride (Section 11-5), displacing a chloride ion from phosphorus to give an alkyl dichlorophosphate ester. The dichlorophosphate group is an outstanding leaving group. Pyridine reacts as a base with the dichlorophosphate ester to give an E2 elimination. Propose a mechanism for the dehydration of cyclohexanol by POCl3 in pyridine.

Explain the products observed in the following reaction of an alcohol with the Lucas reagent.
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