NAME REACTIONS

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 Contents
• Wolff Kishner reduction/ Hung-milnon reaction
• Cannizzaro's reactions
• Aldol Condensation
• Claisen-Schmidt reaction
• Schmidt reaction
• Diazotization reaction
• Stephen’s reaction
• Finkelstein reaction
• Wurtz reaction
• Corey-House Synthesis
• Meerwein -Ponndorf-Verley (MPV) Reduction
• Pinacol-pinacolone Rearrangement
• Beckmann rearrangement
• Friedel-Crafts Reaction
• Reimer-Tiemann Reaction
• Williamson’s Synthesis
• Rosenmund’s Reduction
 Contents
• Clemmensen’s Reduction
• Hofmann Bromamide Reaction
• Claisen Condensation
• Mendius Reaction
• Mannich Reaction
• Kolbe’s Reactions or Kolbe’s Electrolysis
• Wagner Rearrangement
• Birch Reduction
• Sabatier-Senderen’s Reaction
• Gabriel Phthalimide Synthesis
• Diels-Alder reaction
• Curtius Rearrangement
• Perkin Reaction
• Etard Reaction
 Wolff Kishner reduction/ Hung-milnon reaction

H2NNH2 C2H5ONa, 200oC

C=O C=NNH2 Glycol
CH2 + N2
-H2O
Hydrazone Methylene
group

Starting materials Catalyst End product

Aldehydes and C2H5ONa; Glycol Corresponding alkane
ketones + H2NNH2
 Cannizzaro's reactions
2HCHO + NaOH HCOONa + CH3OH
Formaldehyde 50% Sodium Methyl
formate alcohol

Starting materials Catalyst End product

Aldehydes Conc. Alkali Salt of carboxylic
(without α- acids + 1o alcohol
hydrogen)
 Aldol Condensation
H H
Dil. NaOH
CH3 C O + H CH2CHO CH3 C CH2CHO
or K2CO3 3-Hydroxy butanal
Acetaldehyde Acetaldehyde OH
(Two molecules of ethanal) [Aldol (Acetaldol)]
H -H2O
CH3 C CHCHO
But-2-enal
Starting materials Catalyst End product
carbonyl NaOH, Ba(OH)2 or Aldol and Unsaturated
compounds K2CO3 aldehyde or ketone
 Claisen-Schmidt reaction
HH
NaOH
C6H5CHO + H2HC-CHO C6H5C=C-CHO
-H2O
Benzaldehyde Acetaldehyde Cinnamaldehyde

Starting materials Catalyst End product

aliphatic aldehyde Dil. NaOH α,β-unsaturated
or ketone (with α- compound
hydrogen)
 Schmidt reaction

Conc. H2SO4
R-CHO + N3H R-CN + N2 + H2O
Hydrazoic ∆
Alkyl
acid cyanide

R
Conc. H2SO4
R-C=O + N3H R-CONH-R + N2
Hydrazoic ∆
N-alkyl
acid alkanamide
 Conc. H2SO4
R-COOH + N3H R-NH2 + CO2 + N2
Hydrazoic ∆
Primary
acid amine

Starting materials Catalyst End product

Carbonyl conc. H2SO4 Alkyl cyanide, N-alkyl
compounds formamide and 1o amine
 Diazotization reaction
NH2 N=NCl

0-5oC + 2H2O + NaCl

+ NaNO2 + 2HCl

Aniline Benzene diazonium

chloride
Starting materials Catalyst End product
aromatic primary NaNO2; HCl Diazonium salt
amine
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 Stephen’s reaction
SnCl2 H2O
R-C≡N + 2H R-CH=NH . HCl R-CHO + NH4Cl
Alkyl HCl Imine H+
Aldehyde
cyanide hydrochloride

Starting materials Catalyst End product

Alkyl cyanide SnCl2 and HCI Aldehyde
 Finkelstein reaction
Acetone
C2H5Br + NaI C2H5I + NaBr
Ethyl Ethyl iodide
bromide

Starting materials Catalyst End product

alkyl bromides or sodium iodide in Alkyl iodides
chlorides acetone or
methanol
 Wurtz reaction
Dry ether
CH3-I + 2Na + I-CH3 CH3-CH3 + 2NaI
Methyl Ethane
iodide

Starting materials Catalyst End product

Alkyl halide Dry ether Alkane
 Corey-House Synthesis
(CH3)2CuLi + BrC2H5 CH3CH2CH3 + CH3Cu + LiBr
Lithium Ethyl Propane
dimethyl bromide
cuprate

Starting materials Catalyst End product

Alkyl halide - Alkane
Meerwein -Ponndorf-Verley (MPV) Reduction

R [(CH3)2CHO]3Al R
C=O + 2H CH-OH
R in (CH3)2CHOH R
Ketone Sec. alcohol (2o)

Starting materials Catalyst End product

Ketones [(CH3)2CHO]3Al; 2o alcohol
(CH3)2CHOH
 Pinacol-pinacolone Rearrangement

CH3 CH3 CH3 CH3

H3C Mg/Hg
CH3 C HOH
C=O Benzene
C CH3 CH3 C C CH3
H3 C as solvent
O O OH OH + Mg(OH)2
Mg 2, 3-dimethyl butane-2,
3-diol (pinacol)
 CH3 CH3 CH3

CH3 C C CH3 CH3 C C CH3

OH OH CH3 O
Pinacol 3, 3-dimethyl butan-2-one
(Pinacolone)

Starting materials Catalyst End product

Ketones Mg/ Hg; mineral acid 2,3-dimethyl butane-2,3-
dilol(Pinacol); 3,3-
dimethyl butan-2-one
(Pinacolone)
 Beckmann rearrangement
O
H3C SOCl2
C=NOH CH3 C NH CH3
H3 C Ether
Acetoxime N-methyl acetamide

Starting materials Catalyst End product

Oximes conc. H2SO4, PCl5, N-alkyl alkanamide
H3PO4, SOCl2 or
C6H5SO2Cl
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 Friedel-Crafts Reaction
OCH3 OCH3 OCH3
CH3
AlCl3 +2 HCl
2 + 2 CH3Cl Anhyd. +
p-Methylanisole
(Major)
Anisole 2-Methoxy toluene or o-
Methylanisole (Minor) CH3
Starting materials Catalyst End product
Anisole Anhydrous AlCl3 o- and p-methyl
anisole
 Reimer-Tiemann Reaction
OH OH
CHO
65o
+ CHCl3 + 3NaOH + 3NaCl + 2H2O

Phenol o-Hydroxy benzaldehyde

(Salicyldehyde)
Starting materials Catalyst End product
Phenol and NaOH or KOH salicylaldehyde
Chloroform
 Williamson’s Synthesis
55o
C2H5ONa + C2H5I C2H5OC2H5 + NaI
Sodium ethoxide Ethyl iodide Diethyl ether

Starting materials Catalyst End product

Alkyl halide C2H5ONa or dry Ag2O Ether
 Rosenmund’s Reduction
Pd/ BaSO4,
R-C=O + H2 Boiling xylene R-C=O + HCl
Cl H
Acid chloride Aldehyde

Starting materials Catalyst End product

Acid chlorides Pd/ BaSO4; boiling Aldehydes
xylene
 Clemmensen’s Reduction
Zn-Hg
CH3-CHO + 4H CH3-CH3 + H2O
Conc. HCl
Acetaldehyde Ethane
Zn-Hg
CH3-CO-CH3 + 4H CH3CH2CH3 + H2O
Conc. HCl
Acetone Propane
Starting materials Catalyst End product
Aldehyde & Zn-Hg/ conc. HCl Alkane
ketone
 Hofmann Bromamide Reaction
Heat
RCONH2 + Br2 + 4KOH R-NH2 + 2KBr + K2CO3 + 2H2O
Acid amide Primary
amine
Starting materials Catalyst End product
Acid amides Br2; KOH 1o amines
 Claisen Condensation
C2H5ONa
CH3COOC2H5 + CH3COOC2H5 Or (Na)
CH3COCH2COOC2H5 + C2H5OH
Ethyl acetate Ethyl acetoacetate
(Acetoacetic ester)
Starting materials Catalyst End product
Ethyl acetate C2H5ONa ethyl acetoacetate
 Mendius Reaction
H2/ Raney Ni
R-C≡N + 4[H] Or LiAlH4
R-CH2NH2
Alkyl nitrile Primary amine

Starting materials Catalyst End product

Alkyl nitriles H2/ Raney Ni or 1o amines
LiAlH4
 Mannich Reaction
LiAlH4
R-CONHR’ + 4[H] R-CH2NHR’ + H2O
N-Alkyl acid amide Secondary amine

Starting materials Catalyst End product

N-substituted LiAlH4 2o amines
amides
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 Kolbe’s Reactions or Kolbe’s Electrolysis
Electrolysis
2R-COOK + 2H2O R-R + 2CO2 + 2KOH + H2
Electrolysis
2CH3-COOK + 2H2O CH3-CH3 + 2CO2 + 2KOH + H2
Potassium acetate Ethane

Starting materials Catalyst End product

RCOOK or - Alkanes
RCOONa
 Wagner Rearrangement
CH3 CH3
Conc. H2SO4
CH3CH2 C CH CH3 ∆, H O CH3CH2 C C CH3
2
CH3OH CH3
3, 3-Dimethyl pentan-2-ol 2, 3-Dimethyl pent-2-ene

Starting materials Catalyst End product

Alcohol Conc. H2SO4 Alkene
 Birch Reduction
Li, Na/ Liq. NH3 R-C-H
R-C≡C-R + H2
H-C-R
Alkyne
Trans-alkene

Starting materials Catalyst End product

Alkynes Li, Na/ Liquid NH3 Trans-alkene
 Sabatier-Senderen’s Reaction
Catalyst
H2C=CH2 + H2 H3C-CH3 + Heat
Ethene Ethane

Starting materials Catalyst End product

Alkenes Ni, Pt, Pd or Rh Alkanes
 Gabriel Phthalimide Synthesis
N-Ethyl phthalimide
CO CO CO
KOH C2H5X
NH NK NC2H5
∆
CO CO CO
Phthalimide Potassium phthalimide HCl, ∆ 2HOH
COOH
C2H5NH2 +
Ethylamine COOH
Phthalic acid
Starting materials Catalyst End product
Phthalimide KOH; C2H5X; HCl 1o amine
 Diels-Alder reaction
1 1
New Bond
2 2

3 3
Diene New Bond
4 Dienophile 4

Starting materials Catalyst End product

Diene - benzene
 Curtius Rearrangement

Starting materials Catalyst End product

Acyl azide ROH; H2O; R’NH2 1o amine,
Carbamate,
Urea
 Perkin Reaction
O O
Base
Ar O + O Ar OH + HO
Aromatic R R R R
aldehyde Acid anhydride α,β-unsaturated
O O
aromatic acid
Starting materials Catalyst End product
Aromatic HCOONa or HCOOK α, β- unsaturated
aldehyde aromatic acid
 Etard Reaction
CCl4 H2O
C6H5CH3 + 2CrO2Cl2 or CS2 C6H5CH3.2CrO2Cl2 Hydrolysis C6H5CHO
Toluene Brown addition Benzaldehyde
product

Starting materials Catalyst End product

Toluene CCl4 or CS2 Benzaldehyde
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