Question

Draw the product(s) of each of the following reactions:

1. benzoic acid + HNO₃/H₂SO₄
2. isopropylbenzene + Cl₂ + FeCl₃
3. p-xylene + acetyl chloride + AlCl₃ followed by H₂O
4. o-methylaniline + benzenediazonium chloride
5. cyclohexyl phenyl ether + Br₂
6. phenol + H₂SO₄ + Δ
7. ethylbenzene + Br₂/FeBr₃
8. m-xylene + Na₂Cr₂O₇ + HCl + Δ

Short answer

The products of the reactions are given below:

a)

b)

c)

d)

e)

f)

g)

h)

Step-by-step solution

(a) Nitration

The catalyst used sulfuric acid, generate electrophile from nitric acid. Sulfuric acid releases one proton and HNO₃ gets protonated and then loses water gives electrophile ‘nitronium ion’.

Thus, nitration of benzene ring is an example of aromatic electrophilic substitution.

(b) Halogenation of benzene

Chlorination of benzene ring involves addition of chlorine electrophile using the Lewis acid catalyst ferric chloride.Then the base FeCl₄ abstract proton from hydrogen ring gives the halogenated benzene.

(c) Friedel-crafts acylation reaction

The electrophile needed for acylation reaction is generated by the reaction of acyl chloride with AlCl₃.Acylium ion adds to the benzene ring gives the product.

(d) Synthesis of azo benzene

Azo benzene product contains an azo linkage synthesized by the reaction of substituted benzene with benzene diazonium chloride. Azo linkage prefers to occur at less sterically hindered para-position.

(e) Bromination of cyclohexyl phenyl ether

Cyclohexyl phenyl ether brominated to give p-bromo substituted product. Halogenation of benzene ring gives a major product and minor product.

(f) Synthesis of p-oxobenzenesulfonic acid

Phenol reacts with sulfuric acid adds sulphonic acid group to the ortho position gives a substituted benzene product p-oxobenzenesulfonic acid.

(g) Halogenation

Halogenation is an aromatic electrophilic substitution reaction involves the addition of bromine molecule using the Lewis acid catalyst FeBr₃.

(h) Oxidation reaction

m-xylene undergo oxidation reaction in presence of oxidizing agent Na₂Cr₂O₇ gives the desired product. Methyl group oxidized to get acid substituted product.

Thus, all the given reactants give its corresponding products by reaction at different condition.