Question

Draw the products of each reaction.

Short answer

Hydrocarbons that contain one or more benzene-like rings are called aromatic compounds.

All reactions of aromatic compounds are modified versions of electrophilic substitution reactions. This is because the benzene ring is electron-rich.

Monosubstituted and disubstituted benzenes also undergo electrophilic substitution and the product formed depends on the substituents.

Step-by-step solution

Reactions of aromatic compounds

Hydrocarbons that contain one or more benzene-like rings are called aromatic compounds.

All reactions of aromatic compounds are modified versions of electrophilic substitution reactions. This is because the benzene ring is electron-rich.

Monosubstituted and disubstituted benzenes also undergo electrophilic substitution and the product formed depends on the substituents.

Ortho-para and meta directing groups

When electrophilic substitution is carried out in substituted benzene, the ortho, para, and meta products are formed in different proportions.

This is because of resonance in the substituted benzene.

If the resonance makes ortho and para positions electron-rich, ortho-para substitution predominates meta substitution and forms the major proportion of the product. They are called activating groups.

If resonance makes the ortho-para positions electron-deficient, electrophilic substitution produces meta products. They are called deactivating groups.

Products of given reactions

a. The compound contains a hydroxyl group which is an activating group and a nitro group which is a deactivating group.

Therefore, substitution occurs at the position ortho and para to the hydroxyl group.

b. The compound contains an acetoxy group which is an activating group and a chloride group which is a deactivating group.

Therefore, substitution occurs at the position ortho to the acetoxy group.

c. The compound contains a methyl group which is an activating group and carbonyl which is a deactivating group.

Therefore, substitution occurs at the position ortho and para to the methyl group.

d. The compound contains a methoxy group which is a strong activating group and methyl acetate group which is a moderate deactivating group.

Therefore, substitution occurs at the position ortho to the methoxy group.

e. The compound contains a methoxy group which is an activating group and bromide which is a deactivating group.

Therefore, substitution occurs at the position ortho and para to the methoxy group.

f. The compound contains a nitro group which is an activating group and fluoride which is a deactivating group.

The alkyl sulfide substituted fluorine at the ortho position.