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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

Predict the product(s) and provide the mechanism for each reaction below. What do the mechanisms have in common?

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b.

c.

d.

2-Butene-1-thiol is one component of skunk spray. How would you synthesize this substance from methyl 2-butenoate? From 1,3-butadiene?

Predict the products of the following reactions:

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(b)

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Rank the following halides in order of their reactivity in Williamson synthesis:

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  2. Chloroethane, bromoethane, 1-iodopropene

Imagine that you have created (2R, 3R)-2,3-epoxy-3-methylpentane with aqueous acid to carry out a ring opening reaction.

  1. Draw the epoxide showing stereochemistry.
  2. Draw and name the product showing stereochemistry.
  3. Is the product chiral? Explain.
  4. Is the product optically active? Explain.
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