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Chapter 16: Q16-20P (page 512)

Styrene, the simplest alkenylbenzene, is prepared commercially for use in plastics manufacture by catalytic dehydrogenation of ethylbenzene. Howmight you prepare styrene from benzene using reactions you’ve studied?

Short Answer

Expert verified

Alkylbenzene is obtained by the FriedelCrafts reaction of benzene with alkylhalide in the presence of AlCl3 .The alkyl group is transformed into an olefinic group by halogenations followed by dehydrohalogenation with alcoholic KOH.

Step by step solution

01

Preparation of alkenylbenzene.

Alkylbenzene is obtained by the FriedelCrafts reaction of benzene with alkylhalide in the presence of AlCl3 .The alkyl group is transformed into an olefinic group by halogenations followed by dehydrohalogenation with alcoholic KOH.

02

Preparation of styrene from benzene 

Benzene undergoes Friedal-Crafts reaction when treated with ethyl chloride in the presence ofAlCl3 to give ethylbenzene. Bromination of ethylbenzene in the benzyl position with NBS results in the formation of bromoethylbenzene which eliminates HBr when treated with ethanolic KOH to produce styrene.

Preparation of styrene from benzene

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Most popular questions from this chapter

The compound MON-0585 is a nontoxic, biodegradable larvicide thatis highly selective against mosquito larvae. Synthesize MON-0585 using either benzene or phenol as a source of the aromatic rings.

Melamine, used as a fire retardant and a component of the writing surface of white boards, can be prepared from s-trichlorotriazine through a series of SNAr reactions with ammonia. The first substitution takes place rapidly at room temperature. The second substitution takes place near 100 °C, and the third substitution requires even higher temperature and pressure. Provide an explanation for this reactivity.

You know the mechanism of HBr addition to alkenes, and you know the effects of various substituent groups on aromatic substitution. Use this knowledge to predict which of the following two alkenes reacts faster with HBr. Explain your answer by drawing resonance structures of the carbocation intermediates.

Question: Identify the reagents represented by the letters a–e in the following scheme:

Rank the compounds in each group according to their reactivity toward electrophilic substitution.

  1. Chlorobenzene, o-dichlorobenzene, benzene
  2. P-bromonitrobenzene, nitrobenzene, phenol
  3. Fluorobenzene, benzaldehyde, o-xylene
  4. Benzonitrile, p-methylbenzonitrile, p-methoxybenzonitrile
See all solutions

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