IMP Last Minute Revision Formulae Organic Chemistry

Organic Name Reactions
• Aldol Condensation
O
|| OH
CH3– C –H  CH3–CH=CH–CHO

• Claisen Condensation
O O O O O O O
+
EtO H
H 3 C C OEt EtO C CH 2 C CH 3 EtO C CH 2 C CH 3 H C C C OC 2 H 5
H2
OC2 H 5 OEt
• Perkin Condensation
H H O H
O  O
H 3C C ONa
C + HC C C CH 3 C C C OH
O HO O O H
Cinnamic acid
• Benzoin Condensation
O O OH
KCN
2 C H EtOH C CH Benzoin
• Wittig Reaction
CH3 C H3
DMS O
H3 C C O + C H2 P Ph 3 H 3 C C C H 2 + Ph 3 P O
• Haloform Reaction
OH O O
NaOI
H 3 C CH R1 H 3 C C R1
Na OH
CH 3I+R
1
C ONa

I2
• Carbylamine Test
H Cl H Cl OH
CHCl3 
R N C R N C R N C Isocya nide
KO H
H Cl H Cl
• Reimer Tiemann Reaction
H OH H
O
C O
C H Cl 3
KO H
OH O
CCl4
C OH
KO H
H O O
• Kolbe's Schimdt Reaction C
O H 1 25°C OH
NaOH major
CO 2 / H+ O
HO C
225 °
OH
Minor
• Hofmann Bromoamide Degradation
O
|| Br2
R– C –NH2 KOH

 R–NH + K CO
2 2 3
Prof.Motegaonkar S.R. M.Sc.Chem.Gold Medalist SET/NET-JRF,GATE, DRDO,TIFR qualified Page: 1

O
|| NaH3
• Curtius Reaction R– C –Cl  R–NH
H O 2 3
O HN 3 
H3 O
• Schimdt Reaction R C OH H SO R N C O R NH 2
2 4
• Cannizzaro reaction
O O O O O O
50 % slao +
H C H Na OH H 3 C C H C H RDS H C OH+H C H H C ONa +CH 3 OH
H O H H
O
(I) F 3 C C O O H O
O (peracid)
• Bayer villiger oxidation C H 3C C O
H3C (ii) H+
O–O–H
CH3–CH–CH3 CH3–C–CH3 OH
O
O2
+ CH3–C–CH3
• Cumene 130°C
Cumene
hydroperoxide
• Pinacol Pincolone rearrangement
Cl
H
+
+ Ph
-H 2 O Cl C C Cl C C Ph
C C —H +
OH O Ph
OH OH
• Birch Reduction
O
O R(+M) O R C OH COOH
Na/ Na/ Na/
liq. NH 3 ; liq. NH 3 ; liq. NH 3
Na/
R H
R C C R' liq. NH C C Na/ +
3 R C C H liq. NH 3 R C CNa
H R ;
(Acid-base reaction)
trans
• Gabriel Synthesis
O O O O
C NH 3 C KO H C + C H 3-I C
O N H N K N CH 3
C C C C
O O O O
O
H 3O + NH 2 —NH 2
C OH
+ CH 5 NH 2 O
C OH C
O NH
+ H 3 C NH 2
NH
C
O
Page: 2 Prof.Motegaonkar S.R. M.Sc.Chem.Gold Medalist SET/NET-JRF,GATE, DRDO,TIFR qualified
IMP Organic Reagent
1. Alocholic KOH: 6. Benedict's solution
R–X Alkene; Elmination Used to detect aldehyde group RCHO 
2. Aluminium Ethoxide RCO2– [ketone gives –ve test]
RCH = O  R– C –O–CH2 R (Tischenko 7. Cu2Cl2 + NH4OH

||
O Used to Detect Termnal Alkyne
Reaction) Red Precipitate observed
(Aldehyde) (Ester) 8. CrO2Cl2
3. Aqueous KOH/NaOH: CH3 CH=O
R–X ROH
Nucleophilic substitution reaction also used
for Cannizzaro reaction with aldehyde Etard reaction
4. Baeyer's Reagent (Alkaline cold dilute 9. CrO3
KMnO4) i. RCH2OH RCHO,
RCH = CHR' R CH – CH R' ii. R2CHOH R2C = O
| |
OH OH iii. R3COOH no reaction
(Syn) 10. CCl4 + OH– (Reimer Tiemann)

alkene 1, 2 diol
OH OH
(used to detect unsaturation) CO2–
+ p-Product
5. Bromine water
i. Used to detect unsaturation;
11. CO + HCl + AlCl3
NH2 NH2
Br Br OH OH
CH=O
ii. + p-Product
Br
2, 4, 6-tribromoaniline Gatterman koch reaction
12. HCN + HCl + AlCl2
OH OH OH OH
Br Br CH=O
iii.
Br
Gatterman Aldehyde Synthesis
2, 4, 6-tribomophenol

13. CHCl3 + KOH 21. H2(Pd/CaCO3) Quinoline (Lindlar
catalyst)
OH OH
CH=O R–C  C–R R–CH = CH–R (cis)
i.
22. H3PO2
+
Reimer Tiemann reaction N2
ii. RNH2 RNC (Carbyl amine reaction)

(used to detect 1° Amine) (Isocyanide test)
23. HN3 + H2SO4
14. CO2 + OH– (high temp. + Pressure)
R– C  OH RNH2
OH OH ||
– O
CH2 +p-Product
(Schmidt Reaction)
24. H 3
PO4/ :H3PO4 Same as H2SO4/
Koble's reaction
25. H2SO4/ : R CH –CH3 RCH = CH2
15. Cu/ |
OH
i. RCH2OH  RCHO
Satyzeff product; C+ mechanism;
ii. R2CHOH R2C = O
Rearranged alkene can be formed
CH 3
| CH3 26. HNO2 (NaNO2 + HCl)
iii. H3C– C  OH H2C = C
| CH3 i. RNH2 R–OH;
CH 3
ii. PhNH2 PhN2+ (0–5°C)
16. 2, 4-D.N.P.: iii. PhNH2 PhOH (high temperature)
Used to detect carbonyl group (orange ppt
OH OH OH
observed) N=O
17. DMSO : iv. +
Polar solvent: [favour SN2 mechanism]

NO
18. Fe + Br2/FeBr3
27. HNO4 (Priodic acid)
Br
R CH – CH –R' RCH = O + R'CH = O
| |
OH OH
19. Fehling solution : Oxidative cleavage of diol
Used to identify – CH = O group.
28. H2(Ni) can reduce
PhCHO gives – ves test
i. R– C –R R2CHOH
Observation : Red ppt of Cu2O formed ||
O
20. Grignard Reagent
ii. R– C –H RCH2OH
Follows (i) Acid base reaction ||
O
ii. NAR iii. NSR
iii. RCH RCH2NH2; 36. NaOH(aq)
–CC– –CH2–CH2–, i. R–X R–OH
–HC = CH– –CH2–CH2– NaOH
ii. R– C –OR'   R– C –O– + R'OH
29. H2(Pd/BaSO4) || ( H 2O )
||
O O
Quinoline Basic hydrolysis of ester
–
R– C –Cl R CH=O iii. HCHO OH
 HCO2 CH3OH (cannizaro)

||
O OH 
iv. H3C –CH = O  H3C–CH = CH–CH = O
(Rosenmund reduction) 
30. Jones Reagent (CrO3 + dil. H2SO4 + (Aldol condensation)

actone) 37. Nihydrin
i. RCH2OH RCH = O; Detection of amino acid
Observation : Purple coloured ion
38. NaOR Strong Base :
31. KHSO4 Dehydrting Reagent
i. R CH –CH2–R RCH = CH–R
CH 2  CH – CH –OH CH = CH–CH=O |
2 2 X
| |
OH OH
(Saytzeff Product : E2 elimination)
+
32. K2Cr2O7/H ii. H3C– C –OEt H3C – C –CH2– C –OEt
i. RCH2OH RCO2H || || ||
O O O
(claisen condensation) ( keto ester)
33. MnO2
39. NaOH + X2 or NaOX
i. CH3–CH = CH–CH2–OHCH3–CH = CH–CH = O
i. R C –CH3   RCO2– (Haloform reaction)

CHI 3
ii. PhCH2OH PhCH = O ||
O
To oxidise allylic/benzylic hydroxyl group into
corresponding carbonyl. ii. R– C –NH2 RNH2 (Hoffman Degradation)
||
34. NaHCO3 : O
14 14 40. NaOH + CaO

NaH CO3 – +
 RCO2 Na + CO 2 
RCO2H  
RCO2H RH
35. NaHSO3 41. MnO/300°C
OH used for –CO2 & –H2O in carboxylic acid
R– C –R  RC – +
|| SO N
O
3
42. NBS
[White crystals, soluble in water used to Br
separate crbo nyl from noncarbonyl
compound] i.
ii. PhCH3 PhCH2–Br

43. NaNO2 + HCl 53. P(red) + Br2
RNH2 R–OH i. CH3CO2H H2 C  CO2H (HVZ reaction)
|
Br
44. NaNH2 in paraffin
ii. ROH R–Br
Non-terminal Alkyne Terminal Alkyne
(2-Butyne 1-butyne)
54. P(red) + HI
CH3CO2H CH3 –CH3
45. Na/EtOH
CH3CH = O CH3–CH3
Reduce all except c/c double & triple bond
CH3CH2OH CH3–CH3
46. Zn(Hg) + HCl [Clemmensen's (strong reducing agent can reduce any oxygen
reduction] or halogen containing compound to alkane)
R – C –RR–CH2–R 55. Perbenzoic acid ( Baeyer Villi ger
||
O Oxidation)
47. NH 2 –NH 2 /OH – [Wolf Kishner R– C –R' R– C –OR'
|| ||
reduction] O O
R–CO–R R–CH2–R R' having more migrating tendency than R
48. Na in Liq. NH3 [Birch reduction] 56. RCl + AlCl3 [Friedel craft alkylation]
R H
R–C CR  C=C R
H T
(trans alkene)
49. OsO4 + H2O 57. RCOCl + AlCl3 [Friedel craft acylation]
RCH = CHR R CH – CH –R C–R

| | O
OH OH
(syn addition)
conc.
58. ROH + R– C –OH  R– C –OR
H2SO 4
O || ||
50. O3 : R–CH = CH–R 3
R–CHO + R–CHO
H2 O / Zn O O
Ester formed
(Ozonolysis process) (Esterification reaction)
+
51. Oxirane followed by H 59. SnCl2 + HCl
RMgX RCH2 –CH2–OH i. R–N= N–R' RNH2 + R'NH2
52. PCC NO2 NH2
i. RCH2OH RCHO ii.

iii. RCN RCH = O [Stephen reduction]
iii. R3COH no reaction
(Mild oxidizing reagent)

60. Sn + HCl 65. Benzene sulphonyl chloride
NO2 NH2 It is used to distinguish and separate
i. (Hinberg reagent) 1°, 2° & 3° amines.
66. Tetra ethyl lead (TEL)

ii. RCN R–CH2NH2
Used as antiknock compound
61. Silver salt RCOOAg (Hunsdiecer
reaction) 67. V2O5
Br2/CCl4/ RBr + CO2 + AgBr O
  V2O5 /O2 HC
O
62. AgOH/moist Ag2O; R4 NX R N O H i. 500°C
HC
Meleic anhydride O
63. SOCl2
R– C –OH/R–OH R– C –Cl/R–Cl OH
|| ||
O O V2O 5 /O2
ii. 300°C
64. Tollens Reagent Test
i. Terminal alkyne gives
ii. Aldehyde Group gives
iii. Ketone gives –ve test
iv. -hydroxy ketone gives
v. HCOOH gives
vi. Hemi acetal gives
vii. PheNH–OH gives


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Organic Name Reactions

Prof.Motegaonkar S.R. M.Sc.Chem.Gold Medalist SET/NET-JRF,GATE, DRDO,TIFR qualified Page: 1

RCH = O  R– C –O–CH2 R (Tischenko 7. Cu2Cl2 + NH4OH

(Syn) 10. CCl4 + OH– (Reimer Tiemann)

Page: 46 Prof.Motegaonkar S.R. M.Sc.Chem.Gold Medalist SET/NET-JRF,GATE, DRDO,TIFR qualified

ii. RNH2 RNC (Carbyl amine reaction)

Polar solvent: [favour SN2 mechanism]

30. Jones Reagent (CrO3 + dil. H2SO4 + (Aldol condensation)

14 14 40. NaOH + CaO

ii. PhCH3 PhCH2–Br

Page: 48 Prof.Motegaonkar S.R. M.Sc.Chem.Gold Medalist SET/NET-JRF,GATE, DRDO,TIFR qualified

49. OsO4 + H2O 57. RCOCl + AlCl3 [Friedel craft acylation]

RCH = CHR R CH – CH –R C–R

ii. R2CHOH R2C = O

Prof.Motegaonkar S.R. M.Sc.Chem.Gold Medalist SET/NET-JRF,GATE, DRDO,TIFR qualified Page: 49

66. Tetra ethyl lead (TEL)

Page: 50 Prof.Motegaonkar S.R. M.Sc.Chem.Gold Medalist SET/NET-JRF,GATE, DRDO,TIFR qualified

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