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Chapter 18: 29 P (page 711)

How could you use ethylbenzene to prepare each compound? More than one step is required.

Short Answer

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d)

Step by step solution

01

Significance of radical bromination of alkylbenzenes

Benzylic halides are formed as a result of the radical bromination of alkylbenzenes. Benzylic halides are useful as a starting material (reactant) in forming new substituted benzene products.

02

Synthesis using ethyl benzene

a. Bromination of benzylic bromide followed by elimination of HBr gives 2-bromostyrene.


b. Bromination of ethylbenzene followed by elimination of NaBr gives phenyl ethanol.


c. Epoxidation of styrene gives styrene oxide.


d. Hydroboration followed by oxidation of styrene forms phenyl ethyl alcohol.

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Most popular questions from this chapter

Question: Explain the reactivity and orientation effects observed in each heterocycle.

a. Pyridine is less reactive than benzene in electrophilic aromatic substitution and yields 3-substituted products.

b. Pyrrole is more reactive than benzene in electrophilic aromatic substitution and yields 2-substituted products.

Draw the products of each reaction.

Draw the products formed when each compound is treated with HNO3 and H2SO4. State whether the reaction occurs faster or slower than a similar reaction with benzene.

Draw a stepwise mechanism for the following reaction.

Question: Devise a synthesis of optically active (S)-fluoxetine (trade name Prozac) from the given starting materials and any other needed reagents.
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