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- Answer BOTH parts of this question. (a) Briefly explain the origin of amine basicity. Using resonance structures explain why aniline is a weaker base than methylamine. (b) Draw the structure of compound X and provide a curly arrow mechanism for the reduction in Scheme 1. X 1. NaBH4 2. H₂O Scheme 1 OHGive reasons :(a) Aniline is a weaker base than cyclohexyl amine.(b) It is difficult to prepare pure amines by ammonolysis of alkyl halides.How would you account for the following :(a) Electrophilic susbstitution in case of aromatic amines takes place more readily than benzene.(b) Ethanamide is a weaker base than ethanamine.
- (b) Suggest a reasonable biosynthesis for the naturally occurring alkaloid coniine (isolated from hemlock), starting from octanoic acid. Coniine(a) Although phenoxide ion has more number of resonating structures than carboxylate ion, carboxylic acid is a stronger acid than phenol. Give two reasons.(b) How will you bring about the following converstions?(i) Propanone to propane (ii) Benzoyl chloride to benzaldehyde(iii) Ethanal to but-2-enal(a) Explain why an alkylamine is more basic than ammonia?(b) How would you convert(i) Aniline to nitrobenzene (ii) Aniline to iodobenzene
- 1. (a) Compound A,B and C are isomers with molecular formula of C4H8O. When compound A,B and C reacts with 2,4-dinirophenylhydrazine, a yellow precipitate is formed. Compound B and C show a positive result with silver nitrate in aqueous ammonia. (i) Deduce the structures of A,B and C. (ii) Give the observation when A and B reacts with silver nitrate in aqueous ammonia.Give reasons for the following:(i) Aniline does not undergo Friedal-Crafts reaction.(ii) (CH3)2 NH is more basic than (CH3)3 N in an aqueous solution.(iii) Primary amines have higher boiling point than tertiary amines.(a) Give chemical tests to distinguish between the following pairs of compounds :(i) Pentan-2-ol and Pentan-3-ol (ii) Methanol and Phenol(b) o-nitro phenol is more acidic than o-methoxy phenol. Explain why.
- - Rank the following substances in order of increasing acidity: (a) Phenol, p-methylphenol, p-(trifluoromethyl)phenol (b) Benzyl alcohol, phenol, p-hydroxybenzoic acidAccount for the following :(i) Primary amines (R-NH2) have higher boiling point than tertiary amines (R3N).(ii) Aniline does not undergo Friedel – Crafts reaction.(iii) (CH3)2NH is more basic than (CH3)3N in an aqueous solution.Show how you can synthesize the following compounds starting with benzene, toluene, and alcohols containing no morethan four carbon atoms as your organic starting materials. Assume that para is the major product (and separable fromortho) in ortho, para mixtures.(a) pentan-1-amine (b) N-methylbutan-1-amine