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Chapter 18: Q51P (page 915)

Draw the product of each of the following reactions:

a.

b.

Short Answer

Expert verified

The product of each reactionsare,

a.

b.

Step by step solution

01

Step-by-Step SolutionStep 1: Intramolecular Friedel-Crafts alkylation

In Intramolecular Friedel-Crafts alkylation, the aromatic ring acts as a nucleophile, and the alkyl chloride acts as an electrophile.With the Lewis acid catalyst (AlCl3), C-C bonds are formed, and C-H and C-Cl bonds are broken. The ring formation takes place in these types of reactions.

02

The product formed in reaction (a)

(a) This reaction is intramolecular Friedel-Crafts alkylation, and a carbocation rearrangement occurs in this reaction.

The product formed in intramolecular Friedel-Crafts alkylation (a)

03

Step 3: The product formed in reaction (b)

(b)This reaction is an example of double Friedel-Crafts alkylation, and in this reaction a cyclohexane ring is formed.


The product formed in double Friedel-Crafts alkylation (b)

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Most popular questions from this chapter

A chemist isolated an aromatic compound with molecular formula C6H4Br2. He treated this compound with nitric acid and sulfuric acid and isolated three different isomers, in different amounts, with molecular formula C6H3Br2NO2. What was the structure of the original compound?

A mixture of 0.10 mol benzene and 0.10 mol p-xylene was allowed to react with 0.10 mol nitronium ion until all the nitronium ion was gone. Two products were obtained: 0.002 mol of one and 0.098 mol of the other.

  1. What was the major product?
  2. Why was more of one product obtained than of the other?

Draw the structure of the activated benzene ring and the diazonium ion used in the synthesis of each of the following compounds, whose structures can be found on page 607.

a. butter yellow

b. methyl orange

For each horizontal row of substituted benzenes, indicate

  1. the one that is the most reactive in an electrophilic aromatic substitution reaction.
  2. the one that is the least reactive in an electrophilic aromatic substitution reaction.
  3. the one that yields the highest percentage of meta product in an electrophilic aromatic substitution reaction

1.

2.

3.

Explain why hydroxide ion catalyzes the reaction of piperidine with 2,4-dinitroanisole but has no effect on the reaction of piperidine with 1-chloro-2,4-dinitrobenzene.
See all solutions

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