Standard difficulty · 20 questions · 40 marks
Show your working for Sections B and C. Answers are on the last page — try every question first!
Amines · AW-12C-AMN-2026-V1 · For parents — fold back or tear off before handing the sheet to your child.
| Q | Answer | Working |
|---|---|---|
| 1 | (d) a lone pair of electrons | — |
| 2 | (a) ethanamine | N-substituents are named with the prefix N- |
| 3 | (c) tertiary (3°) amine | count the carbon groups on nitrogen |
| 4 | (d) no reaction | N,N-dimethylaniline is tertiary (3°) |
| 5 | (a) phenylmethanamine < methanamine < N-methylmethanamine | pKb: N-methylmethanamine 3.27, phenylmethanamine 4.7, methanamine 3.38 (lower pKb, stronger base) |
| 6 | (b) chlorobenzene | — |
| 7 | (c) phenylmethanamine | Hoffmann bromamide degradation: the amine has one carbon fewer than the amide |
| 8 | (c) A is true, but R is false. | A is true: it is a primary (1°) amine. R is false. |
| 9 | Alkyl groups release electrons (+I effect), raising the electron density on nitrogen, so the lone pair is more available to accept a proton. | — |
| 10 | N,N-diethylethanamine; tertiary (3°); no reaction | Hinsberg: 1° soluble in alkali, 2° insoluble, 3° no reaction |
| 11 | benzenamine < phenylmethanamine < N-methylmethanamine | pKb: phenylmethanamine 4.7, benzenamine 9.38, N-methylmethanamine 3.27; aryl amines are weak because the lone pair is spread into the ring |
| 12 | benzene; reduction | the N2+ group is replaced or the ion couples |
| 13 | hexan-1-amine; 90.9 g | RCONH2 + Br2 + 4NaOH → RNH2 + Na2CO3 + 2NaBr + 2H2O; M(amine) = 101 |
| 14 | Hinsberg's reagent: phenylmethanamine gives a sulphonamide that dissolves in alkali; N-methylmethanamine gives a sulphonamide that does not dissolve in alkali. Also, only the primary amine (phenylmethanamine) gives the carbylamine test | Hinsberg separates 1°, 2° and 3° amines |
| 15 | diazotise, then H3PO2 | — |
| 16 | a yellow oily N-nitrosoamine forms | the products depend on the class and on whether the amine is aromatic |
| 17 | Reduction of nitro compounds: C6H5NO2 + 6[H] (Sn/HCl) → C6H5NH2 + 2H2O. Ammonolysis of alkyl halides gives a mixture of 1°, 2° and 3° amines and the quaternary salt. Reduction of nitriles (LiAlH4 or H2/Ni) and of amides (LiAlH4). Gabriel synthesis gives pure primary aliphatic amines. Hoffmann bromamide degradation gives a primary amine with one carbon fewer. | — |
| 18 | A = aniline, B = 2,4,6-tribromoaniline | follow each reagent in turn |
| 19 | benzenamine < N-methylaniline < phenylmethanamine < N-ethylethanamine | alkyl groups (+I) raise basicity, but in water solvation and crowding make the order of methyl amines 2° > 1° > 3°; in aryl amines the lone pair is delocalised into the ring, so they are much weaker. pKb: phenylmethanamine 4.7, benzenamine 9.38, N-methylaniline 9.3, N-ethylethanamine 3 |
| 20 | CH3(CH2)4CONH2 + Br2 + 4NaOH → CH3(CH2)4NH2 + Na2CO3 + 2NaBr + 2H2O; pentan-1-amine; 34.8 g; the reaction removes the carbonyl carbon and always leaves an –NH2 group, so only primary amines form | mol = 0.5 |