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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

What product would you expect from Claisen rearrangement of 2-butenyl phenyl ether?

Treatment of 1,1-diphenyl-1,2-epoxyethane with aqueous acid yields diphenylacetaldehyde as the major product. Propose a mechanism for the reaction.

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

a.

b.

c.

d.

Acid-catalyzed hydrolysis of a 1,2-epoxycyclohexane produces a transdiaxial 1,2-diol. What product would you expect to obtain from acidic hydrolysis of cis-3-tert-butyl-1,2-epoxycyclohexane? (Recall that the bulky tert-butyl group locks the cyclohexane ring into a specific conformation.)

Fluoxetine, a heavily prescribed antidepressant marketed under the

name Prozac, can be prepared by a route that begins with the reactionbetween a phenol and an alkyl chloride.

  1. The rate of the reaction depends on both phenol and alkyl halide. Is this an SN1 or an SN2 reaction? Show the mechanism.
  2. The physiologically active enantiomer of fluoxetine has (S) stereochemistry. Based on your answer in part (a), draw the structureof the alkyl chloride, you would need, showing the correct stereochemistry.
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