Organic Reagents: 1. Alcoholic KOH 2. Aluminium Ethoxide

Chapter 23
Organic Reagents
1. Alcoholic KOH
R–X → Alkene; Elimination
2. Aluminium Ethoxide
R–C–H = O → R–C–O–CH2R (Tischenko Reaction)
O O
(Aldehyde) (Ester)
3. Aqueous KOH/NaOH
R–X → ROH
Nucleophilic substitution reaction also used for Cannizzaro reaction
with aldehyde.
4. Baeyer’s Reagent (Alkaline cold dilute KMnO4)
RCH = CHR’ → RCH–CHR'
OH OH
(Syn)
alkene → 1, 2 diol
(used to detect unsaturation)
5. Bromine water
(i) Used to detect unsaturation;
NH2 NH2 OH OH
Br Br Br Br
Br2(aq.) Br2(aq.)
(ii) (iii)
Br Br
2,4,6-tribromoaniline 2,4,6-tribromophenol
6. Benedict’s solution
–
Used to detect aldehyde group RCHO → RCO2 [ketone gives –ve test]
7. Cu2Cl2 + NH4OH
Used to Detect Terminal Alkyne
Red Precipitate observed
8. CrO2Cl2
CH3 CH=O
Etard reaction
9. CrO3
(i) RCH2OH → RCHO,
(ii) R2CHOH → R2C=O
(iii) R3COH → no reaction
– –
10. CCl4 + O H (Reimer Tiemann)
OH OH
–
CO2
+ p-Product
11. CO + HCl + AlCl3

OH OH O
C–H
+ p-Product
Gatterman koch reaction

12. HCN + HCl + AlCl3
OH OH
CH=O
Gatterman Aldehyde Synthesis

13. CHCl3 + KOH
OH OH
CH=O
(i)
Reimer Tiemann reaction

(ii) RNH2 → RNC (Carbyl amine reaction)
(used to detect 1º amine) (Isocyanide test)
–
14. CO2 + OH (high temp. + Pressure)
OH OH
–
CO2 + p-Product
Kolbe's reaction
15. Cu/D
CH3 CH3
(iii) H3C–C–OH H2C=C
CH3
CH3
16. 2,4 - D.N.P.
Used to detect carbonyl group (orange ppt. observed)
17. DMSO
Polar aprotic solvent: favour SN2 mechanism.
18. Fe + Br2/FeBr3
Br
19. Fehling solution

O
Used to identify –C–H group.
PhCHO gives –ve test
Observation: red ppt. of Cu2O formed
20. Grignard Reagent
Follows (i) Acid base reaction (ii) NAR (iii) NSR
21. H2(Pd/CaCO3) Quinoline (Lindlar catalyst)
R – C ≡ C – R → R – CH = CH – R (cis)
22. H3PO2
N2+
23. HN3 + H2SO4

R–C–OH RNH2
O
(Schmidt Reaction)
24. H3PO4/D
H3PO4 ⇒ Same as H2SO4/D
25. H2SO4/D
RCH–CH3 RCH = CH2
OH
+
Saytzeff product; C mechanism;
Rearranged alkene can be formed
26. HNO2 (NaNO2 + HCl)
(i) RNH2 → R – OH;
+
(ii) PhNH2 → PhN2 (0 – 5ºC)
(iii) PhNH2 → PhOH (high temperature)
OH OH OH
N=O
(iv) +
NO
27. HIO4 (Periodic acid)
RCH–CH–R RCH=O + R'CH=O
OH OH
Oxidative cleavage of diol
28. H2(Ni) can reduce

(i) R–C–R R2CHOH
O
(ii) R–C–H RCH2OH
O
(iii) RCN → RCH2NH2; –C≡C– → –CH2–CH2–,
–HC = CH– → –CH2 –CH2–
29. H2(Pd/BaSO4)
Quinoline
R–C–Cl RCH=O
O
(Rosenmund reduction)
30. Jones Reagent (CrO3 + dil. H2SO4 + acetone)

(i) RCH2OH → RCHO; (ii) R2CHOH → R2C = O
31. KHSO4 Dehydrating Reagent
CH2–CH–CH2–OH CH2=CH–CH=O
OH OH
+
32. K2Cr2O7/H
(i) RCH2OH → RCO2H; (ii) R2CHOH → R2C = O
33. MnO2
(i) CH3–CH = CH–CH2–OH → CH3–CH = CH–CH = O
(ii) PhCH2OH → PhCH = O
To oxidise allylic/benzylic hydroxyl group into corresponding carbonyl.
34. NaHCO3
14 14
–
RCO2H NaHCO3
RCO2Na+ + CO2↑
35. NaHSO3
OH
R–C–R RC – +
SO3 Na
O
[White crystals, soluble in water used to separate carbonyl from
noncarbonyl compound]
36. NaOH(aq)
(i) R–X → R–OH
NaOH –
R–C–OR'
(ii) (H2O) R–C–O + R'OH
O O
– –
(iii) HCHO OH
HCO2 + CH3OH (cannizaro)
–
OH
(iv) H3C–CH = O ∆ H3C–CH = CH–CH = O
(Aldol condensation)
37. Ninhydrin
Detection of amino acid
–
O O
O
C OH C
C + –NH2 → –N
C OH C
O
O O
Observation: Purple coloured ion
–
O O
or –N
O O
O –
O O O
OH C
+ HO → –N
OH H–N
O O O
Yellow orange product
38. NaOR
Strong base:
(i) RCH–CH2–R RCH=CH–R
X
(Saytzeff Product : E2 elimination)
(ii)
H3C–C–OEt H3C–C–CH2–C–OEt
O O O
(claisen condensation) (b keto ester)
39. NaOH + X2 or NaOX
–
(i) RC–CH3 –CHI3 RCO2 (Haloform reaction)
O
R–C–NH2
(ii) RNH2 (Hoffman Degradation)
O
40. NaOH + CaO
RCO2H → RH
41. MnO / 300ºC
Used for –CO2 & –H2O in carboxylic acid.
42. NBS
Br
(i) ; (ii) PhCH3 → PhCH2–Br
43. NaNO2 + HCl

RNH2 → R–OH
44. NaNH2 in paraffin
Non-terminal Alkyne → Terminal Alkyne
(2-Butyne → 1-Butyne)
45. Na/EtOH
Reduce all except c/c double & triple bond
46. Zn(Hg) + HCl [Clemmensen’s reduction]
R–C–R R–CH2–R
O
–
47. NH2 –NH2/OH [Wolf Kishner reduction]
O
R–C–R → R–CH2–R
48. Na in Liq. NH3 [Birch reduction]
R H
R–C≡CR H C=C R
(trans alkene)
49. OsO4 + H2O
RCH=CHR RCH–CH–R
(syn addition) OH OH
O3
50. O3: R–CH=CH–R H2O\Zn R–CHO+R–CHO
(Ozonolysis process)
+
51. Oxirane followed by H
RMgX → RCH2–CH2–OH
52. PCC
(iii) R3COH → no reaction
(Mild oxidizing reagent)
53. P(red) + Br2
(i) CH3CO2H H2C–CO2H (HVZ reaction)
Br
(ii) ROH → R–Br
54. P (red) + HI
CH3CO2H → CH3–CH3
CH3CH = O → CH3–CH3
CH3CH2OH → CH3–CH3
(strong reducing agent can reduce any oxygen or halogen containing
compound to alkane)
55. Perbenzoic acid [Baeyer Villiger Oxidation]
R–C–R' R–C–OR'
O O
R’ having more migrating tendency than R
56. RCl + AlCl3 [Friedel craft alkylation]
R
57. RCOCl + AlCl3 [Friedel craft acylation]
C–R
O
Conc.
58. ROH+R–C–OH H2SO4 R–C–OR
O O
Ester formed (Esterification reaction)
59. SnCl2 + HCl
(i) R–N=N–R’ → RNH2 + R’NH2
NO2 NH2
(ii)
(iii) RCN → R–CH2NH2

60. Sn + HCl
NO2 NH2
(i)
(ii) RCN → R–CH2NH2

61. Silver salt RCOOAg (Hunsdiecker reaction)
Br2/CCl4/D → RBr + CO2 + AgBr
+ – + –
62. AgOH/moist Ag2O; R4NX→ R4NOH
Br2/CCl4/D → RBr + CO2 + AgBr
63. SOCl2
R–C–OH/R–OH R–C–Cl/R–Cl
O O
64. Tollens Reagent Test
(i) Terminal alkyne gives
(ii) Aldehyde Group gives
(iii) Ketone gives –ve test
(iv) a-hydroxy ketone gives
(v) HCOOH gives
(vi) Hemi acetal gives
(vii) PhNH–OH gives
65. Benzene sulphonyl chloride
It is used to distinguish and separate (Hinsberg reagent) 1º, 2º and 3º
amines.
66. Tetra ethyl lead (TEL)
Used as antiknock compound
67. V2O5
O
V2O5/O2 HC
500ºC
O
(i) HC
O
(Maleic anhydride)
OH
V2O5/O2
(ii) 300ºC
qqq

Organic Reagents: 1. Alcoholic KOH 2. Aluminium Ethoxide

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Organic Reagents: 1. Alcoholic KOH 2. Aluminium Ethoxide

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Chapter 23

11. CO + HCl + AlCl3

Gatterman koch reaction

Gatterman Aldehyde Synthesis

Reimer Tiemann reaction

19. Fehling solution

23. HN3 + H2SO4

28. H2(Ni) can reduce

30. Jones Reagent (CrO3 + dil. H2SO4 + acetone)

(i) ; (ii) PhCH3 → PhCH2–Br

43. NaNO2 + HCl

(iii) RCN → R–CH2NH2

(ii) RCN → R–CH2NH2

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