Quiz - Chemistry Benzene Substituents | Chemistry of Benzene Substituents

1

Which of the following types of reactions corresponds to the reaction between toluene and Br2 under photolytic conditions?

Electrophilic addition

Electrophilic substitution

Radical addition

Radical substitution

Radical process via an initiation step to activate Br2 then propagation steps. A hydrogen atom is substituted by a bromine

2

Which of the following statements about the reactivity of toluene is correct?

Oxidation of toluene with aqueous KMnO4 gives benzoic acid

Reaction of toluene with Br2 in the presence of FeBr3 gives 2- and 4-bromotoluene

The methyl substituent is relatively acidic (pKa ~ 41) and can be deprotonated with a strong base

All of the above

3

Which of the following types of reactions corresponds to the reaction between bromobenzene and NaNH/ NH3?

Nucleophilic aromatic substitution

Electrophilic aromatic substitution

Addition-elimination

Radical substitution

Nucleophilic aromatic substitution through benzyne intermediate:

4

Which of the following statements about phenol is correct?

PhOH behaves as a typical alcohol

PhOH reacts with NaOH to give sodium phenoxide

A keto-enol equilibrium exists with PhOH and the keto form is favored

All of the above

There is a keto-enol equilibrium with phenol but the enol form is favored by aromaticity. The proton of the hydroxy function is acidic because the corresponding anion is stabilized by resonance. NaOH reacts with phenol to give sodium phenoxide

5

Which of the following statements about aniline is incorrect?

Aniline is a primary amine

Reaction of PhNH2 with MeCOCl gives the amide PhNHCOMe

Treatment of PhNH2 with NaNO2 and aqueous HCl gives the diazonium cation PhN2+

None of the above

6

Which of the following statements about the diazonium cation PhN2+ is correct?

Coupling of PhN2+ with phenol occurs with loss of N2

During the Sandmeyer reaction, PhN2+ reacts with NaCN to give cyanobenzene

PhN2+ is hydrolysed in water to phenol

All of the above

Hydrolysis of arenediazonium salts: