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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

Name and draw the major product (s) of electrophilic chlorination of the following compounds:

  1. m-nitrophenol
  2. o-xylene
  3. p-nitrobenzoic acid
  4. p-Bromobenzenesulfonic acid

How would you synthesize the following substances starting from benzene or phenol? Assume that ortho- and para-substitution products can

be separated.

(a)o-Bromobenzoic acid (b)p-Methoxytoluene

(c)2,4,6-Trinitrobenzoic acid (d)m-Bromoaniline

Question: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.

Draw resonance structures of the intermediate carbocations in the bromination of naphthalene, and account for the fact that naphthalene undergoes electrophilic substitution at C1 rather than C2.

Propose a mechanism to account for the reaction of benzene with 2,2,5,5 tetramethyltetrahydrofuran.
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