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Chapter 18: Q100P (page 922)

What is the product of the following reaction?

Short Answer

Expert verified

The same mechanism does Friedal-craft acylation using the anhydride as an acid chloride, except the nature of the leaving group differs.

Friedal-craft acylation can be done usinganhydride as they have a resonance stable leaving group they can do all the reactions which can be done by acid chloride.

Step by step solution

01

Friedal-craft acylation

The same mechanism does Friedal-craft acylation using the anhydride as an acid chloride, except the nature of the leaving group differs.

Friedal-craft acylation can be done usinganhydride as they have a resonance stable leaving group they can do all the reactions which can be done by acid chloride.

02

Product of given reaction

The reaction of Toluene with phthalic anhydride in the presence of Lewis acid undergoes friedal craft acylation, in which the pie bond present in the toluene ring act as the nucleophile and gets attached to the electrophile carbonyl carbon of phthalic anhydride and finally of hydrolysis form the product 2-(2-methyl benzoyl) benzoic acid shown as follows:

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Most popular questions from this chapter

Why isn鈥檛 FeBr3 used as a catalyst in the first step of the synthesis of 1,3,5-tribromobenzene?

Use the four compounds shown below to answer the following questions:

  1. Why are the ortho-halo-substituted benzoic acids stronger acids than benzoic acid?
  2. Why is o-fluorobenzoic acid the weakest of the ortho-halo-substituted benzoic acids?
  3. Why do o-chlorobenzoic acid and o-bromobenzoic acid have similar pKa values?

Question: The pKa values of a few ortho-, meta-, and para-substituted benzoic acids are shown below:

The relative pKa values depend on the substituent. For chloro-substituted benzoic acids, the ortho isomer is the most acidic and the para isomer is the least

acidic; for nitro-substituted benzoic acids, the ortho isomer is the most acidic and the meta isomer is the least acidic; and for amino-substituted benzoic acids, the meta isomer is the most acidic and the ortho isomer is the least acidic. Explain these relative acidities.

a. Cl: ortho > meta > para

b. NO2: ortho > para > meta

c. NH2: meta > para > ortho

a. Rank the following esters from most reactive to least reactive in the first slow step of a nucleophilic acyl substitution reaction (formation of the tetrahedral intermediate):

b. Rank the same esters from most reactive to least reactive in the second slow step of a nucleophilic acyl substitution reaction (collapse of the tetrahedral intermediate).

Question: Why does hydration inactivates FeBr3 ?
See all solutions

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