ORGANIC REAGENTS

1. Alcoholic KOH 10. CCl4 + OH— (Reimer Tiemann)

R—X ® Alkene (Elimination) OH OH
CO2
2. Aluminium Ethoxide
RCH=O R C O CH2R (Tischenko reaction)
O
11. CO + HCl + AlCl3
(Aldehyde) (Ester)
OH OH
CH O
3. Aqueous KOH/NaOH (Gatterman koch reaction)
R—X ® ROH
Nucleophilic substitution reaction also used for 12. HCN + HCl + AlCl3
Cannizzaro reaction with aldehyde.
OH OH
CH O
4. Baeyer's Reagent (Alkaline cold dilute KMnO4) (Gatterman Aldehyde Synthesis)
RCH=CHR' RCH—CHR'
1, 2 diol 13. CHCl3 + KOH
Alkene OH OH
(Syn) OH OH
(used to detect unsaturation) CH O
(i) (Reimer Tiemann reaction)

5. Bromine water
(i) used to detect unsaturation; (ii) RNH2 ® RNC (Carbylamine reaction)
OH
(used to detect 1° Amine) (Isocyanide test)
NH2 NH2 OH
Br Br Br Br
(ii) (iii)
14. CO2 + OH– (high temp. + Pressure)
Br Br
2,4,6-tribromophenol
OH OH
2,4,6-tribromoaniline
CO2
6. Benedict's solution (Kolbe's reaction)
Used to detect aldehyde group, RCHO ® RCO2–
[ketone gives -ve test]
15. Cu/D
7. Cu2Cl2 + NH4OH (i) RCH2OH ® RCHO,
Used to Detect Terminal Alkyne
(ii) R2CHOH ® R2C=O
Red Precipitate observed
CH3 CH3
8. CrO2Cl2 (iii) H3C–C–OH H2C=C
CH3 CH3
CH3 CH O
(Etard reaction)
16. 2,4 – D.N.P.
9. CrO3 used to detect carbonyl group (orange ppt observed)
(i) RCH2OH ® RCHO,
17. DMSO
(ii) R2CHOH® R2C=O
Polar aprotic solvent: favour SN2 mechanism
(iii) R3COH ® no reaction

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18. Fe+ Br2/FeBr3 28. H2(Ni) can reduce

Br (i) R C R R2CHOH
O
(ii) R–C–H RCH2OH
19. Fehling solution O
used to identify – CH=O group. (iii) RCN ® RCH2NH2; –CºC– ® –CH2–CH2–,
PhCHO gives –ve test –HC=CH– ® –CH2—CH2–
Observation: red ppt of Cu2O formed
29. H2–Pd/BaSO4 or Quinoline
20. Grignard Reagent R C Cl RCH=O (Rosenmund reduction)
Follows (i) Acid base reaction (ii) NAR (iii) NSR O

21. H2(Pd/CaCO3) Quinoline (Lindlar catalyst) 30. Jones Reagent (CrO3+dil. H2SO4+ acetone )
R—CºC—R® R—CH=CH—R (cis) (i) RCH2OH ® R–COOH; (ii) R2CHOH ® R2C=O

22. H3PO2 31. KHSO4 Dehydrating Reagent

+ CH2 CH CH2 OH CH2 CH CH O
N2
OH OH
32. K2Cr2O7/H+
23. HN3 + H2SO4 (i) RCH2OH ® RCO2H; (ii) R2CHOH ® R2C = O

R C OH RNH2 (Schmidt Reaction) 33. MnO2

O (i) CH3—CH=CH—CH2—OH®CH3—CH=CH—CH=O
(ii) PhCH2OH ® PhCH=O
24. H3PO4/D To oxidise allylic / benzylic hydroxyl group into
H3PO4 Þ Same as H2SO4/D corresponding carbonyl.

25. H2SO4/D 34. NaHCO3

14
14
RCH CH3 RCH CH2 RCO2H ¾¾¾¾¾
3 NaH C O
® RCO2- Na + + CO2 ­
OH (Alkene)
Saytzeff product; C+ mechanism; 35. NaHSO3
R OH
26. HNO2 (NaNO2 + HCl) R C R C
R SO3Na+
(i) RNH2 ® R—OH; O
(ii) PhNH2 ® PhN +
(0 – 5°C) [White crystals, soluble in water used to separate
2
carbonyl from noncarbonyl compound]
(iii) PhNH2 ® PhOH (high temperature)
OH OH OH
36. NaOH(aq)
N O (i) R—X ® R—OH
(iv) +
(ii) R C OR' NaOH
(H2O) R C O + R'OH
O O
NO
Basic hydrolysis of ester
27. HIO4 (Periodic acid)
—
(iii) HCHO ¾¾¾
OH
® HCO2- + CH 3OH (cannizzaro)
RCH CH R' RCH=O + R'CH=O
OH OH (iv) H3 C - CH = O ¾¾¾
OH —
® H 3C - CH = CH - CH = O
D
Oxidative cleavage of diol (Aldol condensation)

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37. Ninhydrin
Detection of amino acid 48. Na in Liq. NH3 [Birch reduction]
Observation : Purple coloured ion
R H
R C CR C C
38. NaOR
H R
Strong base :
(trans alkene)
(i) RCH CH2 R RCH CH R
49. OsO4 + H2O
X
(Saytzeff Product : E2 elimination) RCH CHR RCH CH R (syn addition)

OH OH
(ii) H3C C OEt H3C C CH2 C OEt
O O O O3
(claisen condensation) (b keto ester)
50. O3 : R–CH CH–R R–CHO+R–CHO
H 2O\Zn
(Ozonolysis process)

39. NaOH + X2 or NaOX 51. Oxirane followed by H+

RMgX ® RCH2—CH2—OH
(i) RC CH3 RCO2 (Haloform reaction)
-CHI3
O 52. PCC
(i) RCH2OH ® RCHO
(ii) R C NH2 RNH2 (Hoffman Degradation)
(ii) R2CHOH ® R2C=O
O
(iii) R3COH ® no reaction
(Mild oxidizing reagent)
40. NaOH + CaO (Sodalime)
RCO2H ® RH 53. Red(P) + Br2
(i) CH3CO2H ® H2C CO2H (HVZ reaction)
41. MnO / 300°C
Br
used to eliminate CO2 & H2O in 2 mole carboxylic
acids molecule. (ii) ROH ® R —Br

42. NBS 54. P(red) + HI

Br CH3CO2H ® CH3—CH3
CH3CH=O ® CH3—CH3
(i) ; (ii) PhCH3 ® PhCH2—Br CH3CH2OH ® CH3—CH3
(strong reducing agent can reduce any oxygen
or halogen containing compound to alkane)
43. NaNO2 + HCl R–X ® R–H
RNH2 ® R—OH
55. Perbenzoic acid [Baeyer Villiger Oxidation]

44. NaNH2 in paraffin R C R' R C OR'

Non-terminal Alkyne ®Terminal Alkyne O O
(2–Butyne ® 1–butyne) R' having more migrating tendency than R

45. Na/EtOH 56. RCl+AlCl 3 [Friedel craft alkylation]

Reduce all except c/c double & triple bond
R
46. Zn(Hg) + HCl [Clemmensen's reduction]
R C R R CH2 R
O 57. RCOCl + AlCl3 [Friedel craft acylation]

47. NH2 –NH2/OH – [Wolf Kishner reduction] C R

R–CO–R ® R–CH2–R O

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 conc. 64. Tollens Test
58. ROH+R C OH H 2SO 4 R C OR (i) Terminal alkyne gives
Ester
O O (ii) Aldehyde Group gives
(Esterification reaction)
(iii) Ketone gives not give
(iv) a-hydroxy ketone gives
59. SnCl2 + HCl (v) HCOOH gives
NO2
(vi) Hemi acetal gives
NH2
(vii) PhNH–OH gives
(i)
65. Benzene sulphonyl chloride (Hinsberg reagent)
(ii) RCN ® RCH=O [Stephen reduction]
It is used to distinguish and separate 1°, 2° and
3° amines.
60. Sn + HCl
NO2 NH2 66. Tetra ethyl lead (TEL)
(i) Used as antiknocking compound

(ii) RCN ® R–CH2 NH2 67. V2O5

O
61. Silver salt RCOOAg (Hunsdiecker reaction)
V2O 5 /O 2 HC
Br2 (I) O
R - COOAg ¾¾¾® R - Br + CO2 + AgBr
CCl 4 500°C HC
ppt

+ + O
62. AgOH/moist Ag2O; R 4 N X ® R 4 N OH (Maleic anhydride)

OH
63. SOCl2 V2O5 /O 2
(II) 300°C
R C OH R C C
O O
R–OH ® R–Cl

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