Organic Chemistry means Ajnish Sir
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Organic Chemistry means Ajnish Sir CH 3 H 3C CH 2 CH 3 X Unsymmetrical Alkene Alkyl halide with rearrangement CH 3 CH3 H 2O/H + H3 C H 3C CH 2 CH 2 HO Unsymmetrical Alkene Alcohol with rearrangement H3 C
1. Hydrohalogenation
2. Hydration
H 3C
3. Oxymercuration demercuration
CH 3 CH 2
CH 3
CH 3 HO Alcohol without rearrangement following Markownikoff rule
BH 3 or B 2H 6
H 3C
–
CH 3 OH
H 2O 2 /OH CH 2 Alcohol without rearrangement Unsymmetrical Alkene following MR but resemble Anti-MR
X2
H 3C Unsymmetrical Alkene
(2)
H 3C
Hg(OAc) 2 /H 2O Na BH 4
CH 3
CH3
5. Halogenation
HX
Unsymmetrical Alkene
H 3C
4. Hydroboration oxidation
CH 3
CH3 X H 3C
X Alkyl dihalide without rearrangement
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Organic Chemistry means Ajnish Sir CH 3
6. Addition of alcohol
ROH/H +
H 3C Unsymmetrical Alkene
H 3C
H 3 C OR Ether with rearrangement
Br
NBS
CH 2 Allyl or benzyl group
7. NBS
CH3
Replacement of allylic or benzylic H with Br
Na/Ether
8. Wurtz reaction
R X Primary or secondary Alkyl halide
9. Corey-House alkane synthesis
R X Alkyl halide
Li
CH 2
R R Alkane
RLi CuI R2CuLi R'–X R R' Alkyl Lithium dialkyl Alkane lithium cuprate Electrolysis
10. Kolbe electrolysis
R COONa R R Salt of mono carboxylic acid Alkane COONa Electrolysis COONa Salt of dicarboxylic acid with single bond COONa Electrolysis COONa Salt of dicarboxylic acid with double bond
H2C CH2 Alkene HC CH Alkyne
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(3)
Organic Chemistry means Ajnish Sir
11. Anti-Markownikoff concept
H3 C
CH3 CH2
CH 3
HBr Peroxide
Br
H 3C
Unsymmetrical Alkene
12. Hydration of alkyne
Alkyl bromide without rearrangement CH3 CH 3 dil. H 2SO 4 H 3C H 3C CH3 HgSO 4 CH O Unsymmetrical Alkyne Ketone without rearrangement H /Ni
13. Hydrogenation
2 R–C C–R or R–CH=CH–R or Pd or Pt R–CH2 –CH2 –R Alkyne Alkene
14. Lindlar catalyst
2 R–C C–R BaSO 4 Alkyne
15. Birch reduction
R–C C–R Alkyne
R
H /Pd
O
16. Clemmensen reduction
(4)
R
cis-alkene R
Na/liq NH 3
R trans-alkene Zn–Hg/HCl
R1 R2 Aldehyde or ketone
R1 R2 Alkane
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Organic Chemistry means Ajnish Sir O
17. Wolf-Kishner reduction
NH 2NH 2 /KOH
R1 R2 Any aldehyde or ketone
O
18. LiAlH 4
OH
R–C–H/R O
LiAlH 4
R–CH/R
O
R–C–X/O–C–R/OR/OH
R–C N
R1 R2 Alkane
LiAlH 4
LiAlH 4
R–CH 2 –OH
R–CH 2 –NH2
O R–C–NH2
LiAlH 4
O
19. NaBH 4
R–C–H/X
R–CH 2 –NH2 OH
NaBH 4
R–CH–R , R–C–R
O R–C–OR/R–C
20. DIBAL-H
O
OH NaBH 4
R–CH–R
O N
DIBAL-H –78°C
R–C–H
DIBAL-H room T
R–CH2 –OH
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Organic Chemistry means Ajnish Sir O
21. Ozonolysis 22. Hydroxylation
R–CH=CH–R'
(i) O 3 (ii) Zn/(CH 3) 2S
O
R–C–H + R'–C–H OH OH
R–CH=CH–R'
dil KMnO 4
R–CH–CH–R
O
23. PCC
R–CH 2 –OH OH R–CH–R
24. KMnO4
PCC
PCC
R–CH 2 OH
R–C–R
KMnO 4
OH
R–COOH O
R–CH–R
C
R–C–H O
KMnO 4
H
R–C–R
COOH
KMnO 4
R
25. Cu/Δ
(6)
R–C–OH CH 3 3° alc
Cu/Δ
R–C=CH 2 R Alkene
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Organic Chemistry means Ajnish Sir O
26. Baeyer-Villiger oxidation
R
O
mcpba
R'
R
OR' Ester
O
27. Tollen’s reagent
R–C–H R–C
Tollen's reagent
CH
Tollen's reagent
O
28. Rosenmund reduction
30. MPV reduction
R1 OR2 Ester O
O R H Aldehyde
Na/ROH
R 1 –CH2 OH + R 2 –OH Alcohol
R H/R Alcohol
Alcohol
OH
Aluminium complex
R H/R Aldehyde or ketone OH
31. Oppenauer oxidation
C – Ag + (White ppt)
R–C
H 2 /Pd-Ba SO 4
R Cl Acid halide O
29. Bouveault-Blanc reduction
R–COO –Ag + (Silver mirror test)
Aluminium complex
R H/R Alcohol O R H/R Any aldehyde or ketone
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Organic Chemistry means Ajnish Sir X
32. Halogenation
X2 /AlCl 3
Aromatic compound
Halogen substituted aromatic compound
NO 2
33. Nitration
conc. HNO 3 /H 2SO 4
Aromatic compound
NO2 substituted aromatic compound SO 3 H
34. Sulphonation
conc.H 2SO 4
Aromatic compound
SO 3H substituted aromatic compound R
35. Friedel-Craft alkylation
R–X/AlCl 3
Aromatic compound
Alkyl substituted aromatic compound
COR
36. Friedel-Craft acylation
RCOX/AlCl 3
Aromatic compound
(8)
RCO substituted aromatic compound
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Organic Chemistry means Ajnish Sir SO 3 H H 2O/H +
37. Protonation
Aromatic sulphonic acid OH
R
OH HNO 2
38. Nitrosation
Phenol
Aromatic compound N
R
R HNO2
OH
NH 2
PhN 2Cl pH 1 0
Phenol
KOH
Phenol
N 2 Ph p-diazophenylaniline
OH
OH CHCl 3
NH 2 PhN 2Cl pH 5
, Aniline N2 Ph p-diazophenylphenol
OH
40. Reimer-Tiemann reaction
R
, NO N,N-dialkyl aniline NO p-nitrosophenol p-nitroso-N,N-dialkyl aniline
OH
39. Diazo-coupling reaction
N
CHO
o-Hydroxybenzene , Phenol carbaldehyde
OH CCl 4
COOH
KOH
o-Hydroxybenzene carboxylic acid
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Organic Chemistry means Ajnish Sir OH
OH COOH
1. CO 2 /KOH
41. Kolbe-Schmidt reaction
2. H +
o-Hydroxybenzene carboxylic acid
Phenol
CHO HCN/HCl
42. Gattermann reaction CHO substituted aromatic compound
Aromatic compound
CHO CO / HCl / AlCl 3
43. Gattermann-Koch reaction CHO substituted aromatic compound
Aromatic compound
CH 2 Cl CH 2O/HCl
44. Chloromethylation
Aromatic compound
Chloromethyl substituted aromatic compound
NH 2
45. Diazotization
N 2 Cl NaNO 2 /HCl 0-5°C
Primary Aromatic amine
(10)
Aromatic diazonium salt
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Organic Chemistry means Ajnish Sir N 2 Cl
X CuX/HX
46. Sandmeyer reaction
Halogen substituted aromatic compound
Aromatic diazonium salt N 2 Cl
X Cu powder/HX
47. Gattermann reaction
Aromatic diazonium salt
Halogen substituted aromatic compound
F
N 2 Cl NaBF4 /Heat
48. Balz-Schiemann reaction
Aromatic diazonium salt CH 3 H 2O
CH 3 –C–Br 1
49. SN reaction
CH 3 Alkyl halide
Flouro substituted aromatic compound CH 3
CH 3 –C–OH CH 3 alcohol with rearrangement
KOH/Acetone
2
50. SN reaction
CH 3 –Br Alkyl halide
CH3 –OH Alcohol without rearrangement
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(11)
Organic Chemistry means Ajnish Sir 51. Williamson ether synthesis
CH 3 –CH 2 OH Alcohol
CH 3– Cl KOH
CH3
CH 3
CH 3 –C–Br EtOH
52. E1 reaction
Δ
CH3 Alkyl halide
CH 3 –C=CH 2 Alkene with rearrangement
CH 3
CH 3 alc. KOH Δ
CH 3 –C–Br
53. E2 reaction
CH 3 –C=CH 2 Alkene without rearrangement with Anti elimination
CH 3 Alkyl halide
CH3 CH 3 Pinacol-pinacolone 54. rearrangement
CH 3 –C
C–CH 3
CH 3 –C–OH
(12)
H+
OH OH 1,2-diol CH3
55. Lucas reagent
CH 3 –CH2 –O–CH 3 Ether via SN 2
CH 3 Alcohol
anhydrous ZnCl 2 /HCl
O CH 3 CH 3 –C–C–CH 3 CH 3 Aldehyde Ketone CH3 CH 3 –C–Cl CH3 Alkyl chloride & test of alcohol
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Organic Chemistry means Ajnish Sir CH 3
CH 3
56. SN 1 reaction of alcohol
Gabril-phthalimide amine 57. synthesis
58. Cyanohydrin formation
CH 3 –C–OH
HBr
CH3 –C–Br CH 3 Alkyl halide with rearrangement
CH 3 Alcohol O
N–H O Phthalimide O
(i) KOH (ii) R–X (iii) H2 O/H+
OH HCN
R–C–H/R
R–C–H/R Aldehyde/ketone
ROH/H
R–C–H/R Aldehyde/ketone O
60. D-Exchange reaction
H 2O/H +
CN Cyanohydrin OH
O
59. Hemiacetal/Acetal formation
R–NH2 1° amine (Preparation of 1° amine)
+
R–C–H/R
D 2O/D + or D 2O/OD –
H/R H 3C Aldehyde or ketone with alpha H
R–C–H/R
COOH α - Hydroxycarboxylic acid OR
ROH/H
OR Hemiacetal
OH
+
R–C–H/R OR Acetal O
H/R DH 2 C Replacement of alpha H with D
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(13)
Organic Chemistry means Ajnish Sir O
OH O
O
Ba se
61. Aldol condensation
H H 3C Aldehyde or ketones with α H
O
62. Cannizzaro reaction
H H 3C β -Hydroxy aldehyde or ketone NaOH
H H Aldehyde without α H
O
63. Perkin reaction
Base
OH
O
H 3C
Br2 /P
OH
Carboxylic acid with α H
(14)
O
X 2 /NaOH
R R CH3 CH 3 Alcohol or aldehyde or ketone with following skeleton
O
65. HVZ reaction
+ H 3C OH H O – Na + Salt of carboxylic acid Alcohol
Ph OH unsaturated carboxylic acid α-β
or
64. Haloform reaction
O
(CH 3CO)2 O/CH 3COONa
Ph H Aromatic aldehyde
H H 3C α -β unsaturated aldehyde or ketone
O
ONa R Salt of carboxylic acid O
+
CHX 3 Haloform
OH Br Replacement of α H with Br
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Organic Chemistry means Ajnish Sir O
66. Decarboxylation reaction
NaOH /CaO
O
67. Hofmann reaction
H
Alkane
Br2 /NaOH
NH 2 R Amide
R
NH 2
Amine
O
68. Grignard reagent
R
R OH Carboxylic acid
OH
O
(i) R–MgX
(i) RMgX
R–C–H/R (ii) H O/H + R–C–H/R , R–C N R–C–R (ii) H 2 O/H + 2 R Alcohol
O
O
OH
R–C–X/O–C–R/OR
(i) RMgX (ii) H 2O
R–C–R R
69. Acid hydrolysis
R–C
O
70. Hunsdiecker reaction
N
H 2 O/H +
O R–C–OH
Br 2
R OAg Silver salt of carboxylic acid
R Br + CO 2 + AgBr Alkyl bromide
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Organic Chemistry means Ajnish Sir Some comments on Ajnish sir by students : Ajnish sir played a key role in my selection in IIT. The way he kept the organic mechanisms and rules in front of me and the way he explained was fabulous. Most important thing that helped me in my preparation were the notes and examples he gave in class. He motivated me at times and was patient enough to handle all my doubts and questions. I am grateful to him being there, when it mattered the most. [Shubham Jain, AIR-56, JEE 2012] Ajnish sir’s rules on organic chemistry helps students easily understand all concepts, reactions, mechanism without need for mugging. [Anurag Talati, University of Alberta, Canada] Awesome teacher...hats off!! [Sharik Sharma] Perfect teacher... [Sunny Tiwary] I love the way you teach chemistry [Amit Mahalwar] Sir you provide content as per our requirement which is great... These podcasts are actually good concept builders. Bhartiya Shishya] Best chemistry teacher i have met till now... [Nishtha Gupta] Organic Chemistry was so tough.... now looks so easy and i am so happy... Abhinav Minocha] You have crystal-clarity about organic chemistry. Your single video can prove... [Vishakha Mehta] A salutation to you and your knowledge and thanks for sharing this... [Sujeet Agrahari] Sir you are God of organic chemistry... [Naveen]
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