ORGANIC REAGENTS S.No. | Reagent Function 1 |PCh, PBrs, Pls ‘Alcohols into Alkyl halides 2 | SoCh,PCls Alcohols into Alkyl chlorides & 3 | HCVZnCl,HBrHI Alcohols into alkyl halides 4___ | ChfFe or FeCl Ci group substituting on Benzene 5___| NaNO; /HCI 0-5°C Diazotisation 6 CuCl,CuBr,CuCN,KI,H,0, H;PO2 Bromo Benzene, Benzo nitrile, lodo Benzene , Phenol,Benzene respectively HBF; or NaBFs oo] AgF or Hg2F, or SbF; or CoF, ‘Alkyl halides into alkyl florides 9 Na/ dry ether Alkyl halides into alkanes 10__| NaOH 623/443/368K Chloro benzene to phenol il Bry /FeBrs Bromination of Benzene 12 | Ch/FeCls Chlorination of Benzene 13 _ | CH-CI/AICI, lation of benzene and its derivatives 14__| CH-CO-CI/AICI, Acylation on benzene 15 | H,SO,4/HNO; Nitration of benzene 16__| (CHCO),0 /AICI; 0 Acylation of Phenol 17__| HSO, ‘ion on Benzene 18 [H,0/HSO, alkenes into alcohols Ag KOH Alkyl halide into alcohol 19 ‘| BH;/H,0,/OH" Alkenes into alcohols (Anti Markownikoff product) 20 —=—| NaBH LiAlH,(LAH) Aldehydes, ketones, acids into alcohols, Nito & Cynides , Isocyanides into amines 21 ‘| Hy Nior HyPd reduction of aldehydes, ketones and 22 [RMgX/H;0* Aldehydes, ketones into alcohls 23 0./H* Cumene to phenol 24 Na Alcohol or phenol into Sodium alkoxide/Phenoxide 25 ‘| (CHCO),0/ CH-CO-Cl O acylation on phenol or N acylation on Aneline or amine 26 = | Conc.H,SO,/443K Conversion of primary alcohols into Alkenes 27___| Conc.H,SO,/410K Conversion of alcohols into Ethers 28 | 85% H;PO,/ 440K Secondary alcohol into alkene 29 | 20% H3PO4/358K. Tertiary alcohol into alkene Alcoholic KOH Alkyl halide into alkeneORGANIC REAGENTS 30 | CrO3/KMn0O, or K;Cr,0;_| oxidation of alcohols into acids in acidic medium 31 | Cu/573k ‘dehydrogenation of alcohols ges r alcohols into aldehydes and 2” alcohols into ketones & 3° alcohos into alkenes 32___| Dil. HNO; Mono nitration of Phenol 33 | Conc.HNO; tri nitration of phenol 34 | Brn /H,0 tri bromination of phenol 35 _| BrafCs2 mono bromination of phenol 36 NaOH /CO2 Phenol to salicilic acid 37 (CHCl /NaOH Phenol to salcilaldehyde 38 | Zn dust Phenol to Benzene 39 NajCr,07 /H2SO, or air Phenol to Benzo quinone 40 Zn/CrO3 200to 300 atm CO & H into methanol 573 673K 41 Invertase Sucrose into Glucose or Fructose 42 Zymase Glucose or Fructose into ethanol 43 HI Ether into alcohol & alkyl halide 44 PCC alcohol to aldehyde 45 Pd /BaSO,,H> acid chloride into aldehyde 46 | SnClyHCI/H,0°" Cyanides into aldehydes 47__| AIH(-Bu),/H,0 Cyanides into aldehydes 48 DIBAL-H/H,O Esters into aldehydes 49 CrO0,CL,/H,0 Toluene to aldehyde 50 | CrO;(CH3;CO),0. Toluene into Benzaldely 51 ‘(Chy/hv Chlorination on alkyl group of Benzene or alkane 52__| CO, HCI anhydrous AICI;_| Benzene to Benzaldehyde 53 | (CHs)Cd acid chloride into ketones 54___| RMgX/H,0* Cyanides into ketones 55 HCN Carbonyl compound into cyanohydrin 56__| NaHSOs addition to aldehyde and ketone 57__|H,NOH carbonyl compound into oxime 58__| HoN-NHo cabot ‘compound into hydrazone 59 H,N-NH-Ph carbonyl compound into Phenyl hydrazone 60 2,ADNP carbonyl compound into 2,4 dinitro phynyl hydrazone 61 H,N-NH-CO-CH; carbonyl compound into carbazide 62 | ROH/HCI Aldehydes & ketones into hemiacetal and acetal 63 HO-CH)-CH>-OH/HC1 Aldehyde or ketone into ethelene glycolORGANIC REAGENTS ketone 64 | Zn-Hg/HCl carbonyl compound into alkane 65 H,N-NH,/KOH carbonyl compound into alkane 66 KMn0,/OH? K,Cr,0; Ketones into mixture of carboxylic acids /H,SO, or HNO; on prolonged oxidation 67__| (Ag(NH3)))NOz+NaOH _| Tollen s test 68 | Cu(OH), Fehiling s test 69 NaOH+), Iodoform 70___| NaOH or Ba(OH), aldal condensation i ‘Conc KOH or NaOH ‘Cannizaro s reaction 72___|KMnO,/KOH Toluene/alkyl Benzene into Benzoic Acid 73 | H,O/H* ‘Cyanides into carboxylic acids, amides into carboxylic acids, esters into carboxylic acis and alcohols, acid chlorides or anhydrides into carboxylic acids 74 NaOH Saponificaiton of ester, acid into salt of acid 75___| NaxCO3 or NaHCO; Carboxylic acid test 76 ~— | PO or P25 Dehydration of acids into anhydride, amides into nitriles 77___ | ROH/conc H,SO4 Caroxylic acids into esters 73 Carboxylic acids into acid chlorides 79 Carboxylic acids into amides 80 | NaOH/CaO Decarboxylation (acids into alkanes) 81 LiAIHy Carboxylic acids into alcohols, amides into amines 82 Ch fred Ps HVZ reaction 83 Sn/HCI or Fe /HCI, H,/Pd | Reduction of nitro compounds into amines 84 NH; Alkyl halides into amines 85 H, Ni or H,/Pd LiAIHy Amides into cyanindes 86__ | KOH/R-X Phthalamide into amine 87 =| NaOH /Br. Hoffman bromamide, amide into amine with one C less 83 KOH,CHCls Amines into Carbyl amines 89 | NaNO/HCI 1° aliphatic into alcohols 90 |NaNO/HCI 05°C Aniline into diazonium chloride 91 | C.H;SO,Cl Distinguishing 1°,2” & 3” amines 92 | Br/H,0 Aneline into tri bromo aniline 93 Br2/ CH-CO-Cl Aniline into Bromo Aniline 4CHCO)0ORGANIC REAGENTS 94 HNO, CH-CO-Cl Nitro aniline 4CHCO),0 95 | H,SO, Sulphonation on aniline 96 | CuCl,CuBr,CuCN,KIH,0, | Diazonium Cholride into Chlor Benzene, HPO, or CH;-CHrOH —_| Bromo Benzene, Benzo nitrile, lodo Benzene , Phenol,Benzene respectivelyNAME REACTIONS [2 | Fintan | CHaBr + Nat —ASEIONE CH + Nabe [>| swe | Cotten lng ST hed nl Friedel-Crafts Alkylation Friedel-Crafts CH CoCr —) Aniydrous AICI 2Na MCC + Oy ——pape ese Hy + Nad a a 7.) Wurta-Fiveig | a ‘OH 8. | Kolbe => a Ca Reimer-Tiermann CHCl + NaGH ——__—__. ———— Williamson CHs-Br + CHy-ONa 9=—H——— CH 1-0-CH, + NaBr H,0" 11) stephen H3C—ON 4 SnCl + HC! —— Hjc—cH =H Se HC —cHoco/ HCI Anhydrous AKI 5 Gatterman ~ Koch Hy Pd / BaSO, Clemmensen in- He HgC—CH y-CH 3 reduction Cone, HO Wolff-Kishner ONH NH, k t HC CH CH reduction Wc” cH, il) KOH / Ethylene glycol ~ Tollens’ test R-CHO+2[Ag(NH).]” + 3 OH ———*R-COO + 2Ag 4 + 2H,0 +4 NH; Fehling’s test R-CHO+2 Cu" + 5 OH" R-COO’ + CuO 4 +3H,0 i 1, / NaOH fodoform CHI [+ CH COO Na nc “ot, OR, Nad! dil NaQH A 2 4y¢ —cHo —— Am HC -CH CH 2 = CHO te CH CH = CCH . NaH HCHO 4 HCHO LORE NAOH coma + Hsc—OH 1) C1, / Red Phosphorus | Hell-volhard- | 4c —-coon 7 H,C——CO0H Bellnehey (HVE i)H,0 I 2 a ° 23.| Hoffmonn Br, tromamide. 3c —t 8», ——————> ¢ nt degradation NaOH24] crite RH, + CHCl; + 3KOH —————™ R-NC + 3KC1 + 3,0 NaNO, + daHCI 273 - 278K '. 1 27. Gatterman CO cus co: "% * OH" 28.| Coupling NiO + — NEN: oH Distinguish By a Single Chemical Test 1. All aldehydes ( R-CHO) give Tollens’ Test and produce silver mirror. RCHO + 2[Ag(NH,),]’ + 30H” RCOO"+ 2Ag | + 2H,0 +4 NH, Tollens' Reagent silver ppt Note; HCOOH(methanoic acid) also gives this test, ketones (RCOR) do not give this test 2. All aldehydes (R-CHO) and ketones{RCOR) give 2,4-DNP test RCOR + 2,4-DNP —> Orange ppt R-CHO + 2,4-DNP — Orange ppt 3. Aldehydes and ketones having CH,CO- (keto methyl) group give lodoform Test. Alcohols having CH,CH- OH group also give lodoform Test. CH,CHO + 31, +4NaQH—> CHI, 4 + HCOONa +3Nal +3H,O Yellow ppt 4, The following compounds give lodoform Test: ethanol (C,H,OH), propan-2-ol {CH,CH(OH)CH,), ethanal{CH,CHO), propanone(CH,COCH,), butanone (CH,COCH,CH,), pentan-2-ane (CH,COCH, CH,CH,), acetophenone ( PhCOCH, } 5. All carboxylic acids (R-COOH) give Bicarbonate Test RCOOH + NaHCO, -+ RCOONa + CO, T + H,0 effervescence 6. Phenol gives FeCl, Test CHOH + FeCl, + (CH.0),Fe + 3HCI (neutral) (violet color)7. 10. 11. 12, All primary amines (R/Ar -NH,) give Carbyl Amine Test R-NH, + CHCl, + KOH(alc) > RNC + KCI + H,O offensive smell Aniline gives Azo Dye Test { Only for aromatic amines) C,H.NH, + NaNO,+HCI > C,H.N,'Cl; then add -naphthol orange dye All alcohols (ROH) give Na-metal test R-OH + Na > R-ONa + H, bubbles For esters (RCOOR) : Hydrolyses first. Then see the products { acid & alcohol) and give a test to identify them. All alkenes (C=C) and alkynes (C=C) decolorizes Br, — water from red to colourless. Lucas Test to distinguish primary, secondary and tertiary alcohols Lucas reagent: ZnCl,/HCl 3°-aleohol + Lucas reagent — immediate turbidity 2"-alcohol + Lucas reagent > turbidity after sometime °-alcohol + Lucas reagent — no turbidity