Chapter 18: 18-17P (page 677)

Label each compound as more or less reactive than benzene in electrophilic aromatic substitution.

Short Answer

Expert verified

a. More reactive

b. More reactive

c. Less reactive

d. Less reactive

Step by step solution

Electrophilic aromatic substitution reaction

The electrophilic aromatic substitution reaction involves the substitution of an electrophile on the aromatic rings. The reactivity towards electrophilic-substitution depends upon the substituents on the aromatic compound.

Reactivity towards electrophilic aromatic substitution reaction

The electron-withdrawing substituents on the aromatic ring decrease the rate of the substitution or the compound is less reactive.

The electron-donating substituents on the aromatic ring increase the rate of the substitution reaction or the compound is more reactive.

Explanation

a. The alkyl group on the benzene is an electron-donating substituent; therefore, the compound is more reactive.

b. The OH group on the benzene is an electron-donating substituent; therefore, the compound is more reactive.

c. The\({\rm{COOC}}{{\rm{H}}_{\rm{2}}}{\rm{C}}{{\rm{H}}_{\rm{3}}}\)group on the benzene is an electron-withdrawing substituent; therefore, the compound is less reactive.

d. The \(\mathop {\rm{N}}\limits^{\rm{ + }} {\left( {{\rm{C}}{{\rm{H}}_{\rm{3}}}} \right)_{\rm{3}}}\) group on the benzene is an electron-withdrawing substituent; therefore, the compound is less reactive.