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Chapter 18: Q 57. (page 724)

Question: Friedel-Crafts alkylation of benzene with (R)-2-chlorobutane and AlCl3 affords sec-butylbenzene.

  1. How many stereogenic centers are present in the product?
  2. Would you expect the product to exhibit optical activity? Explain, with reference to the mechanism.

Short Answer

Expert verified

b. The reaction of the carbocation with the benzene results in the formation of a racemic mixture of two products which are optically inactive in nature as shown below:

Step by step solution

01

Friedel-crafts alkylation

In this reaction, benzene is treated with an alkyl halide and a Lewis acid such as AlCl3 to result in the formation of alkyl benzene. This reaction is used to transfer an alkyl group from one molecule to another.

In this reaction, the electrophile is generated. The Lewis acid reacts with the alkyl halide and results in the formation of the acid-base complex. The reaction with the primary alkyl halides generates the electrophile in the form of the acid-base complex.

For the secondary and tertiary alkyl halides, the electrophile is generated in the form of carbocation.

02

Number of stereogenic centers present in the given molecule

The reaction of benzene with the (R)-2-chlorobutane and AlCl3produces the following product:

  1. The product of the given reaction consists only of the stereogenic center as shown in the following structure:

The mechanism for the given Friedel-crafts alkylation with the secondary alkyl halide (R)-2-chlorobutane involves the formation of the acid-base complex in the first step as shown in the following structure

In the next step, the formation of the trigonal planar carbocation takes place as shown below. The carbocation is achiral in nature and it can react with benzene from both above and below the plane of the molecule:

The reaction of the carbocation with the benzene results in the formation of a racemic mixture of two products which are optically inactive in nature as shown below:

A racemic mixture of two products will be formed which are optically inactive.

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Most popular questions from this chapter

Question: Synthesize each compound from toluene and any other organic or inorganic reagents.

Question: Rank the aryl halides in each group in order of increasing reactivity in nucleophilic aromatic substitution by an addition鈥揺limination mechanism.

  1. chlorobenzene, p-fluoronitrobenzene, m-fluoronitrobenzene
  2. 1-fluoro-2,4-dinitrobenzene, 1-fluoro-3,5-dinitrobenzene, 1-fluoro-3,4-dinitrobenzene
  3. 1-fluoro-2,4-dinitrobenzene, 4-chloro-3-nitrotoluene, 4-fluoro-3-nitrotoluene

Question: Explain the following observation. Ethyl 3-phenylpropanoate (C6H5CH2CH2CO2CH2CH3) reacts with electrophiles to afford ortho- and para-disubstituted arenes, but ethyl 3-phenylprop-2-enoate (C6H5=CHCO2CH2CH3) reacts with electrophiles to afford meta-disubstituted arenes.

Question: Draw a stepwise mechanism for the following reaction, which results in the synthesis of bisphenol F (R = H), an additive used in a variety of packaging materials. Bisphenol F is related to BPA (bisphenol A, R = ), a reagent used to harden some plastics, now removed from certain baby products because of its estrogen-like activity that can disrupt endocrine pathways.

For each of the following substituted benzenes: (1) \({{\bf{C}}_{\bf{6}}}{{\bf{H}}_{\bf{5}}}{\bf{Br}}\); (2) \({{\bf{C}}_{\bf{6}}}{{\bf{H}}_{\bf{5}}}{\bf{CN}}\) ; (3) \({{\bf{C}}_{\bf{6}}}{{\bf{H}}_{\bf{5}}}{\bf{OCOC}}{{\bf{H}}_{\bf{3}}}\):

  1. Does the substituent donate or withdraw electron density by an inductive effect?
  2. Does the substituent donate or withdraw electron density by a resonance effect?
  3. On balance, does the substituent make a benzene ring more or less electron-rich than benzene itself?
  4. Does the substituent activate or deactivate the benzene ring in electrophilic aromatic substitution?
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