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Chapter 18: 26 P (page 709)

Draw the products of each reaction

a)

b)

c)

Short Answer

Expert verified

a)

b)

c)

Step by step solution

01

Nucleophilic aromatic substitution

The substitution reaction in which the nucleophile displaces a good leaving group such as halide on an aromatic ring is known as nucleophilic aromatic substitution.

These reactions follow the addition-elimination mechanism.

02

Products of the reaction

a) Aryl halides on treatment with a strong base like NaNH2 generate reactive intermediate benzyne.

When NaNH2is used, available nucleophile NH2-reacts with benzyne and gives aniline as the product.

b) Treatment of 1-chloro-4-methoxy with sodium hydroxide in the presence of ammonia, forms a mixture of two products.

c) Treatment of 1-chloro-2-ethylbenzene with potassium amide in the presence of ammonia, forms a mixture of two products.

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Most popular questions from this chapter

Explain why each of the following reactions will not form the given product. Then, design a synthesis of A from benzene and B from phenol C6H5OH.

For each N-substituted benzene, predict whether the compound reacts faster than, slower than, or at a similar rate to benzene in electrophilic aromatic substitution. Then draw the major product (s) formed when each compound reacts with a general electrophile E+.

Which substituents have an electron-withdrawing and which have an electron-donating inductive effect

aCH3CH2CH2CH2-

bBr-

cCH3CH2O-

In Step [2] of Mechanism 18.1, loss of a proton to form the substitution product was drawn using one resonance structure only. Use curved arrows to show how the other two resonance structures can be converted to the substitution product (PhE) by removal of a proton with: B.

Draw the products of each reaction.
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