Reagents CHemistry
Reagents CHemistry
Colour code: Green = Most important, Yellow = Moderately important, White = Other/reference. This consolidated list merges NCERT-level reagents and reagents commonly
tested in Indian entrance exams (Mains & Advanced).
1 H2 / Pd-C Hydrogenation of C=C/C≡C; reduction of nitro → amine (Hydrocarbons/Amines) RCH=CH2 + H2 → RCH2CH3. Mechanism: Heterogeneous catalytic
hydrogenation (syn addition).
2 H2 / Lindlar catalyst Partial hydrogenation of alkynes → cis-alkenes (Hydrocarbons) RC≡CR' + H2 (Lindlar) → RCH=CHR' (cis). Mechanism: Surface-catalyzed syn
addition.
3 Br2 / CCl4 Halogenation of alkenes (addition); bromination of aromatics (EAS) Alkene + Br2 → vic-dibromo. Mechanism: Electrophilic addition via bromonium
ion.
4 Cl2 / hv or Br2 / hv Free-radical halogenation of alkanes (Hydrocarbons) CH4 + Cl2 --hv--> CH3Cl + HCl. Mechanism: Radical chain
(initiation/propagation/termination).
5 NBS (N-bromosuccinimide) Allylic/benzylic bromination; radical bromination (Hydrocarbons) Allylic H abstraction → allylic bromide. Mechanism: Radical chain via Br•.
6 HBr / HCl (HX) Hydrohalogenation of alkenes (Markovnikov; anti with peroxides) CH2=CH2 + HBr → CH3CH2Br. Mechanism: Electrophilic addition via
carbocation (or radical
with ROOR).
7 Conc. H2SO4 Dehydration of alcohols → alkenes; sulfonation of aromatics; esterification catalyst ROH --conc H2SO4--> R=R' + H2O. Mechanism: E1 dehydration (carbocation) or
E2 for 1° under
some conditions.
8 Dil. H2SO4 / H3O+ Acid-catalysed hydration, hydrolysis, electrophilic additions Alkene + H2O --H+--> alcohol. Mechanism: Electrophilic addition (carbocation
intermediate).
9 KMnO4 (warm/acidic) Strong oxidation: alkenes/alkylbenzenes → carboxylic acids; oxidize alcohols Alkylbenzene → RCOOH. Mechanism: Oxidative cleavage (stepwise electron
transfer/oxygen
insertion).
10 KMnO4 (cold, dilute) Syn dihydroxylation of alkenes to give vic-diols (Hydrocarbons) RCH=CHR' + KMnO4 (cold) → RCH(OH)-CH(OH)R'. Mechanism: Concerted syn
addition.
11 K2Cr2O7 / H2SO4 (acidic dichromate) Oxidation: 1° alcohols → acids; 2° → ketones RCH2OH → RCOOH (1°). Mechanism: Chromate ester formation and elimination
(hydride
transfer-like).
12 PCC / PDC / Swern / DMP Mild oxidations: alcohol → aldehyde/ketone without overoxidation RCH2OH --PCC/DMP/Swern--> RCHO. Mechanism: Formation of activated
oxidant then hydride
transfer.
13 NaBH4 Selective reduction: aldehydes/ketones → alcohols (mild) RCHO + NaBH4 → RCH2OH. Mechanism: Nucleophilic hydride transfer to
carbonyl.
14 LiAlH4 Strong reducing agent: esters, acids, amides → alcohols/amines RCOOR' + LiAlH4 → RCH2OH + R'OH. Mechanism: Hydride transfer
(nucleophilic addition).
15 DIBAL-H Partial reduction: esters → aldehydes (low temp, 1 equiv) RCOOR' + DIBAL-H (−78°C) → RCHO. Mechanism: Controlled hydride transfer
via Al-
coordination.
16 SOCl2 (Thionyl chloride) Convert alcohols → alkyl chlorides; carboxylic acid → acyl chloride R-OH + SOCl2 → R-Cl. Mechanism: Formation of chlorosulfite intermediate →
SN2.
S.No Reagent Uses (functions + chapter) Example reaction + Mechanism
17 PBr3 / PCl5 / PCl3 Convert alcohols → alkyl halides; convert acids → acyl halides (prep) 3 R-OH + PBr3 → 3 RBr + H3PO3. Mechanism: SN2 (inversion for chiral
centres).
18 AlCl3 (Lewis acid) Catalyst for Friedel–Crafts alkylation/acylation (Aromatic EAS) Benzene + RCl --AlCl3--> R–benzene. Mechanism: Electrophile generation →
electrophilic
aromatic substitution.
19 FeCl3 / FeBr3 Catalyst for aromatic halogenation; activate halogens for EAS Benzene + Br2 --FeBr3--> Bromobenzene. Mechanism: Electrophilic aromatic
substitution via
σ-complex.
20 Conc. HNO3 + Conc. H2SO4 Nitration of aromatics (EAS) — generation of NO2+ Benzene + HNO3/H2SO4 → Nitrobenzene. Mechanism: Electrophilic aromatic
substitution via
NO2+.
21 NaNH2 (in NH3) Strong base: elimination to form alkynes; deprotonation of terminal alkynes Vic-dihalide + NaNH2 → alkyne. Mechanism: Sequential E2
eliminations/carbanion formation.
22 NaOH / KOH (aqueous) Saponification of esters → carboxylates; base-catalysed hydrolysis RCOOR' + NaOH → RCOO– + R'OH. Mechanism: Nucleophilic acyl substitution
(basic).
23 NaNO2 / HCl (0–5°C) Diazotization: primary aromatic amines → diazonium salts (Amines) Ar-NH2 + NaNO2/HCl → Ar-N2+Cl–. Mechanism: Nitrosation then conversion to
diazonium.
24 CuCl / CuBr / CuCN (Sandmeyer reagents) Sandmeyer reactions: replace diazonium with Cl/Br/CN etc. Ar-N2+ + CuCl → Ar-Cl. Mechanism: SET/radical displacement (Sandmeyer).
25 HBF4 / BF4– (Schiemann) Conversion of diazonium → aryl fluoride via diazonium tetrafluoroborate Ar-N2+ BF4– → Ar-F (thermal). Mechanism: Loss of N2 and capture by F–.
26 H3PO2 (hypophosphorous acid) Reductive deamination of diazonium salts → Ar-H (deamination) Ar-N2+ + H3PO2 → Ar-H + N2. Mechanism: Reduction with loss of N2.
27 AgNO3 / NH3 (Tollens is Ag(NH3)2+) Tollens test: oxidises aldehydes → carboxylates (silver mirror) RCHO + [Ag(NH3)2]+ → RCOO– + Ag(s). Mechanism: Hydride transfer (redox).
28 Fehling's / Benedict's Tests for reducing sugars/aldehydes (Cu2+ → Cu2O precipitate) Aldehyde + Fehling's → red Cu2O ppt. Mechanism: Redox.
29 2,4-DNP (Brady's reagent) Detects carbonyls (aldehydes/ketones) forming hydrazones RCHO + 2,4-DNP → RCH=N–NHAr (yellow/orange solid). Mechanism:
Nucleophilic addition-
elimination (condensation).
30 NaBH3CN (sodium cyanoborohydride) Selective reductive amination: reduces imines selectively to amines RCHO + R'NH2 + NaBH3CN → RCH2NR'. Mechanism: Imine formation then
hydride transfer.
31 NH2NH2 / KOH (Wolff–Kishner) Deoxygenation: carbonyls → alkanes via hydrazone under basic heat RCOCH3 --NH2NH2/KOH, heat--> RCH2CH3. Mechanism: Hydrazone formation
then elimination
(reduction).
32 Zn(Hg) / HCl (Clemmensen) Reductive removal of carbonyl groups → alkanes (acidic reduction) RCOCH3 --Zn(Hg)/HCl--> RCH2CH3. Mechanism: Metal-mediated reduction
under acidic medium.
33 SO3 / H2SO4 (fuming) (sulfonation) Sulfonation of aromatics (EAS); reversible with steam Benzene + SO3/H2SO4 → benzene sulfonic acid. Mechanism: Electrophilic
aromatic
substitution.
34 mCPBA / peracids Epoxidation of alkenes; Baeyer–Villiger oxidation contexts Alkene + mCPBA → epoxide. Mechanism: Concerted peracid O-transfer (syn).
35 OsO4 Syn dihydroxylation of alkenes → vic-diols (highly chemoselective) Alkene + OsO4 → cis-diol after hydrolysis. Mechanism: [3+2]-like concerted
complexation.
36 O3 (ozonolysis) + Zn/Me2S or H2O2 Oxidative cleavage of alkenes to carbonyl fragments RCH=CHR' --O3, Zn--> RCHO + R'CHO. Mechanism: 1,3-dipolar cycloaddition →
molozonide →
ozonide cleavage.
S.No Reagent Uses (functions + chapter) Example reaction + Mechanism
37 BH3·THF then H2O2/NaOH Anti-Markovnikov hydration of alkenes to give alcohols (syn) CH2=CH2 --BH3/THF; H2O2/NaOH--> CH3CH2OH. Mechanism: Concerted syn
(Hydroboration–oxidation) hydroboration then
oxidation to alcohol.
38 Grignard reagents (RMgX, dry ether) C–C bond formation: add to carbonyls → alcohols; carboxylation with CO2 R-MgBr + CO2 → RCO2MgBr → RCO2H (after acid). Mechanism: Nucleophilic
addition (carbanion-
like).
39 Organolithium reagents (RLi, n-BuLi) Strong base/nucleophile: metalation, deprotonation, C–C bond formation RLi + R'CHO → R-R' (after workup). Mechanism: Nucleophilic
addition/metal–halogen
exchange.
40 Preparation of RMgX / RLi (dry conditions) Preparation prerequisites for organometallics; dry ether/apparatus R-X + Mg → R-MgX in dry ether; R-X + 2Li → R-Li. Mechanism: SET to form
organometallic.
41 Ac2O / RCOCl with pyridine Acetylation/protection of amines & alcohols; prepare esters/amides (protection) R-NH2 + (CH3CO)2O → R-NHCOCH3. Mechanism: Nucleophilic acyl
substitution.
42 HCl / Zn (reduction of nitro) Reduces nitro groups → amines (lab reduction) Ar-NO2 --HCl/Zn--> Ar-NH2. Mechanism: Stepwise electron transfer reductions.
43 SOCl2 / PCl5 (acyl chloride formation) Converts carboxylic acids → acyl chlorides (activation) RCOOH + SOCl2 → RCOCl + SO2 + HCl. Mechanism: Nucleophilic acyl
substitution via
chlorosulfite.
44 NaOEt / EtONa / KOC(CH3)3 (bases) Bases for E2 eliminations and Williamson ether synthesis (SN2/E2) R-CH2-CH2-X + EtO– → Alkene (E2) or Williamson: RO– + R'-X → R-O-R'.
Mechanism: SN2 or E2
depending on substrate.
45 NaH (sodium hydride) Strong base for deprotonation (generate alkoxides for Williamson), hydrogen evolution ROH + NaH → RO– Na+ + H2. Mechanism: Acid-base deprotonation then SN2
for ether formation.
46 Ag2O (silver oxide) Mild oxidant/base; used in some substitution/oxidation tests and Tollens-like reactions Used as mild oxidant/base; mechanism depends on reaction (redox or
base-promoted).
47 Fischer esterification (H2SO4 / heat) Ester formation from acid + alcohol (acid-catalysed) RCOOH + R'OH --H+--> RCOOR' + H2O. Mechanism: Nucleophilic acyl
substitution (acid
catalysed).
48 NaOCl / Bleach Mild oxidant/chlorinating agent in lab oxidations and chlorinations Primary alcohol oxidation under some conditions. Mechanism:
Hypochlorite-mediated
oxidation.
49 Na2CO3 / NaHCO3 Acid neutralisation; distinguishes carboxylic acids by effervescence RCOOH + NaHCO3 → RCOO–Na+ + CO2. Mechanism: Acid-base neutralisation.
50 Lucas reagent (Concd HCl + ZnCl2) Classify alcohols; converts alcohols → alkyl chlorides (SN1 for 2°/3°) 3°-alcohol + Lucas → RCl (fast). Mechanism: SN1 via carbocation (2° slower, 1°
very slow).
51 Pd-BaSO4 / Rosenmund hydrogenation Selective hydrogenation of acyl chlorides → aldehydes (poisoned Pd) RCOCl --H2/Pd-BaSO4--> RCHO. Mechanism: Heterogeneous catalytic
hydrogenation with
poisoned catalyst.
52 Swern oxidation (DMSO, (COCl)2) / PCC / Mild alcohol → carbonyl oxidations without overoxidation (repeat group) RCH2OH --Swern--> RCHO. Mechanism: DMSO activation followed by hydride
DMP abstraction.
53 Acid chlorides (RCOCl) Acylating agents: form esters/amides via nucleophilic acyl substitution RCOCl + R'OH → RCOOR'. Mechanism: Tetrahedral intermediate → elimination.
54 NH3 (excess) Convert acyl chlorides/esters → amides (aminolysis) RCOCl + NH3 → RCONH2. Mechanism: Nucleophilic acyl substitution.
55 Na2Cr2O7 (acidic) Strong oxidant: similar to K2Cr2O7 for alcohol → carbonyl/acid transformations See dichromate oxidations. Mechanism: Chromate ester pathway.
S.No Reagent Uses (functions + chapter) Example reaction + Mechanism
56 HIO4 (periodic acid) Oxidative cleavage of vicinal diols → carbonyl compounds RCH(OH)-CH(OH)R' --HIO4--> RCHO + R'CHO or RCO + R'CHO. Mechanism:
Cyclic periodate ester
followed by cleavage.
57 LDA (LiN(iPr)2) Non-nucleophilic strong base: forms kinetic enolates at low temp (−78°C) Ketone + LDA (−78°C) → kinetic enolate. Mechanism: Fast deprotonation →
enolate.
58 NaH / KOtBu / t-BuOK Strong bases (NaH) and bulky bases (t-BuOK) for deprotonation/E2 (stereoselective) Base-mediated deprotonation → E2 elimination (Hoffmann with bulky base).
Mechanism: Proton
abstraction.
59 t-BuLi / n-BuLi Extremely strong organolithium bases: metalation, deprotonation, form organolithiums Used for metalation/alkynyl formation; mechanism: proton
abstraction/metal–halogen
exchange.
60 Pd catalysts (Pd(PPh3)4) — Cross-coupling C–C bond formation in modern synthesis (JEE-Adv level) Ar-Br + R-B(OH)2 --Pd(0)--> Ar-R (Suzuki). Mechanism: Oxidative addition,
Suzuki/Heck/Stille transmetalation,
reductive elimination.
61 B2Pin2 / R-B(OH)2 (boronic acids) Suzuki partners; borylation reagents for cross-coupling Ar-Br → Ar-B(OH)2 → cross-coupling. Mechanism: Transmetalation in Pd cycle.
62 Wittig reagent (Ph3P=CR2) Wittig reaction converts carbonyls → alkenes (stereoselective control) RCHO + Ph3P=CH2 → RCH=CH2. Mechanism: Formation of
betaine/oxaphosphetane → alkene +
Ph3P=O.
63 Silyl protecting groups (TMSCl / TBDMSCl) Protect alcohols as silyl ethers; deprotect with fluoride (TBAF) ROH + TBDMSCl/imidazole → RO-TBDMS; TBAF removes TBDMS. Mechanism:
& TBAF Nucleophilic
substitution at Si.
64 Appel reagents (PPh3 + CBr4) Convert alcohols → alkyl bromides under mild neutral conditions ROH + PPh3/CBr4 → RBr. Mechanism: Formation of phosphonium intermediate
→ SN2.
65 AIBN / Benzoyl peroxide Radical initiators: thermal decomposition → radicals for chain reactions Initiator → radicals → initiate radical chain halogenation/polymerisation.
Mechanism:
Homolytic cleavage → radicals.
66 R2CuLi (Gilman reagents) / CuI Organocuprates for conjugate additions and substitution of halides (milder than RLi) R2CuLi + R'X → R-R' (coupling) or conjugate addition. Mechanism: Nucleophilic
organocuprate attack.
67 Reformatsky reagent (EtO2C-CH2-ZnBr) Form β-hydroxy esters from aldehydes/ketones via nucleophilic addition Aldehyde + Reformatsky reagent → β-hydroxy ester. Mechanism: Nucleophilic
addition of
organozinc reagent.
68 Dess–Martin periodinane (DMP) / IBX Mild hypervalent iodine oxidants: alcohol → carbonyl (like PCC) RCH2OH --DMP--> RCHO. Mechanism: Formation of iodine(V) intermediate →
hydride transfer.
69 LiAlH(OtBu)3 (selective LAH) Selective hydride reducing agent: esters → aldehydes under controlled conditions RCOOR' + LiAlH(OtBu)3 → RCHO (partial reduction). Mechanism: Controlled
hydride transfer.
70 TfOH / Tf2O (triflic reagents) Strong acids/activators; make triflates (excellent leaving groups) and activate substrates ROH + Tf2O → ROTf (triflate) which is excellent leaving group. Mechanism:
Activation via
triflation.
71 TMSOTf Silyl activation/silylation and glycosylation promoters; Lewis acid Used to activate carbonyls/glycosyl donors; mechanism: silylation/activation.
72 AgNO3 / Ag2O Silver salts: assist halide abstraction, test for halides, oxidant in some cases R-X + AgNO3 → R-Ag/AgX precipitation; mechanism: halide
abstraction/Ag-mediated
substitution.
S.No Reagent Uses (functions + chapter) Example reaction + Mechanism
73 H2O2 (hydrogen peroxide) Oxidant for hydroboration-oxidation workup; green oxidant in many conversions BH2 intermediate + H2O2/NaOH → alcohol. Mechanism: Oxidative conversion
(peroxide
nucleophilic attack).
74 Ph3P=O byproduct (Wittig) Recognise triphenylphosphine oxide as byproduct of Wittig and other P-ylide reactions Formed after Wittig → Ph3P=O. Mechanism: Oxaphosphetane collapse.
75 PPh3 / DEAD (Mitsunobu) Mitsunobu reaction: invert alcohol to other functional groups via nucleophilic ROH + R'CO2H + PPh3/DEAD → R-O-CO-R' (inversion). Mechanism: Formation
substitution of phosphonium
intermediate; SN2-like.
76 HATU / DCC (peptide coupling reagents) Peptide coupling / amide bond formation in synthesis (rare in JEE but included) Carboxylic acid activation → amide. Mechanism: Formation of activated ester /
[advanced] uronium
intermediate.
77 Bromine water / Br2/Fe Electrophilic halogenation of activated aromatic rings; addition to alkenes (aqueous) Phenol + Br2 (aq) → 2,4,6-tribromophenol. Mechanism: EAS via activated ring.
78 Peroxides (ROOR) Initiate radical anti-Markovnikov addition with HBr; radical initiators HBr + Alkene + ROOR → anti-Markovnikov bromoalkane. Mechanism: Radical
chain.
79 CuCl2 / Lindlar? (transition metals for Various metal-catalyzed transformations (context-specific) Used in specialized catalytic transformations; mechanism depends on reaction
special reactions) type.
80 PCC on silica / modified reagents Solid-supported oxidations for cleaner workups (preparative contexts) Alcohol → carbonyl with PCC on silica. Mechanism: Chromate ester oxidation.
81 Phosphorus oxychloride (POCl3) Dehydration/Elimination agent (e.g., Vilsmeier reagent prep) Used to form Vilsmeier reagent or for dehydrations. Mechanism: Activation then
elimination.
82 Vilsmeier reagent (POCl3 + DMF) Formylation of activated aromatics (Vilsmeier–Haack) Aromatic + Vilsmeier → Ar-CHO (formylation). Mechanism: Electrophilic aromatic
substitution via iminium electrophile.
83 Nitric acid mixtures (HNO3/H2SO4) — Nitration contexts (included again for emphasis) See nitration entry.
repeat (nitration)
84 PCC alternative (PDC) Another chromium-based mild oxidant (PDC) for alcohol → carbonyl RCH2OH --PDC--> RCHO. Mechanism: Chromate ester oxidation.
85 Benzenesulfonyl chloride (BsCl) / Tosyl Convert alcohols → sulfonate esters (OTs/OBs) as good leaving groups; protect/activate ROH + TsCl/pyridine → ROTs (better leaving group). Mechanism: Formation of
chloride (TsCl) sulfonate ester
(nucleophilic acyl-like).
86 NaNO2 / HBF4 (Schiemann variant) Alternate route to convert diazonium → Ar-F via BF4 salt (repeat, kept) See Schiemann.
87 H2 / Pd/CaCO3 (poisoned) / Lindlar variants Selective hydrogenation variants for chemoselectivity See Lindlar/Rosenmund contexts.
88 Tollens / silver mirror repeat Analytical test (kept for completeness) See Tollens entry.
89 General acids/bases (H+, OH−; catalysts) General acid/base catalysis underlies many reactions across chapters Acid/base catalysis present in hydration, esterification, eliminations; mech: proton
transfers.
Notes: Example reactions are concise illustrations; consult standard texts for full conditions and safety. If you want a CSV/Excel version or a condensed two-page cheat-sheet
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