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Chapter 16: Q6 P (page 493)

What is the major monosubstitution product from the Friedel–Crafts reaction of benzene with 1-chloro-2-methylpropane in the presence of AlCl3 ?

Short Answer

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Alkylation reactions constitute a useful electrophilic aromatic substitution reaction. The reaction involves the introduction of an alkyl group into the benzene ring. The reagents used for this reaction are an alkyl chloride in the presence of .

Step by step solution

01

Friedel-Crafts reaction

Alkylation reactions constitute a useful electrophilic aromatic substitution reaction. The reaction involves the introduction of an alkyl group into the benzene ring. The reagents used for this reaction are an alkyl chloride in the presence of .

02

Major monosubstitution product from the Friedelcraft’s reaction of benzene with 1-chloro-2-methylpropane

The electrophile involved when 1-chloro-2-methylpropane is used in Friedal-Crafts reaction is 1-chloro-2-methylpropyl carbocation. It is primary and will rearrange to form a more stable tert-butyl carbocation. This carbocation attacks the benzene ring to form tert-butyl benzene as the product. The reaction can be given as:

Friedelcraft’s reaction of benzene with 1-chloro-2-methylpropane

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Most popular questions from this chapter

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.

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

Question: How would you synthesize the following compounds from benzene? Assume that ortho and para isomers can be separated.

a)

b)

Question: How might you synthesize the following substances from benzene?

(a) m-Chloronitrobenzene

(b) m-Chloroethylbenzene

(c) 4-Chloro-1-nitro-2-propylbenzene

(d) 3-Bromo-2-methylbenzenesulfonic acid

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
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