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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

Treatment of the following alkene with a peroxy acid yields an epoxide different from that obtained by reaction with aqueous Br2 followed by base treatment. Propose structures for the two epoxides, and explain the result.

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

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.

Give IUPAC names for the following structures:

Griginard reagents react with oxetane, a four membered cyclic ether, to yield primary alcohols, but the reaction is much slower than the corresponding reaction with ethylene oxide. Suggest a reason for the difference in reactivity between oxetane and ethylene oxide.

Oxetane
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