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Chapter 18: Q70E (page 594)

Predict the product(s) if the starting materials below underwent a Claisen rearrangement. Draw arrows to illustrate the rearrangement of electrons.

(a)

(b)

(c)

Short Answer

Expert verified

The answer is

(a)

(b)

(c)

Step by step solution

01

Claisen rearrangement

The Claisen rearrangement is a reaction of unsaturated compounds that takes place in the presence of heat. It is also called the (3,3) rearrangement.

02

Subpart (a)

The product of the reaction is shown below.

Reaction (a)

The reaction involves the rearrangement of electrons in presence of heat to give an unsaturated cyclic ketone.

03

Subpart (b)

The product of the reaction is shown below.

Reaction (b)

In this reaction, rearrangement gives an unsaturated aldehyde containing Deuterium.

04

Subpart (c)

The product of the reaction is shown below.

Reaction (c)

The reaction involves the rearrangement of the reactant to give a cyclic unsaturated ketone.

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Most popular questions from this chapter

Show the product, including stereochemistry, that would result from reaction of the following epoxide with HBr

In nature, the enzyme chorismate mutase catalyses a Claisen rearrangement of chorismate that involves both the terminal double bond and the double bond with the highlighted carbon. What is the structure of prephenate, the biological precursor to the amino acids phenylalanine and tyrosine?

Chorismate

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.

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.

Name the following ethers:

f)
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