Named Reactions-1

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Wolf-Kishner reduction
The deoxygenation of aldehydes and ketones to
hydrocarbons via the corresponding hydrazones or
semicarbazones under basic conditions is known as the
Wolff-Kishner reduction

CHEMICAL REACTION:

NH2NH2 C2H5ONa,
C O C NNH2 o
200 C
Aldehyde Hydrazone
or
Ketone
CH2 + NH2
Methylene group
(Alkane)

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Bamford Steven reaction


In this reaction, tosylhydrazones (p-toluenesulfonyl
hydrazones) of aliphatic aldehyde or ketone furnish
more substituted alkene when treated with strong base
like NaOMe, NaH, and NaNH2.

CHEMICAL REACTION:
R'
N NH SO2 CH3 NaOMe
+
R -N2, -H
p-toluenesulfonyl hydrazones

R CH CH R'
Alkene
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DCC (Dicyclohexylcarbodiimide)
oxidation of alcohol
Primary and secondary alcohols were efficiently
oxidized to the corresponding Aldehydes and ketones in
a solution of dimethyl sulfoxide (DMSO)
CHEMICAL REACTION:

OH O
DMSO
CH C
2 2
R1 R R1 R
o o
1 or 2 alcohol Ketone or aldehyde

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Michael addition/ 1, 4 addition/


conjugate addition
It can be defined as the nucleophilic addition of
nucleophile to an a, b-unsaturated carbonyl compound,
and belongs to a group of reactions that are considered
very useful in the mild formation of carbon-carbon
bonds.
CHEMICAL REACTION:
O OH
H+
Nu + CH2 CH C R Nu CH2 CH C R
Nucleophile ab-unsaturated 1, 4-addition
compound
Tautamerism

O
Nu CH2 CH2 C R
1, 2-addition product
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Mannich condensation/reaction
The condensation of a CH-activated compound (usually
an aldehyde or ketone) with a primary or secondary
amine (or ammonia) and a non-enolizable aldehyde (or
ketone) to afford aminoalkylated derivatives is known
as the Mannich reaction
CHEMICAL REACTION: R3
R1 H R5
N H + C O + CH C
H O -H2O
R2 R4

R1 H R3 R5
N C C C
R2 H R4 O
Amino alkylated ketone
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Robinson annulation
The term ‘annulation’ stands for ‘building a ring’. In this
reaction, the formation of α, β-unsaturated cyclic
ketones from methyl vinyl ketones and aldehyde or
ketones takes place. Actually this reaction is a
combination of two reactions. One is ‘Michael Addition’
and the other is ‘Aldol Condensation’.
CHEMICAL REACTION:
OMe
OMe

O KOH (cat)
+
Ethanol
O
Methyl
Ketone
vinyl O
ketone a, b-unsaturated cyclic ketones

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Stobbe condensation
The formation of alkylidene succinic acid or their
monoester by the base-mediated condensation of
ketones and Aldehydes with dialkyl succinate is known
as Stobbe condensation
CHEMICAL REACTION:
O
O C 2H 5 O CH2 C
C + C CH2 OC2H5
1. NaOC2H5
CH3 CH3 O
diethyl succinate 2. HCl, H2O
acetone

H 3C H3 C COOC2H5
COOH
C C + C C
H3C COOH
H3 C COOH

Tetranoic acid Tetranoic acid


mono ethyl ester
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Darzen’s glycidic ester synthesis


The base catalyzed condensation between an a-
haloester and aldehyde or ketone gives an a, b-epoxy
containing ester (glycidic ester) is known as darzen
condensation.
CHEMICAL REACTION:
O O
Cl CH2 C OC2H5 + R C R
a-haloester NaOC2H5

O O R
C2H5 O C CH C
Epoxy ester R
(glycidic ester)
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Beckmann rearrangement
Ketoximes on treatment with acid catalyst such as conc.
H2SO4, PCl5, H3PO4, SOCl2 or C6H5SO2Cl etc., undergo
Beckmann rearrangement to form a substituted amide.
This rearrangement is intramolecular and involves 1, 2-
shift.

CHEMICAL REACTION:

H3C O
SOCl2
C NOH H3C C NHCH3
Ether
N-methyl acetamide
H3C
Acetoxime

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Baeyer-Villiger oxidation
Aliphatic ketones undergo oxidation with Caro's acid
(per monosulphuric acid, H2SO4) or per benzoic acid
(C6H5CO3H) or m-chloro perbenzoic acid or per acetic
acid (CH3CO3H) or CF3CO3H, etc., to form esters or their
hydrolyzed products.

CHEMICAL REACTION:

O O
CF3CO3H
R C R' R C O R'
Ketone Ester

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Curtius degradation
The overall reaction which proceeds by the elimination
of nitrogen from acylazide followed by acidic or alkaline
hydrolysis to yield primary amine containing one
carbon less is called Curtius degradation.

CHEMICAL REACTION:
O O O
SOCl2 NaN3
R C OH R C Cl R C N3
Acid Acyl chloride Acylazide

O
-N2 2NaOH
R C N3 R N C O R NH2 + Na2CO3
Acylazide Heat
Primary amine

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Willgerodt rearrangement
It is the conversion of acetophenone to 2
phenylacetamide and phenylacetic acid in the presence
of modified reagents (sulfur, concentrated ammonium
hydroxide and pyridine).
CHEMICAL REACTION:
O

Pyridine
NH4OH/H2O
Acetophenone
OH NH2
+
O O

Phenylacetic acid 2-phenylacetamide

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Pinacol-pinacolone rearrangement
Two molecules of ketones undergo reduction in the
presence of Mg/ Hg to form pinacol. Upon treatment
with mineral acids, pinacol is converted into pinacolone.
(Dehydration and rearrangement)
CHEMICAL REACTION:

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Meerweili-Ponndorf-Verley
(MPV) reduction
Ketones can also be reduced to secondary alcohols with
aluminium isopropoxide in propan-2-ol solution and
this is Meerweili-Ponndorf-Verley (MPV) reduction.

CHEMICAL REACTION:

R R
[(CH3)2CHO]3Al
C O + 2H CH OH
in (CH3)2CHOH
R R
Ketone Secondary alcohol

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Aldol condensation
It is a chemical reaction in which two or more molecules
of same or different carbonyl compounds containing α-
hydrogen atom unite together in the presence of dilute
bases such as NaOH, Ba(OH)2 or K2CO3, etc., to form
compounds called aldols.

CHEMICAL REACTION:
H
H
Dil. NaOH
H3C C O + H CH2CHO H3 C C CH2CHO
or K2CO3
Acetaldehyde Acetaldehyde OH
(Two molecule of ethanal) 3-hydroxy butanal
[Aldol (Acetaldol)]

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Cannizzaro's reactions
Formaldehyde, benzaldehyde and other aldehydes
containing no α-hydrogen atoms on heating with
concentrated alkali solution (50%) undergo
Cannizzaro's reaction

CHEMICAL REACTION:

2HCHO + NaOH HCOONa + CH3OH


Formaldehye (50%) Sodium Methyl
formate alcohol

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Tischenko's reaction
This is a modified form of Cannizzaro's reaction. All
aldehydes with or without α-hydrogen atoms undergo
Cannizzaro's reaction in presence of aluminium
ethoxide. The acid (by oxidation) and the alcohol (by
reduction) formed react together to give the ester.

CHEMICAL REACTION:
(C2H5O)3Al
2CH3CHO [CH3COOH + C2H5OH]
Acetaldehyde

CH3COOC2H5
Ethyl acetate

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Claisen-Schmidt reaction
This condensation reaction (also known as Claisen
reaction) is between an aliphatic aldehyde or ketone
containing a-hydrogen with benzaldehyde in the
presence of dilute alkali to form an α, β-unsaturated
compound.
CHEMICAL REACTION:
NaOH
CH O + H2 HCCHO
Acetaldehyde
Benzaldehyde

CH CHCHO

Cinnamaldehyde

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Schmidt reaction
This is a reaction between a carbonyl compound and
hydrazoic acid in presence of conc. H2SO4 to form alkyl
cyanide and N-alkyl formamide.

CHEMICAL REACTION:
Conc. H2SO4
R CHO + N3H R CN + HCOONHR + N2
Hydrazoic Alkyl N-alkyl formamide
acid cyanide

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Lederer Manase's reaction


When phenol is treated with 40% formaldehyde in
presence of dilute acid or alkali, a mixture of ortho and
para-hydroxy benzyl alcohol is formed.

CHEMICAL REACTION:
OH OH OH
CH2OH
NaOH
+ HCHO +

Phenol o-hydroxy
CH2OH benzyl
alcohol
p-hydroxy
benzyl
alcohol

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Diazotization reaction
Diazotization is a reaction in which ice cooled solution
of an aromatic primary amine (having -NH2 group
directly attached to nucleus) in an inorganic acid reacts
with sodium nitrite solution leading to the formation of
diazonium salts (Diazo reaction).

CHEMICAL REACTION:
N2Cl
NH2

o
0-5 C + 2H2O + NaCl
+ NaNO2 + 2HCl

Aniline Benzene diazonium


chloride

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Stephen's reaction
Aldehydes are obtained by partial reduction of cyanides
with SnCl2 and HCl and then steam distilled

CHEMICAL REACTION:

SnCl2 H+
R C N + 2H R CH NH.HCl
HCl
Alkyl cyanide Imine hydrochloride H2O

R CHO + NH4Cl
Aldehyde

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Finkelstein reaction
The corresponding alkyl bromides or chlorides are
heated with a solution of sodium iodide in acetone or
methanol. This is a convenient method for the
preparation of alkyl iodides.

CHEMICAL REACTION:
Acetone
C2H5Br + NaI C2H5I + NaBr
Ethyl Ethyl
bromide iodide

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Wurtz reaction
An ether solution of an alkyl halide is treated with
sodium which removes the halogen of alkyl halide and
the two alkyl radicals join together to form an alkane.

CHEMICAL REACTION:

Dry ether
CH3 I + 2Na + I CH3 CH3 CH3 + NaI
Methyl Ethane
iodide

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Corey-House synthesis
An alkyl halide is first converted into lithium alkyl which
reacts with cuprous iodide to form lithium dialkyl
cuprate, LiR2Cu. It is then treated with an alkyl halide to
give an alkane.

CHEMICAL REACTION:

(CH3)2CuLi + BrCH2CH3 CH3CH2CH3 + CH3Cu + LiBr


Lithium Ethyl Propane
dimethyl bromide
cuprate

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Friedel-Crafts reaction
Alkyl halides react with benzene in presence of
anhydrous aluminium halides to form a homologue of
benzene.

CHEMICAL REACTION:
OCH3 OCH3 OCH3

Alcl3 CH3
+ CH3Cl +
anhydrous

Toluene 2-methoxy toluene


or o-methyl anisole CH3
(Minor) p-methylanisole
(Major)

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Reimer-Tiemann reaction
Chloroform reacts with phenol when heated in presence
of sodium hydroxide or potassium hydroxide. The
product formed is salicylaldehyde.

CHEMICAL REACTION:
OH OH

o CHO
65 C
+ CHCl3 + 3 NaOH + 3NaCl + 2H2O

Phenol o-hydroxy benzaldehyde


(Salicylaldehyde)

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Bouveault-Blanc reduction
The reducing agent used is sodium and ethanol. The
aldehyde, ketones and esters etc., are reduced by
nascent hydrogen into corresponding alcohols.

CHEMICAL REACTION:

H2/Ni or Na/alcohol
CH3CHO + 2H CH3CH2OH
or LiAlH4 or NaBH4
Ethanal Ethanol

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Williamson's synthesis
Ethers are formed by heating alkyl halides with sodium
or potassium alkoxides or dry silver oxide. The
attacking nucleophile is OR-.

CHEMICAL REACTION:

55 o
C
C2H5ONa + C2H5I C2H5OC2H5 + NaI
Sodium Ethyl Diethyl ether
ethoxide iodide

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Rosenmund's reduction
Acid chlorides can be reduced into aldehydes with
hydrogen in boiling xylene using palladium or platinum
as a catalyst supported on barium sulphate. This
reaction is called Rosenmund's reduction. Ketones
cannot be prepared by this method.

CHEMICAL REACTION:
Pd, BaSO4
R C O + H2 R C O + HCl
(Boiling xylene)
Cl H
Acid chloride Aldehyde

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Wacker process
Both aldehydes and ketones can be prepared by this
method. Alkenes are directly oxidized to their
corresponding aldehydes and ketones by treating with
an acidified aqueous solution of palladium chloride and
cupric chloride in presence of oxygen or air
CHEMICAL REACTION:
CuCl2
CH2 CH2 + PdCl2 + H2O
Ethene
Air or O2

CH3CHO + Pd + 2HCl
Aldehyde
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Clemmensen's reduction
Aldehydes and ketones when reduced with
amalgamated zinc and conc. HCl yields alkanes. This
process is known as Clemmensen reduction.

CHEMICAL REACTION:
O
Zn Hg
CH3 C H + 4H CH3 CH3 + H2O
Conc. HCl
Acetaldehyde Ethane

O
Zn Hg CH3CH2CH3 + H2O
CH3 C CH3 + 4H
Conc. HCl Propane
Acetone

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Hofmann bromamide reaction


or Hofmann degradation
Amides when heated with bromine and caustic soda or
caustic potash solution, yield primary amines
containing one carbon atom less than the amide.
CHEMICAL REACTION:
RCONH2 + Br2 + 4KOH
Acid amide
Heat

R NH2 + 2KBr + K2CO3 + 2H2O


o
1 Amine

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Claisen condensation
Ethyl acetate (two molecules) undergoes Claisen
condensation in presence of sodium ethoxide involving
α-hydrogen atom. Two molecules of ethyl acetate
combine together to form ethyl acetoacetate or
acetoacetic ester (α, β-keto ester).
CHEMICAL REACTION:
CH3COOC2H5 + CH3COOC2H5
Ethyl acetate C2H5ONa

CH3COCH2COOC2H5 + C2H5OH
Ethyl aceto acetate
(Acetoactic ester)

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Hofmann's ammonolysis method


A mixture of amines (primary, secondary and tertiary
amines) along with quaternary compound is formed
when alkyl halide is heated with alcoholic ammonia in a
sealed tube at 100°C.

CHEMICAL REACTION:
C2H5I
C2H5I + NH3 C2H5NH2 (C2H5)2NH
Ethyl (Alc.) Ethyl amine Dithyl amine
iodide (1°) (2°)

C2H5I C2H5I
(C2H5)3N (C2H5)4N
Triethyl amine Tetraethyl
(3°) ammonium chloride

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Mendius reaction
Primary amines can be prepared by reduction of
nitriles. The reduction is done either catalytically with
H2 and Raney Ni or with sodium in alcohol or sodium
amalgam and alcohol or with LiAlH4.

CHEMICAL REACTION:

H2/ Raney Ni
R C N + 4[H] R N + 4[H]
or LIAlH4
Alkyl nitrile 1° Amine

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Hinsberg's method
It involves the treatment of the mixture with benzene
sulphonyl chloride, i.e., Hinsberg's reagent (C6H5SO2Cl).
The solution is then made alkaline with aqueous alkali
to form sodium or potassium salt of monoalkyl benzene
sulphonamide (soluble in alkali).

CHEMICAL REACTION:
C6H5SO2Cl + RNH2 C6H5SO2NHR
-HCl
Benzene 1
o
N-alkyl benzene KOH
sulfonyl Amine sulfonamide
chloride
C6H5SO2N(K)R
Soluble salt
NOTE: When 1˚ amine is replaced with 2˚ amine and later
treated with aqueous alkali further it gives
no reaction.
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Cope reaction
When a 3°-amine oxide containing at least one β-
hydrogen is heated at 150°C, it decomposes to form an
alkene and a derivative of hydroxylamine (Thermal
elimination).
CHEMICAL REACTION:
CH3
CH2 N
CH3 H2O2 or O3
or Caro's
acid O
1°Amine
CH3
CH2 CH2 N
CH3
+ (CH3)2NOH
150°C
Alkene
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Kolbe's method
or Kolbe's electrolysis
Electrolysis of a concentrated aqueous solution of
either sodium or potassium salts of saturated
monocarboxylic acids yields higher alkanes at anode.

CHEMICAL REACTION:

Electroysis
2CH3COOK + 2H2O CH3 CH3 + 2CO2 + KOH
Potassium Ethane
acetate

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Frankland's reaction
The method is similar to Wurtz reaction. The alkyl
halide is heated with zinc in inert solvent, higher alkane
is formed.

CHEMICAL REACTION:

Ether
RX + Zn +XR R R + ZnX2
Alkyl Alkane
halide

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Grignard reagents
Alkyl magnesium halides (RMgX) are called Grignard
reagents. These undergo double decomposition
reactions with water or ammonia or alcohol or amines
having active H atom to give alkane.

CHEMICAL REACTION:

+ OH
H
RMgx + HOH R H + Mg
Grignard Alkane
reagent X

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Retropinacol rearrangement
(Wagner rearrangement)
It is the rearrangement in open chain compounds in
which shifting of C6H5 (Ph-); CH3 and H- takes place to
form more stable carbocation and hence more stable
products.
CHEMICAL REACTION:
CH3
Conc. H2SO4
H3CH2C C CH CH3

CH3 OH , -H2O
3, 3-dimethyl pentan-2-ol
CH3

H3CH2C C C CH3
CH3
2, 3-dimethyl pent-2-ene
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Birch reduction
Reduction of alkynes with lithium or sodium in liquid
NH3 (Birch reduction) yields produces trans-alkene.

CHEMICAL REACTION:

Li, Na/ liq. NH3 R C H


R C C R + H2
Alkyne H C R
Trans-alkene

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Wittig reaction
Conversion of aldehydes and ketones to alkenes with
the help of alkylidene (methylene) triphenyl
phosphorus (Wittig reagent) is known as Wittig
reaction.

CHEMICAL REACTION:
CH3CH O + (C6H5)3P CH2
Acetaldehyde Heat

CH3CH CH2 + (C6H5)3P O


Propene Triphenyl
phosphine oxide

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Peterson reaction
β-Hydroxy alkyl silane gives elimination reaction in
presence of acid as well as base. It is stereoselective of
E- and Z- isomers of alkene.
CHEMICAL REACTION:

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Sabatier-Senderen's reaction
Alkenes combine with hydrogen under pressure and in
presence of a catalyst (Ni, Pt, Pd or Rh) to form
corresponding alkanes.

CHEMICAL REACTION:
Catalyst
CH2 CH2 + H2 CH3 CH3
Ethene Ethane

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Sandmeyer reaction
The most convenient method of preparing
chlorobenzene in laboratory is by Sandmeyer's reaction,
in which benzene diazonium chloride obtained from
aniline is heated with cuprous chloride in presence of
hydrochloric acid.
CHEMICAL REACTION:
NH2 N N+ Cl- Cl

NaNO2, HCl CuX

Aniline Benzene diazonium Chloro benzene


chloride

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Gattermann-Koch synthesis
It is a direct method for introducing an aldehydic group
(-CHO) in benzene. It is called Gattermann-Koch
synthesis when a mixture of dry HCl gas and carbon
monoxide is used in presence of anhydrous aluminium
chloride.
CHEMICAL REACTION:
CHO

Anhy. AlCl3
+ CO +HCl

Benzene Benzaldehyde

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Blance reaction
By heating benzene with formaldehyde solution and HCl
in presence of anhydrous zinc chloride, benzyl chloride
is formed and this reaction is called chloromethylation
or Blance reaction.

CHEMICAL REACTION:
CH2Cl

Anhy. AlCl3
+ HCHO +HCl + H2O

Benzene Benzyl chloride

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Von Richter reaction


When halonitrobenzene is heated with KCN at 150˚C,
the, -NO2 group is expelled and a cyano (or -COOH)
group enters the ring at ortho-position with respect to
nitro group.

CHEMICAL REACTION:

NO2
KCN
C2H5OH
Br Br CN
Halonitrobezene Cyano-halobenzene

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Ullmann biaryl synthesis


Iodobenzene, on heating with copper at 200°C in a
sealed tube, forms biphenyl. The reaction is facilitated if
a strong electron withdrawing group is present in ortho
or para-position

CHEMICAL REACTION:

I + 2Cu + I

Iodobenzene

+ 2CuI

Diphenyl (Biaryl)
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Hunsdiecker's reaction
An alkyl halide is formed when the silver salt of
monocarboxylic acid is heated with halogen.

CHEMICAL REACTION:
COOAg
CCl4
+ Br2

Silver benzoate
Br
+ AgBr + CO2

Bromobenzene
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Raschig method
The vapors of benzene, air and hydrogen chloride are
passed over cupric chloride at about 230°C when
chlorobenzene is obtained in sufficient yield.
CHEMICAL REACTION:
CuCl2
2 + 2HCl + O2

Benzene
Cl
2 + H2O

Chlorobenzene

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Fischer Esterification Reaction


Ethyl acetate is prepared by refluxing a mixture of
absolute alcohol and glacial acetic acid in presence of a
few drops of conc. sulphuric acid (catalyst) or hydrogen
chloride gas.

CHEMICAL REACTION:

Conc. H2SO4
CH3COOH + C2H5OH CH3COOC2H5 + H2O
Acetic acid Ethyl Ethyl acetate
alcohol

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Gabriel Phthalimide Synthesis


Phthalimide is reacted with ethanolic solution of KOH to
form potassium phthalimide. The potassium salt is
treated with an alkyl halide. The product N-alkyl
phthalimide is put to hydrolysis with dilute hydrochloric
acid under pressure where pure primary amine is
formed.
CHEMICAL REACTION:

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Etard reaction
Chromyl chloride dissolved in CS2 or CCl4 is made to
react with toluene in CS2 when a brown coloured
product is formed. This product is decomposed with
water when benzaldehyde is formed
CHEMICAL REACTION:
CH3 CH3 . 2CrO2Cl2

CCl4 H2O
+ 2CrO2Cl2
or Cs2
(Hydrolysis)
Toluene Brown adition
product CHO

Benzaldehyde
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Perkin reaction
When an aromatic aldehyde is heated with an aliphatic
acid anhydride with atleast two α-H atom in presence of
Na or K salt of corresponding acid, a condensation
reaction giving α, β-unsaturated acid is formed.
CHEMICAL REACTION:
O O
CHO
O Base
+
R R
Aromatic Acid anhydride
aldehyde O O
H
C
HO OH
+
R R
Carboxylic acid a,b-unsaturated
aromatic acid
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Diels-Alder reaction
It is a diene-dienophile addition reaction. It forms cyclic
compounds.

CHEMICAL REACTION:

1 1 New bond
2 2

3 3
New bond
4 4
Dienophile Cyclic adduct
Diene (Ethene)
(Butadiene) (Cyclohexene)

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Woodward reaction
When alkene is treated with iodine and silver acetate, it
will undergo nucleophilic displacement with acetate in
the presence of water. The intermediate product gives
the desired diols on hydrolysis

CHEMICAL REACTION:

H3C CH3 H3C CH3


I2, CH3COOAg C
C C C
CH4 H3C CH3
H3C CH3 CH3 CH3
Alkene Diols

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Balz-Schiemann reaction
It is a chemical reaction in which a primary aromatic
amine is transformed to an aryl fluoride via a diazonium
tetrafluoroborate intermediate.

CHEMICAL REACTION:
NH2 N NBF4 F

NaNO2 / HBF4 + N2 + BF3


273-278K
Aniline Benzene diazonium Fluorobenzne
tetrafluoroborate

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Coupling reaction
Benzene diazonium chloride when reacts with phenol in
alkaline medium it produces p-hydroxyazobenzene
CHEMICAL REACTION:

pH 9-10
N NCl + OH

Phenol 273-278K
Benzene diazonium
chloride

N N OH + HCl

p-hydroxyazobenzene
(Orange dye)

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Wurtz-Fittig reaction
It is the chemical reaction of aryl halides with alkyl
halides and sodium metal in the presence of dry ether to
give substituted aromatic compounds.

CHEMICAL REACTION:

Cl + 2Na + Cl
Dry ether
Chlorobenzene

+ 2NaCl

Diphenyl

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Fries rearrangement
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It is a rearrangement reaction of phenolic ester to a


hydroxy phenyl ethyl ketone in the presence AlCl3.
CHEMICAL REACTION:
O
OH O C C2H5

C2H5COCl
AlCl3
Cs
Phenol Phenol propionate
OH
OH O
C C2H5
p-hydroxy phenyl +
ethyl ketone
(Minor product)
o-hydroxy phenyl
O C C 2H 5 ethyl ketone
(Major product)

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Gattermann reaction
This reaction is used for obtaining chlorobenzene or
bromobenzene from benzenediazonium
chloride/bromide by treating it with Cu/HCl or Cu/HBr
CHEMICAL REACTION:

Cu/HCl
N NCl

Benzenediazonium
chloride

Cl + N2

Chlorobenzene
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Gattermann-aldehyde reaction
This reaction is used for obtaining benzaldehyde from
benzene by treating it with HCN/ HCl in the presence of
AlCl3.
CHEMICAL REACTION:
Anhy. AlCl3
+ HCN + HCl

Benzene

H2 O
CHO CH NH.HCl
Boil
Benzaldehyde Chlorobenzene
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Haloform/ Iodoform reaction


It is used to check the presence of carbonyl compounds
with the structure R-CO-CH3 or alcohol with the
structure R-CH(OH)-CH3 in a given unknown substance.

CHEMICAL REACTION:
OH
CH3CHCH3 + 4I2 + 6NaOH CHI3 + CH3COONa + 5NaI + 5H2O
CH3COCH3 + 4I2 + 6NaOH CHI3 + CH3COONa + 3NaI + 3H2O

Iodoform

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Hell-Vohard Zelinsky reaction


It is the reaction in which halogenation of carboxylic
acid occur having alpha hydrogen result in the
formation of alpha Halo carboxylic acid product in the
presence of phosphorous catalyst.

CHEMICAL REACTION:
Cl2, P Cl2, P
CH3COOH ClCH2COOH
Acetic acid -HCl Mono chloro -HCl
acetic acid

Cl2, P
Cl3CCOOH Cl2CHCOOH
Tri-chloro acetic -HCl Di-chloro acetic

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Hoffmann mustard oil reaction


It is an organic reaction in which primary amines are
warmed with alcoholic carbon disulphide (CS2 ) and
then heated with excess of mercuric chloride (HgCl2 )
leading to the formation of isothiocyanates

CHEMICAL REACTION:
CH3CH2NH2 + S C S
Ethylamine Carbon
disulfide
S
HgCl2
CH3 CH2 N C S CH3 CH2 NH C SH
Dithioethyl carbamic acid
Ethylisothiocyanate

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Kolbe-Schmidt reaction
It is a carboxylation chemical reaction that proceeds by
heating sodium phenoxide with carbon dioxide under
pressure, then treating the product with sulfuric acid.
The final product is an aromatic hydroxy acid which is
also known as salicylic acid
CHEMICAL REACTION:
ONa OH
COONa
+ CO2 4-7atm H+
400 K
H2O
Sodium Sodium salicylate
phenoxide OH
COOH

Salicylic acid
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Libermann Nitroso reaction


This is a test for secondary amines. Secondary amines
(aliphatic as well as aromatic) react with nitrous acid to
form N-nitrosoamines. Where the product obtained is
N-Nitrosodimethyl amine.

CHEMICAL REACTION:

R2NH + OH N O
o
2 amine

R2N N O + H2O
N-nitrosodialkyl
amine
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Oppenauer oxidation
It is the process of conversion of secondary alcohols to
ketones by selective oxidation in the presence of
aluminium tert-butoxide [(CH3)3CO]3Al .

CHEMICAL REACTION:
R
3 CH OH + [(CH3)3CO]3Al
R'
Secondary alcohol

R
3 (CH3)2O R
C O
CH O Al + Me3C OH
R'
R' 3
Ketone

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The Dieckmann
condensation/reaction
It is the intramolecular chemical reaction of diesters
with base to give β-ketoesters

CHEMICAL REACTION:
O O
1. Base O
+
OR 2. H
OR
O
ROH b-ketoester
Diester
OR

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Knoevenagel reaction
A method to prepare a, b-unsaturated monocarboxylic
acid in the presence of organic base.

CHEMICAL REACTION:

Pyridine
RCHO + CH2(COOH)2
Base
Aldehyde

RCH C(COOH)2
ab-mono carboxylic acid

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Reformatsky reaction
It is an organic reaction between a-bromoacid ester and
aldehydes or ketones using metallic zinc to form β-
hydroxy-esters.
CHEMICAL REACTION:
R
R CH COOC2H5 + Zn BrZnCH COOC2H5
Br R'
a-bromo acid ester C O
"R
OH
R' C CH COOC2H5
R" R
b-hydroxy-esters
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Markovnikov way of addition


When an unsymmetrical reagent adds to an
unsymmetrical alkene, the negative part of the reagent
get attached to that carbon atom which is joined to
lesser number of Hydrogen atom.

CHEMICAL REACTION:

Br

CH3CH CH2 HBr CH3CHCH3


No peroxide
Propylene Isopropyl
bromide

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Anti-Markovnikov
way of addition
When any polar molecule is added to any
unsymmetrical alkene in presence of any organic
peroxide, the negative part of molecule is added to that
carbon atom which is connected to more Hydrogen
atom than the other unsaturated carbon atom.

CHEMICAL REACTION:

HBr
CH3CH CH2 CH3CH2CH2Br
Peroxide
Propylene n-propyl
bromide

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Lucas test
Lucas reagent: Conc. HCl and anhydrous ZnCl2.
 When 3˚ alcohol is treated with Lucas reagent
cloudiness appear at once

 When 2˚ alcohol is treated with Lucas reagent


cloudiness appears within 5-minutes.
 When 1˚ alcohol is treated with Lucas reagent
no cloudiness appears at room temperature.

Note: Lower alcohols are soluble in water but their


corresponding alkyl halide is insoluble in water,
which results in cloudiness.

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Victor Meyer test


It is used to differentiate between primary, secondary
and tertiary alcohol by the colour they obtain when
they interact with the victor Meyer reagent.
STEPS:
 The alcohol is treated with iodine in the presence
of red phosphorus to give iodoalkane
 Iodoalkane is allowed to react with alcoholic silver
nitrate to obtain nitro alkane
 The nitro alkane is then treated with nitrous acid and
the solution which resulted is made alkaline
Observation: 1˚ alcohols – Blood Red colour
2˚ alcohols – Blue colour
3˚ alcohol – No colour is observed
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