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Chapter 18: 18-18-7P a (page 575)

Predict the products of the following reactions:

a)

Short Answer

Expert verified

a) The product of the reaction is,


Step by step solution

01

Ether cleavage reaction

In a ether cleavage reaction, the substitution pattern of the two groups attached to an oxygen atom is identified first.In the case of the tertiary alkyl group, the cleavage takes place by SN1 mechanism.

02

The product of the reaction

a)

At first, the substitution pattern of the ether is noticed. On one side of the ether oxygen, is the primary alkyl group and on the other side is the tertiary alkyl group. When the one group is tertiary, the cleavage takes place by an SN1 or E1 route, and it forms either a tertiary halide, an alkene and a primary alcohol.


Product of the reaction

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Most popular questions from this chapter

Name the following ethers:

f)

Propose structures for compounds that have the following 1H NMR spectra:

(a) C5H12S (An –SH proton absorbs near 1.6δ)

(b)C9H11BRO

(c)C5H12O2

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.

How would you synthesize anethole (Problem 18-54) from phenol?

Predict the products of the following ether cleavage reactions:
See all solutions

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