Q.How many moles of methylbromide are required to convert ethanamine to N, N-dimethyl ethanamine ?
Concept understanding — Chemical Reactions of Amines
ALKYLATION: successive reaction with R-X climbs 1 to 2 to 3 degree amine to quaternary ammonium salt. ACYLATION: primary/secondary amines + acetyl chloride or acetic anhydride (pyridine present) give an N-alkyl acetamide; aniline + benzoyl chloride/NaOH giving N-phenylbenzamide is specifically the SCHOTTEN-BAUMANN REACTION. REACTION WITH NITROUS ACID (NaNO2 + HCl, in situ) distinguishes all three amine classes AND aliphatic from aromatic: primary ALIPHATIC amines give an unstable alkyl diazonium salt that instantly loses N2 to the alcohol; primary AROMATIC amines at 273-278 K give a diazonium salt that is reasonably stable short-term (this specific step is DIAZOTISATION, feeding the next unit's diazonium-salt chemistry); SECONDARY amines give a yellow, water-insoluble N-nitrosoamine oil (LIEBERMANN'S NITROSO TEST); TERTIARY aliphatic amines give a soluble trialkylammonium nitrite salt, while tertiary AROMATIC amines react at the ring instead, giving a p-nitroso compound. CARBYLAMINE REACTION and MUSTARD OIL REACTION (separate concepts) both specifically identify primary amines. ELECTROPHILIC SUBSTITUTION IN ANILINE (a separate concept) covers -NH2's activating, ortho/para-directing behaviour on the ring itself.
Section 13.6.2's exhaustive-methylation rule: a primary amine needs 3 moles of methyl halide to reach the quaternary salt, but N,N-dimethylethanamine is only a TERTIARY amine, needing just 2 moles from the starting primary ethanamine.
2 moles of methyl bromide.
Step 1. Identify starting material and target. Ethanamine, CH3-CH2-NH2, is a primary amine. N,N-Dimethylethanamine, CH3-CH2-N(CH3)2, is a TERTIARY amine (three groups -- ethyl, methyl, methyl -- on nitrogen), NOT the fully quaternary salt.
Step 2. Apply section 13.6.2's stepwise alkylation. Each mole of methyl bromide reacted replaces one more N-H hydrogen with a methyl group: ethanamine (primary, two N-H) + one mole CH3Br gives N-methylethanamine (secondary, one N-H remaining) + HBr; N-methylethanamine + a SECOND mole of CH3Br gives N,N-dimethylethanamine (tertiary, no N-H remaining) + HBr.
Step 3. Count the moles used. Two successive methylation steps, each consuming one mole of methyl bromide, are needed to go from the primary amine all the way to this specific tertiary product -- a third mole would push the reaction on to the quaternary ammonium salt instead, which is NOT what is being asked for here.
2 moles of methyl bromide.
Applying section 13.6.2's one-mole-per-methylation-step rule, recognising the target (N,N-dimethylethanamine) is a tertiary amine reached after exactly two methylation steps from the primary starting amine
- Assuming three moles are needed (the number stated in section 13.6.2 for converting a PRIMARY amine all the way to the QUATERNARY salt), without checking that the actual target here, N,N-dimethylethanamine, is only a tertiary amine, one methylation step short of the quaternary salt.
- Confusing the target compound's own name (which already tells you it has two N-methyl groups) with the number of NEW methyl groups that must be added starting from ethanamine, which has zero methyl groups on nitrogen to begin with.
- CBSE 2025Set ANNUAL1 markMCQQ.The compound that reacts with nitrous acid to give yellow oily liquid is ________.(a) N-methylaniline(b) Nitro benzene(c) N,N-dimethyl aniline(d) Aniline
›Reveal solutionSolution
Nitrous acid reacts differently with the three classes of aromatic amines; only the secondary amine, N-methylaniline, gives the diagnostic yellow oily liquid (an N-nitrosamine) — this is a classic distinguishing test for 1°, 2°, and 3° amines.
Reaction of amines with HNO2 (generated in situ from NaNO2+HCl, at 0–5°C):
- Primary aromatic amine (aniline, option d): forms a benzenediazonium chloride, C6H5N2+Cl−, a colourless/pale-yellow crystalline solid in cold solution — not an oily liquid.
- Secondary aromatic amine (N-methylaniline, option a): the N-H hydrogen is replaced by the nitroso group (−N=O), giving N-methyl-N-nitrosoaniline, C6H5N(CH3)−N=O — this N-nitrosamine is a characteristic yellow oily liquid.
- Tertiary aromatic amine (N,N-dimethylaniline, option c): since there is no N-H to substitute, nitrosation occurs on the aromatic ring instead (at the position para to the strongly activating −N(CH3)2 group), giving p-nitroso-N,N-dimethylaniline, which separates as a green crystalline solid.
- Nitrobenzene (option b) does not react with nitrous acid at all under these conditions (the −NO2 group is already fully oxidised and unreactive here).
So the compound that gives the yellow oily liquid on treatment with nitrous acid is the secondary amine, N-methylaniline.
✓Final answerThe correct answer is (a) N-methylaniline — its secondary −NH− group is nitrosated to give the yellow oily N-nitrosamine, C6H5N(CH3)NO.
- CBSE 2024Set ANNUAL1 markMCQQ.When aniline reacts with acetic anhydride, the product formed is :(a) p-aminoacetophenone(b) o-aminoacetophenone(c) acetanilide(d) m-aminoacetophenone
›Reveal solutionSolution
Aniline undergoes N-acylation with acetic anhydride: the amine nitrogen's lone pair attacks the anhydride's carbonyl carbon, displacing acetate, to give the amide acetanilide.
Aniline, C6H5NH2, has a nucleophilic nitrogen lone pair that attacks the electrophilic carbonyl carbon of acetic anhydride, (CH3CO)2O, in a nucleophilic acyl substitution reaction. One acetyl group is transferred to nitrogen (displacing acetate/acetic acid as the leaving group), converting the -NH2 into an amide -NHCOCH3 group: C6H5NH2+(CH3CO)2O→C6H5NHCOCH3 (acetanilide)+CH3COOH The product, N-phenylacetamide, is commonly called acetanilide, and this specific N-acetylation reaction is also used industrially/in the lab to protect (and mildly deactivate) the -NH2 group before performing further electrophilic aromatic substitutions on the ring. The other options (p-/o-/m-aminoacetophenone) describe ring-substituted ketones, which would require a Friedel-Crafts acylation on a different substrate, not the simple N-acylation of aniline's amino group.
✓Final answerThe correct answer is (c) acetanilide — aniline's -NH2 group is acetylated by acetic anhydride to give the amide, acetanilide.
- CBSE 2022Set ANNUAL1 markMCQQ.Acid anhydride on reaction with primary amine gives compound having a functional group _____.(a) amide(b) nitrile(c) secondary amine(d) imine
›Reveal solutionSolution
Acylation of a primary amine by an acid anhydride produces an amide.
An acid anhydride reacts with a primary amine by nucleophilic acyl substitution: the amine's lone pair attacks the carbonyl carbon of the anhydride, displacing a carboxylate/carboxylic acid and forming an N-substituted amide:
RNH2+(CH3CO)2O→RNHCOCH3 (amide)+CH3COOH
The functional group produced is therefore the amide group, –CONH–.
✓Final answer(a) amide
- CBSE 2020Set ANNUAL1 markMCQQ.The number of moles of methyl iodide required to prepare tetramethyl ammonium iodide from 1 mole of methyl amine is/are:(a) 1(b) 2(c) 3(d) 4
›Reveal solutionSolution
Converting a primary amine to a quaternary ammonium salt by exhaustive methylation consumes 3 moles of CH₃I per mole of amine.
Methylamine, CH3NH2, has one methyl group and two N–H bonds. Exhaustive (excess) alkylation with methyl iodide replaces both remaining N–H hydrogens and then alkylates the resulting tertiary amine's lone pair to form the quaternary ammonium salt:
CH3NH2CH3I(CH3)2NHCH3I(CH3)3NCH3I(CH3)4N+I−
Three successive methylations (three moles of CH3I) are required to go from CH3NH2 to (CH3)4N+I− (tetramethylammonium iodide).
✓Final answer(c) 3
- CBSE 2018Set ANNUAL1 markMCQQ.Oxidation of aniline with acidified potassium dichromate gives :(a) benzaldehyde(b) p-benzo quinone(c) benzyl alcohol(d) benzoic acid
›Reveal solutionSolution
Vigorous oxidation of aniline with acidified potassium dichromate (K2Cr2O7/H+) oxidises the ring, converting aniline into p-benzoquinone.
Aniline's strongly activating −NH2 group makes the ring very susceptible to oxidative attack. Acidified dichromate (a strong oxidising agent) oxidises aniline not at a side chain (there is none) but at the ring itself, removing the amino nitrogen as part of the process and installing two carbonyl groups at the para positions to give p-benzoquinone (C6H4O2). Benzaldehyde (a) and benzoic acid (d) would arise from oxidation of a methyl/aldehyde side chain (as in toluene or benzyl alcohol oxidation), which aniline does not have. Benzyl alcohol (c) is unrelated — it is not a plausible oxidation product of aniline at all.
✓Final answerb) p-benzoquinone — acidified K2Cr2O7 oxidises aniline's ring to give p-benzoquinone.
- CBSE 2017Set ANNUAL1 markMCQQ.When primary amine reacts with CHCl3 in alcoholic KOH, the product is _______.(a) aldehyde(b) alcohol(c) cyanide(d) an isocyanide
›Reveal solutionSolution
Primary amine + CHCl3/alcoholic KOH is the carbylamine reaction, giving a foul-smelling isocyanide.
This is the carbylamine (isocyanide) test, characteristic of primary amines only (both aliphatic and aromatic): the amine, chloroform and alcoholic KOH react to form an isocyanide (carbylamine) with a distinctive foul/offensive smell, along with KCl and water:
RNH2+CHCl3+3KOH→RNC+3KCl+3H2O
Secondary and tertiary amines do not give this test, which is why it is used to distinguish primary amines from the other two classes.
✓Final answer(d) an isocyanide (carbylamine reaction).
- CBSE 2016Set ANNUAL1 markMCQQ.Which of the following amines yield foul smelling product with haloform and alcoholic KOH?(a) Ethylamine(b) Diethylamine(c) Triethylamine(d) Ethylmethylamine
›Reveal solutionSolution
The carbylamine reaction (foul-smelling isocyanide) is given only by primary amines.
When a primary amine reacts with chloroform (CHCl3) in the presence of alcoholic KOH, it forms an isocyanide (carbylamine), which has an extremely unpleasant, foul odour — this is the carbylamine test, specific to primary amines only (both aliphatic and aromatic).
RNH2+CHCl3+3KOH→RNC+3KCl+3H2O
Among the given options, ethylamine (C2H5NH2) is the only primary amine; diethylamine and ethylmethylamine are secondary amines, and triethylamine is a tertiary amine — none of these give the carbylamine reaction (they lack the required N-H needed for isocyanide formation in this test).
✓Final answer(a) Ethylamine.
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