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NCERT Exemplar · Q66

Q.Which of the following reactions is/are correct? (Two or more options may be correct.)

(i) CH3Cl + 2 NH3 → CH3NH2 + NH4Cl;
(ii) (CH3)3C–Cl + aqueous KOH → 2-methylprop-1-ene, (CH3)2C=CH2;
(iii) cyclohexyl chloride + alcoholic KOH → cyclohexene;
(iv) a primary aliphatic amine, (CH3)2CHCH2NH2 (isobutylamine), + HNO2 at 0 °C → the corresponding alcohol.
(i) reaction
(i)
(ii) reaction
(ii)
(iii) reaction
(iii)
(iv) reaction (iv)
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Three of the four reactions are written correctly. Only (ii) is wrong: aqueous KOH on a tertiary halide gives mainly substitution (the alcohol), whereas the drawn product is an alkene, which requires alcoholic KOH.

Reaction (i) — correct

CH3Cl + 2 NH3 → CH3NH2 + NH4Cl. Ammonia acts as a nucleophile (ammonolysis of an alkyl halide); the second molecule of NH3 neutralises the HCl formed. Correct.

Reaction (ii) — incorrect

(CH3)3C–Cl (a tertiary halide) with AQUEOUS KOH undergoes mainly nucleophilic substitution (SN1) to give tert-butyl alcohol, (CH3)3C–OH. Elimination to 2-methylprop-1-ene is favoured by ALCOHOLIC KOH (a stronger, less solvated base). As written (aqueous KOH → alkene), the reaction is not correct.

Reaction (iii) — correct

Cyclohexyl chloride + alcoholic KOH → cyclohexene + KCl + H2O. Alcoholic KOH promotes dehydrohalogenation (E2 elimination). Correct.

Reaction (iv) — correct …

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