Describe simple chemical tests that would distinguish between: (a) benzene and toluene; (b) bromobenzene and bromocyclohexane; (c) bromobenzene and 3 -bromo-1-hexene: (d) ethylbenzene and benzyl alcohol \(\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{OH}\right)\).

Short Answer

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(a) Benzene and toluene can be distinguished using oxidation test with potassium permanganate (\(KMnO_4\)) in alkaline medium. Benzene shows no reaction, while toluene oxidizes to benzoic acid. (b) Bromobenzene and bromocyclohexane can be distinguished using sodium metal substitution reaction. Bromocyclohexane reacts to give a cyclohexene smell, while bromobenzene doesn't. (c) Bromobenzene and 3-bromo-1-hexene can be distinguished using Baeyer’s test with dilute alkaline potassium permanganate solution. Bromobenzene shows no reaction, whereas 3-bromo-1-hexene decolorizes the solution due to the presence of a carbon-carbon double bond. (d) Ethylbenzene and benzyl alcohol can be distinguished using Lucas test with \(ZnCl_2\) and concentrated HCl. Benzyl alcohol turns white turbid due to benzyl chloride formation, while ethylbenzene does not react.

Step by step solution

01

(a) Distinguishing between benzene and toluene

Benzene and toluene can be distinguished using the oxidation test. The reagent used in this test is potassium permanganate (\(KMnO_4\)) in an alkaline medium. Benzene upon oxidation with \(KMnO_4\) does not give any reaction due to the absence of alkyl group. On the other hand, toluene oxidises to benzoic acid. So, this reaction can be used to distinguish between benzene and toluene.
02

(b) Distinguishing between bromobenzene and bromocyclohexane

Bromobenzene and bromocyclohexane can be distinguished using a substitution reaction involving sodium (Na). When bromocyclohexane is heated with sodium metal, a characteristic smell of cyclohexene is observed due to the formation of cyclohexene. Bromobenzene, however, does not undergo this reaction. So, this reaction can be used to distinguish between bromobenzene and bromocyclohexane.
03

(c) Distinguishing between bromobenzene and 3-bromo-1-hexene

Bromobenzene and 3-bromo-1-hexene can be distinguished using the Baeyer’s test. The reagent used in this test is a dilute alkaline potassium permanganate solution. Bromobenzene does not react because it does not have a carbon-carbon double bond, while 3-bromo-1-hexene decolorizes the purple colour of the solution due to the presence of a carbon-carbon double bond. So, Baeyer’s test can be used to distinguish between bromobenzene and 3-bromo-1-hexene.
04

(d) Distinguishing between ethylbenzene and benzyl alcohol

We can distinguish between ethylbenzene and benzyl alcohol using Lucas test. The reagent used in this test is Lucas' reagent, which is a mixture of zinc chloride (\(ZnCl_2\)) and concentrated hydrochloric acid (HCl). Benzyl alcohol quickly turns white turbid due to the formation of benzyl chloride, ethylbenzene, however, does not react. So, the Lucas test can be used to distinguish between ethylbenzene and benzyl alcohol.

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