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Chapter 18: 18-18-8P (page 575)

Write the mechanism of the acid-induced cleavage of tert-butyl cyclohexyl ether to yield cyclohexanol and 2-methylpropene.

Short Answer

Expert verified

The mechanism of the acid-induced cleavage of tert-butyl cyclohexyl ether is,

Step by step solution

01

Acid-induced cleavage of ether

In acid-induced cleavage of ether, ether is treated with strong acid.It generates oxonium ion, collapsing to form an alcohol and a tertiary carbocation which further forms an alkene.

02

Explanation for the mechanism of the reaction

In the acid-catalyzed ether cleavage, the first step is the protonation of ether oxygen, forming an intermediate oxonium ion. This ion collapses to form an alcohol and a tertiary carbocation.

An alkene 2-methylpropene is formed when a carbocation loses a proton. This reaction is an example of E1 elimination. The acid used for the cleavage is often trifluoroacetic acid. The products obtained arecyclohexanol and 2-methylpropene.

03

The mechanism of the reaction

The mechanism of the acid-induced cleavage of tert-butyl cyclohexyl ether is shown below,

The mechanism of the reaction

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Most popular questions from this chapter

Treatment of trans-2-chlorocyclohexanol with NaOH yields 1,2-epoxycyclohexane,but reaction of the cis isomer under the same conditionsyields cyclohexanone. Propose mechanisms for both reactions, andexplain why the different results are obtained.

How would you prepare the following ethers using a Williamson synthesis?

  1. Methyl propyl ether
  2. Anisole (methyl phenyl ether)
  3. Benzyl isopropyl ether
  4. Ethyl 2,2-dimethylpropyl ether

Aldehydes and ketones undergo acid-catalyzed reaction with alcoholsto yield hemiacetals,compounds that have one alcohol-like oxygenand one ether-like oxygen bonded to the same carbon. Further reactionof a hemiacetal with alcohol then yields an acetal,a compound that hastwo ether-like oxygens bonded to the same carbon.

(a)Show the structures of the hemiacetal and acetal you would obtainby reaction of cyclohexanone with ethanol.

(b)Propose a mechanism for the conversion of a hemiacetal into anacetal.

Identify the reagents a-e in the following scheme:

Give IUPAC names for the following structures:
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