The chapter “Amines” is crucial because it links fundamental concepts of structure, basicity, and reaction mechanisms with high-scoring board and competitive exam problems. Questions from this chapter commonly test how pK values relate, how substituents and resonance/inductive/steric effects control basicity and orientation in reactions, and how amines behave under diazotization conditions. Strong mastery here improves accuracy in both numerical and reasoning-based MCQs.
20
Minutes
15
Questions
1 / -0
Marking
Q1. A 1.0 L aqueous solution contains methylamine (). To this solution of HCl is added. Given , calculate the pH of the resulting solution (assume volumes additive and neglect activity coefficients).
Q2. Arrange the following amines in order of decreasing basicity in aqueous solution: (i) (n‑propylamine), (ii) (aniline), (iii) (diethylamine), (iv) (trimethylamine).
Q3. When aniline () is nitrated using a mixture of concentrated and (without protecting the –NH), which is the major nitro-substituted product formed?
o‑Nitroaniline (‑nitroaniline)
p‑Nitroaniline (‑nitroaniline)
m‑Nitroaniline (‑nitroaniline)
2,4‑Dinitroaniline
Q4. Statement I: N,N‑Dimethylaniline is a weaker base than aniline in aqueous solution at 25°C.
Statement II: This is mainly because steric hindrance from the two methyl groups in N,N‑dimethylaniline reduces solvation/stabilization of its protonated form more than the +I effect of the methyl groups increases intrinsic basicity.
Which of the following is correct?
Both Statement I and Statement II are true, and Statement II correctly explains Statement I.
Both Statement I and Statement II are true, but Statement II does not correctly explain Statement I.
Statement I is true but Statement II is false.
Statement I is false and Statement II is true.
Q5. To synthesize ‑bromoaniline (‑bromoaniline) from aniline () with para‑selectivity, which of the following minimal sequences of steps is most appropriate?
Direct bromination of aniline with (aq) at room temperature.
Acetylate aniline to acetanilide (e.g. with or ), brominate the acetanilide with to give ‑bromoacetanilide, then hydrolyze the amide to obtain ‑bromoaniline.
Acetylate aniline to acetanilide, brominate the acetanilide to give ‑bromoacetanilide, then hydrolyze the amide to obtain ‑bromoaniline.
Protonate aniline to its anilinium salt (HCl) and then brominate with (aq) to obtain ‑bromoaniline.
Q6. If aniline has at , what is the of its conjugate acid ? (Use
.)
Q7. The following reaction sequence is carried out:
What is the major final organic product?
Q8. Arrange the isomeric nitroanilines in order of increasing basicity in aqueous solution:
Q9. Which pair of amines (X, Y) shows that X is more basic than Y in the gas phase but X is less basic than Y in aqueous solution at ?
Q10. Which of the following amines will be converted most readily into the corresponding diazonium salt by treatment with at – (i.e., which forms the diazonium most easily)?
(p-methoxyaniline)
(aniline)
(benzylamine)
(p-nitroaniline)
Q11. A 0.100 M aqueous solution of methylamine () at 25°C has . Using the approximation , estimate the percentage of methylamine present as its protonated form .
0.67%
6.7%
43%
25%
Q12. To prepare p-nitroaniline (---) from benzene with minimum side products, which of the following sequences of steps and reagents is the most appropriate?
Benzene —(HNO_3/H_2SO_4)→ nitrobenzene —(Sn/HCl)→ aniline —(HNO_3/H_2SO_4)→ nitration of aniline (gives mixture)
Benzene —(Cl_2/FeCl_3)→ chlorobenzene —(NH_3, high T, high P)→ aniline —(HNO_3/H_2SO_4)→ nitroaniline
Benzene —(HNO_3/H_2SO_4)→ nitrobenzene —(HNO_3/H_2SO_4)→ dinitrobenzene —(H_2/Pd)→ mixture of aminonitrobenzenes
Benzene —(HNO_3/H_2SO_4)→ nitrobenzene —(Fe/HCl or H_2/Pd)→ aniline —(Ac_2O or CH_3COCl)→ acetanilide —(HNO_3/H_2SO_4)→ p-nitroacetanilide —(H_3O^+)→ p-nitroaniline
Q13. Considering inductive (+I) effects and solvation of protonated species in water, which of the following amines is the most basic in aqueous solution?
(diethylamine)
(triethylamine)
(ethylamine)
(ammonia)
Q14. Arrange the isomeric aminobenzoic acids in order of decreasing basicity (availability of the –NH_2 lone pair for protonation) of the amino group in aqueous solution: 2-aminobenzoic acid (o-), 3-aminobenzoic acid (m-), 4-aminobenzoic acid (p-). Which order is correct?
o- > m- > p-
p- > o- > m-
m- > o- > p-
o- > p- > m-
Q15. A primary aliphatic amine X on treatment with NaNO_2/HCl at 0–5°C followed by warming gives 2-butanol as the major product. Which of the following is X?
(1-aminobutane)
(2-aminobutane)
(tert-butylamine)
(2-methyl-1-propanamine, isobutylamine)