ORGANIC REAGENTS

ORGANIC REAGENTS
[Link]. Reagent Function 30 Cr0,/KMnOs or K2Cr,01 oxidation of alcohols into acids
PCl, PBr3, Pl Alcohols into Alkyl halides inacidic medium
SoCl2 PCls Alcohols into Alkyl chlorides & dehydrogenation of alcohols gives 1
31 Cu/573k
Carboxylic acids into Acid Chlorides alcohols into aldehydes and 2" alcohols
HCVZnCl, HBr,HI Alcohols into alkyl halides into ketones &3 alcohosinto alkenes
Cl/Fe or FeCl CI group Substituting on Benzene Mono nitration of Phenol
NaNO2 HCI 0-5'C Diazotisation
32 Dil. HNOD
[Link], [Link],H:O, | Diazonium Cholride into Chlor Benzene, 33 [Link] trinitration of phenol
HPO2 | 34 Br,/H,O tri bromination of phenol
Bromo Benzene, Benzo nitrile, lodo
Benzene, Phenol,Benzene respectively 35 Br2/Cs2 mono bromination of phenoi_
| HBF; or NaBF Diazonium Chloride into Floro Benzene 36 NaOH /CO Phenolto salicilic acid
AgF or HgaF2 or SbFs or Alkyl halides into alkyl florides |37 | CHCI/NaOH Phenolto salcilaldehyde
CoF2 38 Zn dust Phenol to Benzene
Na/dry ether Alkyl halides into alkanes 39 NaCrO7 /HSO4 or air Phenol to Benzo quinone
NaOH 623/443/368K Chloro benzene to phenol_
40 Zn/Cr2O, 200to 300 atm CO & H into methanoi
Br FeBr3 Bromination of Benzene 573 6733K
Ch/FeCls |Chlorination of Benzene 41 Invertase Sucrose into Glucose or Fructose
CH C1/AICl; alkylation of benzene and its derivatives 42 Zymase Glucose or Fructose into ethanol
CH CO-Cl/AICl3 Acylation on benzene 43 |HI Ether into alcohol& aikyl halide
H50, /INO, Nitration of benzene 44 |PCC alcoholto aldehyde
16 (CHCO)0/AICl,_ 0 Acylation of Phenol 45 Pd /BaS04,H2 acidchlorideinto aldehyde
H2SO4 Sulphonation on Benzene 46 | SnC1/HCVH,O" Cyanides into aldehydes
47
18 HO/H2SO, alkenes into alcohols 48
AlIH(i-Bu);/H,0 Cyanides into aldehydes
Aq KOH Alkyl halide into alcohol | DIBAL-H/H20 Esters into aldehydes
49
19
BH3/H2O,/OH Alkenes into alcohols (Anti CrO,Cl/H0 Toluene to aldehyde
50
Markownikoff product) 51
CrO,/(CH,CO)%0_ Toluene into Benzaldehyde
20 NaBH/LiAH(LAH)A ketones, acids into alcohóls. Cl/hv Chlorination on alkyl group of Benzene or
INitoCynides, Tsocyanides into amines alkane
21 |H/ Ni or H/Pd reductio of aldehydes, ketones and 52 CO, HCI anhydrous AlCl3 Benzene to Benzaldehyde
53 CHCd acidchloride into ketones
cynides 54
22 RMgX/H,O0 Aldehydes, ketones into alcohls RMgX/H,0 Cyanides into ketone_
| 55 HCN
23 O/H Cumene to phenol Carbonyl compound into cyanohydrin
56 NaHSO
24 Na Alcohol or phenol into Sodium addition to aldehyde and ketone
57 HNOH carbonyl compound into oxime
alkoxide/Phenoxide 58 HN-NH
25 (CHCO)%O/CH-CO-Ci O acylation on phenol or N acylation on 59 HN-NH-Ph
carbonylcompound into hydrazone
carbonyl compound into Phenyl
Aneline or amine hydrazone
26 Conc.H,SO,/443K Conversion of primary alcohols into 60 2,4DNP carbonyl compound into 2,4 dinitro
Alkenes
27
Conc.H2SO4/410K Conversion of alcohols into Ethers | 61 HN-NH-CO-CH3
phynyl hydrazone
carbonyl compound into semicarbazide
28 85%HPO,/440K Secondary alcoholinto alkene 62 ROH/HCl Aldehydes & ketones into hemiacetal and
29 20%H,PO:/358K Tertiary alcoholinto alkene acetal
Alcoholic KOH Alkylhalide into alkene 63 HO-CH2-CH-OH/HCl Aldehyde or ketone into ethelene glycol
 NAME REACTIONS
ORGANIC REAGENTS

ketone Acetone- CH-l NaBr

Zn-Hg/HC carbonyl compound into alkane 1 Finkelstein

CH,Br+ Nal

63
HN-NH KOH carbonyl compound into alkanc -CHF AgBr
66 KMnOOH7 K;Cr:0; Ketones into mixture of carboxylic acids CH,Br AgF
Swarts CH 3
HSOg or HNO on prolonged oxidation
67
Ag(NH):)NO,+NaOH Tollen's test Anhydrous AlCI
69
Cu(OH)2 Fchiling s test_ Friedel-Crafts HC -C
NaOH+ lodoform_ Alkylation
NaOH or Ba(OH)D» aldal condensation coCH
Conc KOH or NaOOH Cannizaro's reaction
KMnOKOH
73 HO/H
Toluenelalkyl Benzene into Benzoic Acid
Cyanides into carboxylic acids, amides
into carboxylic acids, esters into
Friedel-Crafts
Acylation
CH,COd

Anhydrous AC C
carboxylic acis and alcohols, acid 2Na CH 3+ Na
chlorides or anhydrides into carboxylic HC
Wurtz HC- + C-CH Dry e t h e r

acids
74 NaOH
Saponificaiton of ester, acid into salt of
acid 2Na +Na Ci
75 Na,CO or NaHCO | Carboxylic acid test 6. Fittig . Dry ether
76 P4O10 or P20s Dehydration of acids into anhydride,
amidesinto nitriles
77 ROH/conc HSO4 Caroxylic acids into esters 2Na
-CH Na
Wurtz-Fittig
78 PCl3, SoCI PCIs Carboxylic acidsinto acid chlorides + C -CH 3
Dry ether

79 NH3 heating Carboxylic acids into amides

80 NaOH/CaO Decarboxylation (acids into alkanes)
- Na OH
ON a
81 LiAlH Carboxylic acids into alcohols, amides i)co
COOH

into amines |8. Kolbe

82 Ch /[Link] HVZ reaction

Sn /HCI Fe /HCI, H2/Pd | Reduction of nitro compounds into
83 or

amines OH ON a

84 NH3 Alkyl halides into amines CH,Cl Na OH CHO H

C H O

85 H/Ni or H2/Pd LiAIH, Amides into cyanindes Reimer-Tiemann

| Phthalamide into amine

86 KOH/R-X Hoffman bromamide, amide into amine
87 NaOH /Br with one :C less CH -0-CH, Na8Br
CH-Br + CH3-ONa
10 Williamson
88 KOH,CHCl, Amines into Carbyl amines
1 aliphatic amines into alcohols HO
89 NaNO2/HCI Aniline into diazonium chloride HC-CN+ SnCl ,+ HCl HC-CH N
NaNO,/HCI 0 5C 11 Stephen
90 Distinguishing 1",2 & 3 amines
91 CH SOC Aneline into tri bromo aniline
92 Br/HO
Aniline into Bromo Aniline
93 Br/CH-CO-C1
/(CHCO):0
 2 Curbylamine R NH,+ CHCi + 3 KOH
RNC KC2HO
CHO
NaNO,dil HC
Cro ,C Diazo
12. Etard 273 278 K

H0
CHO uC HC
26. Sandmeyer.
/ HCI
13. Gotterman koch
Anhydrous ACI
Cu HC
27. Gatterman
H
14. Rosenmund
HC H
reduction H,C Pd/ BaSOO

15. Clemmensen Zn - Hg 28. Coupling N, + H

HC-CH 2-CH 3
Conc. HCI
reduction CH

Distinguish By a Single Chemical Test

16. Wolff-Kishner
i) NH
, NH
HC-CH 2-CH
reduction CH i) KOH /Ethylene glycol 1. All aldehydes (R-CHO) give Tollens' Test and produce silver miror
RCHO+2[Ag{NH,),] +3 OH>RCO0 2 Ag2HO +4 NH
R-CHO+2 [Ag{NH3)>l 3 OH -R-COO+ 2Ag + 2H0 +4 NH3 Tollens' Reagent silver ppt
17. Tollens' test

+3H20
Note: HCOOH(methanoic acid) also gives thistest, ketones (RCOR) do not give this test
18.1 Fehling's test R-CHO+2 Cu 5 OH -R-COO +
Cu0
2. All aldehydes (R-CHO) and ketones(RCOR) give 2,4-DNP test
NaOH
19. lodoform
C H I + CH CO0 Na RCOR2,4-DNP Orange ppt
CH OR, NaOl R-CHO+2,4-DNP Orange ppt
OH 3. Aldehydes and ketones having CH,CO-(keto methyl) group give iodoform Test. Aiconcls

20. Aldol 2 HC-CHO

dil Nao H C -CH -CH 2-CHO CH3-CH= CHCHO having CH,CH- OH group also give lodoform Test.
HCOONa +3 Nal 3H,0
condensation CH,CHO +31, +4 NaOH CHI,
Yellow ppt
Conc. NaOH
HCOONa+ H3C-OH 4. The following compounds give lodoform Test: ethano! (CH,OH), propan-2-o
Cannizzaro HCHO HCHO
ethanal(CH,CHO), propanone(CH,COCH,)},
butanone (CH COCH,
(CH,CH(OH)CH,),
PhcOCH, )
pentan-2-one (CH,COCH, [Link],), acetophenone (
i) Cl,/Red PhosphoruS
Test
22. Hell-Volhard H,C coOH -
H,C COOH 5. All carboxylic acids (R-CoOH) give Bicarbonate
+ H,O
Zelinsky(HVZ) i) H
RCOOH+NaHCO, > RCOONa +CO
effervescence
Br
Hoffmann H. NH 6. Phenol gives FeCl, Test
bromamide H3C C NH 2

degradation
NaOH
C,H,OH+ FeCl, > (C,H,O),Fe
+
3 HCI
(violet color)
(neutral)
 7. All primary amines (R/Ar NH,) Eve Carbyl Amine Test SCHEME-1:Conversions related to
alkylhalides
R-NH,+ CHCI, KOH{ale) -R-NC KCI H,O RCHCH:.OH 1°alcohol
offensive smell
8. Anifine gives Azo Dye Test
í Onty for aromatic amines) HCHO
RCHCH-OH 2° alcoho!
GH,NH, +
NaNO, HC
CH,N, 'CI; then add B-naphthol orange dye RCHO
All alcohois (ROH) Eive Na-metal test Mg. cther R-CHMgBr[Co
R-OH Na R-ONa + H,
bubbles R - CH2-¢-OH|3°alcohol
10. For esters (RCOOR) :
Hydrolyses first. Then the
R
to identify them.
see
products (acid & alcohol) and give a test
RCH:COOH Carboxylic acid
11. All alkenes (C=C) and alkynes (C=C) decolorizes Br, -

water from red to colourless

12. Lucas Test to distinguish
primary, secondary and tertiary alcohols RCHCHC1+2Na+CICH-CH;R d7 RCH:CH:.[Link]
Lucas reagent: ZnCl/HCI
3-aicohol +Lucas reagent > immediate Alkyl halide Alkane
turbidity
2-aicohoi + Lucas reagent turbidity after sometime R C H CH RCHBr - [Link] RCCH
1-alcohol + Lucas reagent > no turbidity Alkene -2H.O Alkync
aq. KOH RCHCH2OH| 573RCH:CHO Aldehyde
Alcohol
KM1O [Link].
NH
- HCI RCHCHNH2| RCH:COOH Carboxylic acid
Alkyl amine
 SCHEMEll:Conversions relatcd lo ar1l halides
NaOH
sCHEME-1: Conversionsrelated toalcohols
023 K, 00at OONa dl H
Sod phenoxide
-OH
Phenol

RCH CH,OH e H,SOwd_ RCH-CH RCH CH

NHOaK 2 NH -CuCh+H HO

Arl aminc
Alcohol Br Alkene
AKae
L RCH CH:Ci kyl
RCHBr -CH;Br
-

QuCN L halide
Pyridine 475 K
-HCI| NH alc. KOH
Cyanobenzene
Sg cthc - MgB RCH:CHNH| RC=CH
Alkyl amine
Phenyi magnes ium
Cu573K KMnOa
bromide
-H RCH:CHo RCH-COOH
C
2idyehe Aldehyde KCr:0
Carboxylic acid
-u- LiBr KMnO
Phenyl lithium RCH:COOH Carboxylic acid
Aryi halide C-CHr-2Na (O-CH -2NaCT NHvapva/Al:O,
RCH:CHNHa
Toluene Alkyl amine

Ni-AI NaOH 28C

Benzene
C
- - CI
a--a
o- dichlorobenzene p- dichlorobenzene
H:SOA -

SOH
c
- HSOO-a
0 sulphonic acid
p sulphonic acid
-C12Na
2rac
Diphenyl
 SCHEME-IV: Conversion related to phenols-I phenolsI
SCHEME-V;Conversion related to
2Na
ONa+ H Conc. HNO; + NO2
Sod. phenoxide N O O - O H + 3H:0

NaOH NO2
-ONa+ H0 2,4,6-trinitrophenol

Sod. phenoxide (Picric acid)

Zno -OH+ Hc O
Benzcne CC
Anhyd. AlCh
CHs
p - cresol
Ni O-NHa + H:0 cresol
Anlhyd. ZnCC,
675 K Aniline NaOH O-OH (CHCO);0 ocoCH+CHCOOH
CO, 4-7 atm Conc. HSO4 CoOH
[Link] or CoOH
|Kolbe's reaction
(CHCO:0
Pyridine
OocoCH,AIChA OH
+HscOc-O-OH
Salicylic acid Aspirin

OH HCI COCH 3Ha,Ni- - O H

0 phenyl acetate P-phenyl acetate
Cyclohexanol
Bra in CS
O-o Br--OH OH CrOa
0 =0+ HO
Phenol Br P - benzoquinone

o- bromo phenol p- bromo phenol

CHCL,NaOH
340 KHC
3B Br- OH+ 3HBr
Phenol
Rcimcr Ticmann -OH
CHO
reaction
Br
2, 4,6-uribromophenol Salicylaldehyde
CC,NaOHA
Dil. HNO NO:-O-oH 340 KHC
|Rcmcr Ticmann OH
COOH
NO reactuon
anitrophenol P-nitrophenol Salicylic acid

Conc. HSO, FeCh

288-293 K -o
SO:H
0)re
Ferric phenoxide
fe+ 3HCI

2- hydroxy benzene
sulphonic acid N,CI

Conc. HS04
NaOH O-N=N-O)-0H 1HCI
373 K HSOO)-oH p-Hydroxy azobenzene
4-hydroxy benzenc
sulphonicacid
sCHEME-V1: Conversion related to aldehydes
SCIIEME-VI:Conversion related to carboxylicacids

RCH:CHO Clemmensen Rodurtion RCH CH PCls or PCh or SOCh

Zn (Hg) H C
RCHCOCI Acid chioride
-

Akdchyde Alkane |RCH COOH |

L
Wol Krdhnr Rehichon NH
Carboxylic acid
NH NH+ KOH
glbol NH
RCHCONH; Acid amide
R'OH RCH2COOR|
HN [Link]
A BreKOH
RCH-CH;OH RCH CH Alkane Conc. H2S04
Ester Hoffmann
Alcohol Br Bromamide
reaction
PCls
RCHBr-CHBr CaO+NaOH/A
KMoO
RCH-COOH CH| RCH2NH2
|RCH-CH:c
RCH:CH Alky
halide alc. KOH Alkanc Aminc

-HC| NH RC=CH
LiAIHA or B:H«
Alkyne
RCH:CH:NH:Alkyne amine RCHCH:OH
Alcotol

Clemmensen Reduction
Zn(Hg)+HC
RCH:CH:
Wolff Kishner Reduction AlkanE
NHa- NH:+KOH glycol
Or
H1/Red P

NH2/Ni RCH:CHO
Quinoline
Aldebyde
SCHEME-VTI: Conversion related to alkyl amines SCHEME-VIlI: Conversion related to aryl amines
4R1
RCH: NH: RAHNT ArOH Phenol
Árnine Teaa alkey
anonrum CuCN
odide Ar-CN Cyanobenzene
RCOCTRCH:NHCOR Ki,A Ar lodobenzene
Aimde
HBF4
r - F Faroee
R-C-0-C-R
RCOOH
CaBr Ar-Br Bromobenzene
RCH:NH-C-R| NaNO+ HC C
Acd amde
Carbaxyic acid ArNH 0-5° C R A r -C [Link]
Aryl Diazonrum
amine Chloride HBF
NaNO Ar-NONitrobenzene
RCHNH-CO|
AMde

HPOHOAr-HBenzene
R'CHO
RCH NR
- R- 0-N=N-O-R
Schiff's baSe Azodye
NaSH
CHCL 3KOH{alc.) -A-SH Thioghenol
Carbylamine reaction RCH: NC+3KCI -3H0
Isacyanide
HNO:
RCH:OH ASCENDING SERIES
Aloauhot

(1)By Wurtz Reaction

S=C=S/A
RCH:NH-C-SH|
Dithuoalkryl carbamac
HgChRCH:-N=
Hcat
Alky
R-X+2Na+X-R Dry R-R +2Na
acd 1sthiocyanale

C-CCI
R-CH:-NH-(NH-CH:-R RX2Na+X-R R R NaN
Symn. disubstituued urea

(2) By Using Cyanide

alk. KMn
RCH:NHOH R-CH-N=0 R-CH:NO|
wwwwwmvm

lydroryl Niroso Noro conpound

compnnd