Class 12 Chemistry Chapter 9 Amines packs around 38 named reactions, 17 pKb data points, and 9 diazonium conversions into NCERT Sections 9.1 to 9.10 - making it the second most reaction-dense Organic block of the year after Chapter 8. This Collegedunia formula sheet collates every preparation route, named reaction, basicity ranking, and diazonium conversion on a printable revision page aligned with the 2026-27 syllabus.

9 pages | 38 reactions | 6 preparation routes · Class 12 Chemistry Chapter 9, 2026-27 NCERT
  • CBSE Weightage: 4 to 6 marks
  • JEE Main Weightage: 2 to 3 percent (2 to 3 questions per paper)
  • NEET Weightage: 1 to 2 questions per year
Chapter 9 Amines Formula Sheet PDF

The compact sheet that follows lists every reaction, basicity trend, and diazonium conversion with its NCERT section reference.

This formula sheet is curated by Collegedunia subject experts, mapped to the 2026-27 new NCERT edition, and refined against the last five years of CBSE Board, JEE Main, and NEET papers.

Also Check:

Amines Formula Sheet - Class 12 Chemistry

Amines Symbol and Notation Glossary for 12th Chemistry

The glossary below locks in every notation used in the master table. More than half of the 1-mark CBSE slips on Chapter 9 come from mis-classifying an amine (counting R groups instead of N-H bonds) or confusing the alkyl diazonium with the aryl diazonium.

SymbolMeaningTypical Unit / Note
R-NH2Primary (1°) amineTwo N-H bonds (e.g. CH3NH2)
R2NH or R-NHR'Secondary (2°) amineOne N-H bond (e.g. (CH3)2NH)
R3NTertiary (3°) amineNo N-H bond (e.g. (CH3)3N)
R4N+X-Quaternary ammonium salte.g. (CH3)4N+I-
Ar-NH2Arylamine-NH2 on sp2 ring C (e.g. aniline)
Ar-N2+X-Arenediazonium saltUsed at 273 to 278 K only (stable below 5°C)
Kb, pKbBase dissociation constant / its -logSmaller pKb = stronger base
+I effectInductive electron donationAlkyl groups raise basicity in gas phase
EASElectrophilic aromatic substitution-NH2: strong o/p-director; -NH3+: m-director
EDG / EWGElectron-donating / withdrawing groupEDG raises Ar-NH2 basicity; EWG lowers it
PhSO2ClBenzenesulphonyl chloride (Hinsberg)Distinguishes 1°/2°/3° amines
H3PO2Hypophosphorous acidReduces Ar-N2+ to Ar-H
Hofmann bromamide degradation converting amide to primary amine with one less carbon — Class 12 Chemistry Chapter 9

Amines Video Walkthrough

Source: Magnet Brains on YouTube

Amines All Important Formulae and Reactions for Class 12 Chemistry

The canonical master table below lists every working formula, named reaction, and quantitative trend in NCERT Chapter 9, with reagents, conditions, section reference, and the typical exam-use cue. All entries below are retained in the 2026-27 syllabus.

Concept / ReactionFormula / EquationConditionsNCERT RefCommon Use
Primary amine general formula R-NH2 or CnH2n+3N (saturated)-9.1Two N-H bonds; count N-H to assign class
Secondary amine R2NH or R-NHR' -9.1One N-H bond
Tertiary amine R3N -9.1No N-H bond
Quaternary ammonium salt R4N+X- -9.1Phase-transfer catalysts, surfactants
N geometrysp3, pyramidal; C-N-C ≈ 108 in (CH3)3N-9.2Lone pair in 4th sp3 orbital
1. Reduction of nitro compound R-NO2 H2/Ni or Fe/HCl R-NH2 H2/Ni, Pd, Pt or Fe/HCl, Sn/HCl, Zn/HCl9.4Fe/HCl preferred; industrial aniline route
2. Ammonolysis of alkyl halide R-X + NH3 EtOH, sealed, 373 K R-NH3+X- NaOH R-NH2 excess NH3, sealed tube9.4Mixture of 1°/2°/3°/quaternary; RI > RBr > RCl
3. Reduction of nitrile (ascent) R-CN LiAlH4/ether or H2/Ni R-CH2-NH2 LiAlH4 dry ether9.4Adds one C (ascent of amine series)
4. Reduction of amide R-CONH2 LiAlH4/ether R-CH2-NH2 LiAlH49.4Preserves C count
5. Gabriel phthalimide synthesis Phthalimide KOH K-phthalimide R-X N-alkyl OH-/H2O,Δ R-NH2 aliphatic R-X only9.4Pure 1° amine, no over-alkylation; aryl X fails
6. Hoffmann bromamide degradation R-CONH2 + Br2 + 4NaOH → R-NH2 + Na2CO3 + 2NaBr + 2H2O aq. Br2/NaOH9.4One C less than amide (chain shrinks)
Salt formation R-NH2 + HCl → R-NH3+Cl- dil. HCl9.6Water-soluble salt; basis for separation
Kb definition Kb = [R-NH3+][OH-][R-NH2]; pKb = -log Kb aq. soln.9.6Smaller pKb = stronger base; NH3 pKb = 4.75
Gas-phase basicity (alkyl) 3 > 2 > 1 > NH3 no solvent9.6Pure +I effect
Aqueous basicity (methyl series) (CH3)2NH > CH3NH2 > (CH3)3N > NH3 in water9.6+I, solvation, steric tug-of-war
Aqueous basicity (ethyl series) (C2H5)2NH > (C2H5)3N > C2H5NH2 > NH3 in water9.63° ahead of 1° for bulkier R
Alkylation (over-alkylation) R-NH2 R'X R-NHR' R'X R-NR'2 R'X R-NR'+3X- R'-X excess9.6Gives mixture; route to quaternary salt
Acylation R-NH2 + R'-COCl pyridine R-NH-CO-R' + HCl pyridine mops up HCl9.61°/2° only (need N-H)
Benzoylation CH3NH2 + C6H5COCl → CH3-NH-CO-C6H5 pyridine9.6N-methylbenzamide; protects -NH2
Carbylamine test (1° only) R-NH2 + CHCl3 + 3KOH Δ R-NC + 3KCl + 3H2O alc. KOH, Δ9.6Foul-smelling isocyanide; identifies 1° amine
HNO2 on 1° aliphatic R-NH2 + HNO2R-OH + N2↑ + H2O NaNO2/HCl9.6Quantitative N2; estimates -NH2 in proteins
HNO2 on 1° aromatic (diazotisation) Ar-NH2 + NaNO2 + 2HCl 273-278 K Ar-N2+Cl- + NaCl + 2H2O 273 to 278 K only9.7Gateway to all Ar-X, Ar-OH, azo dyes
HNO2 on 2° amine R2NH + HNO2 → R2N-N=O + H2O NaNO2/HCl9.6Yellow N-nitrosoamine
Hinsberg test (1°/2°/3°)1°: R-NH2 + PhSO2Cl → PhSO2NHR (NaOH-soluble); 2°: R2NH → PhSO2NR2 (NaOH-insoluble); 3°: no rxnPhSO2Cl + KOH9.6Classic distinguishing test
Bromination of aniline (aq) C6H5NH2 + 3Br2 → 2,4,6-tribromoaniline↓ + 3HBr Br2/H2O, RT9.6White ppt; -NH2 over-activates ring
Controlled p-bromoaniline C6H5NH2 Ac2O acetanilide Br2/CH3COOH p-Br-acetanilide H3O+ p-bromoaniline protect-brominate-deprotect9.6Acetylation reduces ring activation
Nitration of aniline (direct) C6H5NH2 HNO3/H2SO4 47% m + 51% p + 2% o conc. HNO3/H2SO4, 288 K9.6Protonation gives -NH3+ (m-director)
Sulphonation of aniline C6H5NH2 + H2SO4 Δ C6H5NH3+HSO4- 453-473 K p-sulphanilic acid conc. H2SO4, 453 to 473 K9.6Zwitterionic product; high m.p.
Friedel-Crafts on anilinefailsAlCl3 + R-Cl9.6AlCl3 bonds to N; ring deactivated
Sandmeyer (Cl) Ar-N2+Cl- CuCl/HCl Ar-Cl + N2Cu(I) catalyst9.9Higher yield than Gattermann
Sandmeyer (Br) Ar-N2+Cl- CuBr/HBr Ar-Br + N2CuBr/HBr9.9-
Sandmeyer (CN) Ar-N2+Cl- CuCN/KCN Ar-CN + N2CuCN/KCN9.9Only route to Ar-CN from arene
Gattermann (Cl, Br) Ar-N2+Cl- Cu powder/HX Ar-X + N2Cu metal, HCl or HBr9.9Lower yield than Sandmeyer
Iodide (KI) Ar-N2+Cl- + KI → Ar-I + N2↑ + KCl aqueous KI9.9Only route to Ar-I
Schiemann (F) Ar-N2+Cl- + HBF4 → Ar-N2+BF4- Δ Ar-F + N2↑ + BF3 HBF4, dry heat9.9Only route to Ar-F
Reduction to arene (-H) Ar-N2+Cl- + H3PO2 + H2O → Ar-H + N2↑ + H3PO3 + HCl H3PO2 or EtOH9.9Removes -N2+ as -H
Hydroxyl (-OH, phenol) Ar-N2+ + H2O → Ar-OH + N2↑ + H+ warm to 283 K9.9Why diazonium baths kept < 5°C
Nitro (-NO2) Ar-N2+BF4- + NaNO2 Cu Ar-NO2 + N2NaNO2/Cu9.9Via fluoroborate
Coupling with phenol C6H5N2+Cl- + C6H5OH OH-, 0-5 C p-HO-C6H4-N=N-C6H5 mild base, 0 to 5°C9.9p-hydroxyazobenzene (orange dye)
Coupling with aniline C6H5N2+Cl- + C6H5NH2 mild acid, 0-5 C p-H2N-C6H4-N=N-C6H5 mild acid, 0 to 5°C9.9p-aminoazobenzene (yellow dye)

The single highest-frequency CBSE 1-mark slip on this chapter is mixing up Sandmeyer (CuX) with Gattermann (Cu metal + HX): both give the same Ar-X product, but Sandmeyer always wins on yield. Tag every Ar-N2+ question with the reagent first, then choose.

How will Collegedunia's Amines Formula Sheet Help You?

The sheet is built for a 25 to 30 minute final-night revision pass before a Chemistry paper.

  • 2026-27 NCERT Alignment: Every reaction, named reaction, and basicity trend matches the current syllabus print of Sections 9.1 to 9.10.
  • One-Page Printability: The master table fits on a single A4 landscape sheet.
  • Named-Reaction Tagging: Each preparation is tagged Hoffmann, Gabriel, Sandmeyer, Gattermann, Schiemann, Hinsberg, or Carbylamine, with catalyst and product clearly listed.
  • Expert Verification: Cross-checked against NCERT Sections 9.1 to 9.10 and the last five JEE Main and NEET papers.
Exam Hook: Carbon-counting is the secret to amine preparation MCQs: LiAlH4/CN adds +1 C, Hoffmann removes -1 C, Gabriel and amide-LiAlH4 are 0. CBSE has tested "convert butanamide to propan-1-amine" (Hoffmann) and "convert ethanenitrile to ethylamine - wrong, gives methylamine plus CH2" patterns in 4 of the last 5 board papers.

Why Amines Matters in 12th Chemistry and Entrance Exams

The chapter is the final keystone of the entire organic block. Amine chemistry feeds directly into Biomolecules (amino acids, peptide bonds, DNA bases), Drug Chemistry (alkaloid skeletons), and any JEE-level conversion ladder that needs an aromatic substitution at -F, -I, or -CN positions. Named-reaction MCQs on Hoffmann, Gabriel, and Sandmeyer appear in every JEE Main session since 2020 and in every NEET paper since 2021. Students who memorise the carbylamine, Hinsberg, and diazonium tests in their exact reagent form lock in 3 to 5 nearly-guaranteed marks across boards and entrance papers.

Basicity Kb pKb definition and amine basicity orders in water and gas phase — Class 12 Chemistry Chapter 9

Basicity and Reactivity Reference Table for Amines

The trends below power most of the 1-mark MCQs on Chapter 9. JEE Main has asked at least one basicity-ranking question every year since 2021.

CompoundStructurepKbClassKey Note
AmmoniaNH34.75referenceCross-over: pKb < 4.75 is stronger than NH3
MethanamineCH3-NH23.38aliphatic 1°+I of methyl strengthens base
N-Methylmethanamine(CH3)2-NH3.27aliphatic 2°Strongest of methyl series in water
N,N-Dimethylmethanamine(CH3)3-N4.22aliphatic 3°Weakest of methyl series (steric blocks solvation)
EthanamineC2H5-NH23.29aliphatic 1°-
N-Ethylethanamine(C2H5)2-NH3.00aliphatic 2°Strongest of ethyl series
N,N-Diethylethanamine(C2H5)3-N3.25aliphatic 3°3° ahead of 1° in ethyl (bulky steric)
Phenylmethanamine (benzylamine)C6H5-CH2-NH24.70aliphatic 1°-CH2- insulates N from ring
AnilineC6H5-NH29.38aromatic 1°Lone pair delocalised into ring
N-MethylanilineC6H5-NH-CH39.30aromatic 2°-
N,N-DimethylanilineC6H5-N(CH3)28.92aromatic 3°Stronger than aniline (alkyl +I)
p-Toluidinep-CH3-C6H4-NH28.92aromatic 1°EDG -CH3 raises basicity
p-Nitroanilinep-O2N-C6H4-NH213.0aromatic 1°EWG -NO2 drops basicity 5000-fold
Quick Tip: The basicity hierarchy at a glance is aliphatic R-NH2 > NH3 > C6H5-CH2-NH2 (just) > aniline (Ar-NH2). The benzyl group is NOT an aryl group; the -CH2- spacer insulates N from the ring, so benzylamine behaves like an alkylamine and only just slips below NH3. Use this to answer every "which of the following is the strongest base" question.

Top 3 Most-Asked Amines PYQ Topics in CBSE, JEE and NEET

The three patterns below have repeated most often since 2021. The full year-by-year map sits on the Collegedunia NCERT Solutions page.

TopicFrequency (CBSE + JEE + NEET, 2026 to 2021)Typical mark band
Distinguishing tests (Hinsberg, carbylamine, HNO2)14 times2 to 3 marks
Diazonium conversions (Sandmeyer, Schiemann, KI, H3PO2, coupling)12 times2 to 3 marks
Basicity ranking of substituted anilines / alkylamines10 times1 to 2 marks

Full year-wise PYQ map: Amines Class 12 Chemistry NCERT Solutions

Amines Quick-Fact Cards for MCQ Recall

The four facts below are the ones JEE Main and NEET rotate as 1-mark MCQs. Memorise them in this exact form.

Hoffmann shrinks, LiAlH4/CN grows
Hoffmann bromamide: R-CONH2 loses 1 C. LiAlH4 on R-CN adds 1 C. Gabriel and LiAlH4/amide keep C count
1° only = Carbylamine
R-NH2 + CHCl3 + 3KOH gives R-NC (foul smell). 2° and 3° amines do not respond - classic 1° test
Diazotise at 273 to 278 K
Above 5°C the diazonium salt hydrolyses to phenol. Aryl-N2+ is stable in this range, alkyl-N2+ decomposes at once
Gabriel fails for aryl amines
Phthalimide anion does not displace aryl halide (no SN2 on sp2 C). Use Hoffmann or Fe/HCl reduction instead
Watch Out: Direct nitration of aniline gives 47% m-nitroaniline, not pure p-product. The conc. H2SO4 protonates -NH2 to -NH3+, which is a deactivating meta-director. To get clean p-nitroaniline, you must first acetylate (-NH2 to -NHCOCH3), then nitrate, then hydrolyse. Writing "direct HNO3/H2SO4 on aniline gives p-nitroaniline" is a guaranteed 1-mark deduction in CBSE marking schemes.

Amines Common-Numerical Pattern Templates for 12th Chemistry

The four problem setups below have dominated CBSE, JEE Main, and NEET papers since 2021.

PatternWhat the question givesFormula / Rule to applyCommon trap
Distinguishing testTwo amines (1°, 2°, or 3°), name the reagent that tells them apartHinsberg (3-way), carbylamine (1° only), HNO2 (1° aliphatic = N2; aromatic = diazonium)Using carbylamine for 2° or 3° (gives nothing)
Basicity rankingList of substituted anilines or mixed aliphatic/aromatic aminesEDG raises Ar-NH2 basicity; EWG lowers it; aliphatic > NH3 > benzylamine (just) > anilineForgetting that aqueous-phase order differs from gas-phase order
Conversion chain (Ar-X synthesis)"Convert benzene to Ar-F / Ar-I / Ar-CN in N steps"Always go via diazonium: benzene to nitrobenzene to aniline (Fe/HCl) to Ar-N2+ to productTrying direct halogenation for F or I (does not work)
Carbon-counting in prepReagent + substrate, identify product chain lengthLiAlH4/CN: +1 C; Hoffmann: -1 C; Gabriel and LiAlH4/CONH2: 0Saying CH3CN + LiAlH4 gives methylamine (gives ethylamine: +1 C)

One-Shot Revision Tips for Class 12th Chemistry Amines

  • Count the N-H bonds to classify: 2 N-H = 1°, 1 N-H = 2°, 0 N-H = 3°. Faster than counting alkyl groups when the structure is drawn out.
  • Aryl diazonium fluoroborate is the only RT-stable diazonium salt - that's why Schiemann is a two-step (HBF4, then dry heat) and not a one-pot reaction.
  • Friedel-Crafts alkylation / acylation FAILS on aniline because AlCl3 (Lewis acid) coordinates to the N lone pair, making -N+(AlCl3)- a powerful deactivator.
  • Hoffmann bromamide migration is R/Ar from carbonyl C to N: the product amine has the same R group as the starting amide, but one C less. Benzamide gives aniline, not benzylamine.
  • Coupling pH matters: aniline coupling needs mild acid; phenol coupling needs mild base. The base activates phenol (to PhO-, highly o/p-rich); the acid prevents aniline from protonating fully.

Amines Weightage Compared Across Class 12 Chemistry Chapters

Typical CBSE marks distribution across the 10 chapters of the 2026-27 NCERT, averaged over the last five board papers. Amines sits in the mid-tier, similar to Coordination Compounds and Alcohols.

Ch 1 Solutions
7 marks
Ch 2 Electrochemistry
6 marks
Ch 3 Chemical Kinetics
6 marks
Ch 4 d- and f-Block Elements
5 marks
Ch 5 Coordination Compounds
7 marks
Ch 6 Haloalkanes and Haloarenes
4 marks
Ch 7 Alcohols, Phenols and Ethers
5 marks
Ch 8 Aldehydes, Ketones, Carboxylic Acids
6 marks
Ch 9 Amines
5 marks
Ch 10 Biomolecules
4 marks

Related Links:

More Amines Chemistry Class 12 Resources

NCERT Formula Sheet for Class 12 Chemistry: All Chapters

Jump to the formula sheet for any other chapter of Class 12 Chemistry below.

Amines Class 12 Chemistry Formula Sheet FAQs

Ques. Where can I download the Amines Class 12 Chemistry Formula Sheet PDF?

Ans. You can download the Amines Class 12 Chemistry Formula Sheet PDF directly from this Collegedunia page. Both the Normal and HD versions are available and free of cost.

Ques. Is this Formula Sheet aligned with the 2026-27 NCERT?

Ans. Yes. This page reflects the current 2026-27 syllabus for Class 12 Chemistry. Amines is fully retained in the new edition with no formula cuts; every reaction in Sections 9.1 to 9.10 of the NCERT remains examinable.

Ques. How many pages is the Class 12th Chemistry Amines Formula Sheet PDF?

Ans. The Formula Sheet PDF runs approximately 9 pages and covers the master reaction table, symbol glossary, pKb reference, quick-fact MCQ cards, and four common numerical pattern templates.

Ques. What is the difference between Hoffmann bromamide and Gabriel phthalimide synthesis?

Ans. Both produce primary amines but differ in the starting material, the carbon count change, and the substrate scope. Hoffmann bromamide degradation starts from an amide (R-CONH2), uses Br2 with 4 equivalents of NaOH, and the product amine has one carbon fewer than the amide because the R group migrates from carbonyl C to N (alkyl and aryl amides both work). Gabriel phthalimide synthesis starts from phthalimide, alkylates with R-X (SN2), then hydrolyses to give a pure 1° amine with the same carbon count as the alkyl halide; it works only for aliphatic amines because aryl halides do not undergo SN2 on the phthalimide anion.

Ques. Why is aniline a weaker base than methylamine?

Ans. In aniline (C6H5-NH2), the lone pair on nitrogen is delocalised into the aromatic ring through five resonance structures, making it much less available to accept a proton. Once protonated, the anilinium ion (C6H5-NH3+) has only two Kekule resonance structures, so the cation is far less stabilised than the neutral aniline. Methylamine has no such delocalisation - the methyl group is a +I donor that increases electron density on N, so the lone pair is fully available and the methylammonium cation is stabilised by hyperconjugation. Numerically, pKb (aniline) = 9.38 versus pKb (methylamine) = 3.38, a roughly 106-fold difference in Kb.

Ques. Why are aryl diazonium salts stable while alkyl diazonium salts decompose immediately?

Ans. In an aryl diazonium salt (Ar-N2+), the positive charge on the terminal nitrogen is delocalised into the aromatic ring by resonance, spreading the charge over two nitrogen atoms and the ortho/para ring carbons. This delocalisation stabilises the cation enough for the salt to exist in aqueous solution at 273-278 K. In an alkyl diazonium salt (R-N2+), there is no aromatic ring to accept the charge; the localised positive nitrogen is immediately attacked by water or any nucleophile, releasing N2 gas and giving R-OH (or other substitution / elimination products). That is why HNO2 on a 1° aliphatic amine gives R-OH plus a measurable volume of N2, while the same reagent on a 1° aromatic amine gives an isolable diazonium chloride.

Ques. Why does Friedel-Crafts alkylation fail on aniline?

Ans. Friedel-Crafts reactions need a Lewis acid catalyst, typically AlCl3. The nitrogen lone pair of aniline is more basic than a typical aromatic electron pair, so AlCl3 coordinates strongly to N rather than activating the alkyl halide. This generates an Ar-N+H2-AlCl3- complex in which the N now bears a formal positive charge. The aryl ring connected to this strongly electron-withdrawing group is heavily deactivated, so any electrophile (the R+ or RCO+) cannot attack. The standard workaround is to protect the amine as acetanilide (C6H5-NHCOCH3), perform the Friedel-Crafts on the acetanilide, then hydrolyse back to the substituted aniline.

Ques. What is the Balz-Schiemann reaction and how does it appear in the formula table?

Ans. The Balz-Schiemann reaction is the only Class 12 route to aryl fluoride from an aryl diazonium salt. The diazonium chloride (Ar-N2+Cl-) is first treated with HBF4 to precipitate aryl diazonium fluoroborate (Ar-N2+BF4-), which is then heated dry to release N2 and BF3, leaving Ar-F. The formula table lists it as Schiemann under NCERT Section 9.9 with reagent "HBF4, dry heat" and the common-use cue "Only route to Ar-F".

Ques. What is the difference between Sandmeyer and Gattermann reagents?

Ans. Sandmeyer uses cuprous halide (CuCl, CuBr, or CuCN) dissolved in the corresponding halogen acid and gives high yields of aryl halide or aryl nitrile. Gattermann uses copper powder (Cu metal) in HCl or HBr and gives lower-yield aryl halides. Both convert Ar-N2+ to Ar-X (X = Cl, Br), but the catalyst tells them apart in an MCQ: Cu(I) salt = Sandmeyer, Cu metal + HX = Gattermann. The formula table shows both rows side by side under NCERT Section 9.9.

Ques. What is the basicity order of amines in gas phase versus aqueous solution?

Ans. In the gas phase, basicity follows the pure inductive (+I) effect: 3° > 2° > 1° > NH3. In aqueous solution, the order flips because the protonated amine (RnNH(4-n)+) needs N-H bonds to hydrogen-bond with water; fewer N-H bonds means less solvation, which destabilises the conjugate acid. The aqueous order is therefore 2° > 1° > 3° > NH3 for the methylamine series, and 2° > 3° > 1° > NH3 for bulkier ethyl groups. Aromatic amines (aniline) sit far below NH3 because the lone pair delocalises into the ring.

Ques. What is the Hinsberg test and how does it distinguish 1°, 2°, and 3° amines?

Ans. The Hinsberg test uses benzenesulphonyl chloride (C6H5SO2Cl) in aqueous KOH. A primary amine (R-NH2) reacts to give an N-monoalkyl sulphonamide (PhSO2NHR) whose remaining N-H is acidic enough to be deprotonated by NaOH, so the product is soluble in alkali. A secondary amine (R2NH) gives an N,N-dialkyl sulphonamide (PhSO2NR2) with no N-H, so it is insoluble in NaOH. A tertiary amine (R3N) has no N-H to start with and does not react at all - it remains free amine, which on acidification dissolves as the ammonium salt. The three outcomes - NaOH-soluble product, NaOH-insoluble product, no reaction - cleanly separate all three classes in one test.