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N-Ethanamide Synthesis Overview

Name reactions used in +1, +2 organic chemistry

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0% found this document useful (0 votes)
285 views9 pages

N-Ethanamide Synthesis Overview

Name reactions used in +1, +2 organic chemistry

Uploaded by

prof.naval.rana
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as DOCX, PDF, TXT or read online on Scribd

SOME ORGANIC REACTION

1. Acylation :- Replacement of a hydrogen atom bonded to the nitrogen atom of ammonia or an amine or H atom of
C6H6 ringby an acyl group.
CH3CH2NH2 + CH3COCl  CH3CH2NHCOCH3
ethanamine ethanoyl N-ethanamide
chloride
Pyridine
C6H6 + CH3COCl C6H5COCH3
2. Aldol Condensation :- Condensation reaction between two molecules of a carbonyl compound (aldehydes or
ketones) containing - hydrogen atom in the presence of dilute akali. For example, acetaldehyde (ethanal) gives a -
hydroxy aldehyde.
O OH O
  
NaOH
2CH3  C  H CH3  C  CH2  C  H
ethanol 
H
3-hydroxy butanal (Aldol)
3. Alkylation :- Replacement of a hydrogen atom bonded to the nitrogen atom of ammonia or an amine or H atom of
C6H6 ring by an alkyl group. Methylation is replacement by a methyl group.
CH3

OH −
CH3 - CH2 - NH2 + CH3I CH3 - CH2 - NH + H 2O
ethanamine iodomethane N-methyl ethanamine
FeCl 3
C6H6 + CH3Cl C6H5CH3 + HCl
4. Acyloin Condensation :- Acyloin is -hydroxy ketone. Acyloins are produced when aliphatic carboxylic esters
perfectly methyl or ethyl esters are treated with sodium in an inert solvent like ether, benzene or toluene followed by
treatment with acid.
Na + ether
2CH3COOC2H5 CH3 – C – C – CH3 + 2C2H5Ona
 
O O
disketone
2H+
CH3 – C – C – CH3 CH3 – C – CH – CH3
   
O O O OH
(acyolin)
5. Arndt-Eistert Synthesis :- It involves the conversion of carboxylic acid into next higher homologue i.e. RCOOH to
RCH2COOH.
O

PCl 5 CH 2 N 2
R – COOH R – COCl R – C – CHN2
acid chlorine (diazomethane) diazoketone
Ag 2 O H2 O
R – CH = C = O R – CH2COOH
ketene acid
6. Aromatisation :- It involves the conversion of an aliphatic compound into aromatic one.
Catalyst

C6H14 high P & T C6H6 + 4H2


(hexane) (benzene)
7. Bouveaults-Blanc Reduction :- Reduction of esters to primary alcohols by Na/C2H5OH.
Na/C 2 H 5 OH
CH3CH2CH2COOC2H5 CH3CH2CH2CH2OH
ethyl butyrate butanol
8. Balz-Schiemann’s Reaction :- Benzene diazonium chloride on reaction with NaBF4 gives fluorobenzene.

NaBF 4
N2Cl F
benzne diazonium Fluorobenzene
chloride

9. Baeyer’s Test :- Decolorisation of cold, dil and neutral aq. Soln. Of KmnO4 (purple) by unsaturated hydrocarbons
(a test for unsaturation).
CH3 = CH2 + H2O + O HOCH2 – CH2OH
(from KmnO4) glycol
10. Benzoin Condensation :- Two molecules of benzaldehde on condensation in presence of alcohol KCN give
benzoin.
alc . KCN
2C6H5CHO C6H5 – CH – C – C6H5
benzaldehyde  
OH O
(benzoin)
11. Birch Reduction :- It involves the reduction of olefinic bond by sodium in liquid ammonia in presence of a alcohol.
Na/NH3 ( alc. )

RCH = CH2 2[H ] RCH2 – CH3


Benzene can also be reduced by this reaction.

Birch reduction
(1, 4-cyclohexadiene)
12. Baeyer-Villiger Oxidation :- It involves the oxidation of ketones with organic peroxy acid like perbenzoic acid
C6H5CO3H or per acetic acid (CH3CO3H) to form esters.
O O
 Peracetic acid 

CH3 – C – CH3 (CH CO H ) CH3 – C – OCH3


3 3

acetone methyl acetate


13. Brown Hydroboration :- This involves addition of diborane (B2H6) to olefinic double bond to form triorganoborane
which on subsequent treatment with H2O2/OH- gives alcohol. This shows anti Markownikoff’s addition of H 2O across
unsymmetrical C = C bond.
H 2 O2 /O H

6R – CH = CH2 + B2H6 2(R – CH2 – CH2)3B −2H3 BO3 6R – CH2CH2OH


alkene alcohol
14. Benzoylation :- The phenomenon involving replacement of H atom of –OH group, phenolic group, NH 2 group, >NH
group or of –Shgroup by a benzoyl (C6H5CO-) group is known as benzoylation.
OH OOCC6H5

C6H5COCl +

(benzoyl chloride) phenol phenyl benzoate


The benzoylation of phenol and aniline is also called Schauteen-Baumann reaction.
15. Cannizzaro Reaction :- Aldehydes not containing -hydrogen atoms on heating with conc. Caustic solution undergoes
disproportionation i.e. one molecule of aldehyde is oxidized at the cost of the other (which is reduced).
50% NaOH or KOH
HCHO + HCHO HCOOH + CH3OH
(formaldehyde) (formic acid) (methanol)
50% NaOH
C6H5CHO + C6H5CHO C6H5COOH + C6H5CH2OH
(benzaldehyde) (benzoic acid) (benzyl alcohol)
16. Claisen-Schmidt Condensation :- It involves the condensation between benzaldehyde and aliphatic aldehydes
in the presence of dilute alkali. Also known as Claisen reaction.
OH

Dil. NaOH −H 2 O
C6H5CHO + HCH2CHO C6H5CH – CH2 – CHO C6H5CH = CH – CHO
benzaldehyde acetaldehyde (unstable, mixed aldo) cinnamaldehyde
17. Claisen Condensation :- It involves the self-condensation of esters in the presence of alkoxide base to produce -
ketoester.
O O
 
(i ) NaOC2 H 5
(ii ) H3 O+
2CH3COCH2CH3 CH3C CH2COOC2H5 + CH3CH2OH
ethyl acetate ethyl acetoacetate
(acetoacetic ester)
18. Clemmenson Reduction :- Reduction of aldehydes and ketones (or ketones (or reduction of carbonyl group i.e. C
= O) into hydrocarbon by amal gamated zinc in conc. HCl.

Zn−Hg/ HCl
C=O CH2

Zn−Hg/ HCl
O

cyclohexanone cyclohexane
19. Carbylamine Reaction (Isocyanide Test) :- Foul smelling isocyanides are formed on warming primary amines with
chloroform and alcoholic KOH. Due to offensive of isocyanide (carbylamine). The reaction is a test for primary
amines and is also known as isocyanide test.
RCH2NH2 + CHCl3 + 3KOH RCH2NC + 3KCl + 3H2O
(primary amine) alkyl isocyanide
20. Coupling Reaction :- It involves the condensation between the N atom of a diazo group and a carbon atom of a ring
of phenol or aromatic amines. It is an important reaction for the synthesis of azo dyes. The coupling with phenols
takes place in mild alkaline solution while
OH
− amines show coupling in mild acidic solution.
N2Cl + OH 273 K

benzene diazonium phenol


chloride
N=N OH + HCl
p-hydroxy azobezene
(organge-red dye) H
+

N2Cl + NH2 273 K

aniline
N=N NH2 + HCl
p-amino azobezene
(yellow dyn)
21. Corey-House Reaction :- Alkyl halides on treatment with lithium dialkyl copper in presence of ether give rise to the
formation of alkanes with odd number of carbon atoms.
Ether
R2CuLi + RX R - R+ RCu + LiX
Alkane alkyl copper
For example, theLiformation of pentane from ethyl bromide
CuI
C2H5Br ( ether) C2H5Li (C2H5)2 LiCu
ethyl lithium

Ether
(C2H5)2LiCu + CH3CH2CH2Br C2H5CH2CH2CH3 + C2H5Cu + LiBr
n-pentane
22. Curtius Reaction :- It involves the conversion of acid azide
(R – CON3) into primary amine
O H O
  
CH 3 OH NaOH
R – C – N3 R – N – C – OCH3 R – NH2
acid azide 1° amine
Acid azide can be obtained from acid chlorides or esters by treatment with hydrazine (NH2 – NH2)
O O O
  
NH 2− NH 2 HNO 2
R – C – Cl R – C – NH – NH2
R – C – N3
acid azide
23. Decarboxylation :- It involves the removal of CO2 from a carboxylic acid or its sodium salt e.g.,
Soda−lim e
RCOOH R – H + CO2
Soda−lim e
RCOONa R – H + Na2CO3
24. Dehydration
 The process of removal of H2O molecule from a reactant.
 Substances used from dehydration are known as dehydrating agents.
 Different dehydrating agents (conc. H2SO4, Al2O3, P2O5, KHSO4 etc.) are used in different reaction e.g.
(i) Catalytic dehydration :
Al2 O3

350° C CH2 = CH2 + H2 O


CH3CH2OH
250° C CH3CH2OCH2CH3
(ii) Chemical dehydration :
Al2 O 3

350 ° C CH2 = CH2 + H2O


CH3CH2OH
140° C CH3CH2OCH2CH3

KHSO 4
CHOHCHOHCH2OH Δ CH2 = CHCHO + 2H2O
(glycerol) (acrolein)
conc. H 2 SO 4

HCOOH Δ H2O + CO
(formic acid)

COOH
conc. H 2 SO 4

 Δ H2O+ CO
COOH
(oxalic acid)
P 2 O5

CH3CONH2 Δ CH3CN + H2O


(acetamide)
P 2 O5

2CH3COOH Δ (CH3CO)2O + H2O


P 2 O5

CH3CH = NOH Δ CH3CN + H2O


acetaldoxime
dil. H 2 SO 4

CH3CHOHCH2COOH CH3CH = CHCOOH


Δ

unsaturated acid
25. Dehydrogenation :- It involves removal of a H2 molecule from a substrate molecule.
Cu
CH3CH2OH 300 ° C CH3CHO + H2
Cu
CH3CHOHCH3 300 ° C CH3COCH3 + H2
26. Dehydrohalogenation :-
(i) The process of removing a hydrogen halide molecule from a substrate molecule e.g.
NaNH2 or KOH alc .

-HX
CH3CH2X CH2 = CH2
KOH alc .

XCH2 – CH2X -2HX CH  CH


Δ
XCH2CH2COOH CH2 = CHCOOH
-haloacid acrylic acid
Δ
CH3CHCH2COOH CH2CH = CHCOOH

X
The elimination of HX follows Saytzeff rule.
27. Dehalogenation :- It involves removal of halogen from a substrate molecule.
Zn dust
XCH2 – CH2X CH2 = CH2 + ZnX2
Zn dust
CH3 – CHX2 CH2 = CH2 + ZnX2
28. Diazotization :- Process of converting an aromatic primary amine into diazonium salt by treatment with nitrous acid
(NaNO2/HCl) below 5°C.
¿ 5 °C
C6H5NH2 + HONO + HC l C6H5 – N+ = NCl- + 2H2O
aniline nitrous acid benzene diazonium
chloride
29. Darzen’s Reaction :- It involves the reaction of straight chain primary alcohols with thionyl chloride to form chloro
derivative.
Pyridine
ROH + SOCl2 RCl + SO2 + HCl
30. Elb’s Reaction :- It involves the oxidation of phenol by potassium per sulphate to form a mixture of catechol and p-
quinol
OH OH OH
K 2 S2 O 6 OH
OH− +
phenol catechol OH
p-quinol
31. Etard’s Reaction :- It involves the partial oxidation of toluene with chromyl chloride (CrO 2Cl2) solution in CCl4 or CS2. The
product formed is benzaldehyde.

CH3 CH3.2CrO2Cl2 CHO


2CrO2 Cl 2
CCl
H2 O
4

toluene brown complex benzaldehyde


The reaction is carried out to convert terminal carbon atom in the side chain of an arene to aldehyde by acidic
manganese dioxide or by CrO2Cl2 or by NaCl + K2Cr2O7 + H2SO4
32. Elimination Reaction :- A reaction in which two atoms or groups bonded to adjacent carbon atoms are removed and
a double bond is formed between these carbon atoms.
H X
 
CC + B-  C = C  + X- + HB
   
Some important elimination reaction are already explained under the headings dehalogenation, dehydration,
dehydrogenation, dehydrohalogenation.
33. Esterification :- Formation of an ester by dehydration or catalytic agent
H+
CH3COOH + C2H5OH CH3COOC2H5
ethanoic acid ethanol ethyl ethanoate
C6H5COOH + HOCH3 C6H5COOCH3
benzoic acid methanol methyl benzoate
34. Fittig Reaction :- Aryl halides on reaction with metallic sodium (similar to Wurtz and Wurtz-Fitting reaction) gives
diphenyl.
2C6H5Cl + Na C6H5 – C6H5 + 2NaCl
diphenyl
35. Fries Rearrangement :- Phenyl esters on heating with anh. AlCl3 undergo rearrangement at o - & p – position

OCCH3 OH OH
COCH3
+

phenyl acetate COCH3


o- & p-
hydroxyacetophenones
36. Finkelstein Reaction :- Alkyl bromides and chlorides on reaction with KI in acetone produce alkyl iodides.
R – Cl + KI  R – I + KCl
R – Br + KI  R – I + KBr
37. Fehling’s Test :- A red precipitate is obtained on warming aldehydes with Fehling solution (ketones do not give this
test)
Δ
R – CHO + 2Cu(OH)2 + NaOH R – COONa + Cu2O + 3H2O
(red ppt)
38. Friedel-Crafts Reaction :- It involves alkylation or acylation of benzene and its derivatives in the presence of
anhydrous AlCl3 by alkyl halides or acid halides, respectively.
R
AlCl
3

Alkylation : + RCl anhydrous + HCl


COR
AlCl
3

Acylation : + RCOCl anhydrous + HCl

39. Gabriel phthalimide Reaction (primary amine synthesis):- Potassium salt of phathalimide on heating with an alkyl
halide yields N-alkyl phthalimide which hydrolyses to primary amine on heating with HCl or KOH.
CO KOH CO CO
RI
NH NK NR
CO CO CO
phthalimide pot-phthalimide alkyl phthalimide
CO 2H2O COOH
NR Hydrolysis + RNH2
CO COOH
Phthalic acid p-amine
40. Gatternann Reaction :- The reaction involves the preparation of chloro or bromo benzene from benzene diazonium
chloride by treatment with Cu/HCl or Cu/HBr respectively.
N2+Cl- Cu / HCl
Cl
+ N2
chlorobenzene
N2+Cl- Cu/ HBr
Br
+ N2 + HCl
bromobenzene
41. Gattermann-Koch Reaction :- It involves direct introduction of -CHO group in the benzenering i.e., formylation of
benzene ring (a modification of Friedel-Craft’s reaction_. Here, a mixture of CO and HCl gas passed through
benzene containing anhydrous AlCl3 and a small amount of CuCl.
O + HCl HCOCl
AlCl 3 , CuCl methanoyl chloride

C6H6 + HCOCl C6H5CHO


298 K, 70 atm + HCl
benzaldehyde
42. Grignard Reactions :- Reactions shown by Grignard’s reagent (R – Mg – Br) in the synthesis of several organic
compounds including hydrocarbons, alcohols, aldehydes, ketones, acids etc by reaction with suitable compounds.
Dry ether
RX + Mg R – MgX
Grignard reagent
Tetrahydrofuran
C6H5X + Mg C6H5MgX
Grignard reagent can be further converted into a large number of
compounds by proper choice of reagent.
H2 O
RH + Mg(OH)X
alkane
R ' OH
RH + Mg(OR)X
alkane
R ' NH 2
RH + Mg(NHR)X
alkane
(i ) CO2
( ii) H 2 O R – COOH + Mg(OH)X
acid
RMgX + (i ) RCHO

Grigard reagent ( ii) H2 O R2CHOH + Mg(OH)X


sec. alcohol
(i ) R 2 C=O
( ii) H2 O R3COH + Mg(OH)X
tert. alcohol
(i ) RC ≡ N
( ii) H 2 O R2C = O + Mg(OH)X+ NH3
sec. alcohol

(i) RCOO {R '


RH ¿ + Mg(NHR)X
tert. alcohol
43. Hinsberg’s Test :- A rest that distinguishes between p-, s- and t-amines, involves reaction of amine with benzene
sulphonyl chloride (Hinsberg reagent) in aqueous KOH.
p – amine clear solution that forms precipitate on acidification
s-amine insoluble compound which does not acidify
t-amine suspension that clears upon acidification.
44. Hoffmann Bromamides Reaction :- Formation of primary amine with one carbon atom les than the parent amide,
on treatment with Br2 and KOH.
Δ
CH3CONH2 + Br2 + 4KOH CH3NH2 + 2KBr + K2CO3 + 2H2O
45. Hoffmann Mustard oil Reaction :- Mixture of a primary aliphatic amine, CS 2 and mercuric chloride on heating
produces isocyanate having characteristic smell of mustard oil.
S S
 
HgCl2
CH3CH2NH2 + C = S CH3CH2 – NH – C – SH CH3CH2 – N = C = S
carbon disulfide ethyl isocyanate
(mustard oil)
46. Hunsdiecker Reaction :- This reaction involves the formation of alkyl halide by refluxing silver salt of carboxylic acid
with Br2 in CCl4. The reaction is used in descending the series.
CH3CH2COOAg + Br2 CH3CH2Br + AgBr + CO2
(in CCl4)
47. Hoffmann’s Ammonolysis :- It involves the reaction of alkyl halide with NH3 to form a mixture of primary, sec. and
ter. amines along with quaternary ammonium satls.
NH 3 RX RX
RX
RX −HX RNH2 R2NH −HX R3N [R4N]+X- −HX
1°amine 2° amine 3° amine quaternary salt
48. Hydration :- Hydration involves formation of a new compounds by the addition of H2O in a molecule e.g.
BF 3
CH2 = CH2 + H2O CH3CH2OH
dil . H 2 SO4

CH  CH + H2 O Hg
2+
CH3CHO
As above
CH3 – C  CH + H2O CH3COCH2
CH2 = C = O + H2O CH3COOH
(ketene)
CH3CN + H2O CH3CONH2
49. Hell-Volhard-Zelinsky Reaction (or HVZ Reaction) :- Aliphatic carboxylic acids containing -H ato m by halogen to
give -haloacids.
Cl 2 P Cl 2 P Cl 2 ; P

CH3COOH −HCl CH2ClCOOH −HCl Cl2CHCOOH −HCl Cl3CCOOH


acetic acid trichloroacetic acid
Br 2 ,P Br 2 , p

CH3CH2COOH CH3 – CHCOOH


−HBr CH3C(Br)2COOH −HBr
propanoic acid  2, 2-dibromopropane acid
Br
50. Iodoform Test (Haloform Reaction) :- Methyl carbinols (CH3CHOH-)
O

and methyl ketones (CH3C -) on heating with a halogen and excess of alkali (i.e., NaOX) form haloform. Yellow
crystals of iodoform are produced when the halogen is I2.
CH3CH2OH + 4I2 + 6NaOH CHI3 + HCOONa + 5NaI + 5H2O
51. Kolbe’s Electrolysis :- Sodium or potassium salts of carboxylic acids on hydrolysis give hydrocarbons.
Electrolysis
2CH3COONa(aq) C2H6 + 2CO2 + 2NaOH + H2
[Link]
anode cathode
CH2COONa
Electrolyis
2  C2H4 + 2CO2 + 2NaOH + H2
CH2COONa
di-sodium succinate
52. Kolbe Reaction :- A Method for the synthesis of salicylic acid when sodium phenoxide reacts with CO 2 at 4-7 atm
and 400 K. Sdoium phenoxide is obtained when phenol reacts with sodium hydroxide.
OH ONa OH OH
COONa+ COOH
NaOH CO 2 H

sodium phenoxide salicylic acid


53. Lucas Test :- A test that distinguishes between pri., sec. and ter. alcohols. It involves treatment of the alcohol with
Lucas reagent (ZnCl2/HCl). Outcome depends on the reactivity of alcohols with HCl (pri., sec. and ter.) Alkyl chloride
is formed which shows cloudiness by ter-alcohols immediately, by s-alcohols after a few minutes and no cloudiness
by p-alcohols.
R  OH + HCl R – Cl + H2O
(insoluble in
Lucas reagent)
54. Leuckart Reactior :- this reaction involves the formation of primary amine from aldehydes or ketones by the action
of ammonium formate or formamide followed by hydrolysis.
R R R
HOH /H +
C = O + 2HCOONH4  CH – NH – CHO CHNH2 + HCOOH
H H R
Aldehyde 1° amine

R R R
HOH /H +
C = O + 2HCOONH4  CH – NH – CHO CHNH2 + HCOOH
H H H
ketone amm. formate 1° amine

55. Libermann Nitroso Reaction :- Aliphatic and aromatic secondary amines react with nitrous acid (naNO 2 + HCl) to
give yellow coloured oily nitrosoamines.
R R
NH + HONO N – N = O + H 2O
H R
nitrosoamine
The nitrosoamines on warming with a crystal of phenol and few drops of H 2SO give green solution which on further addition
of NaOH changes to deep blue colour. The reaction is used to distinguish secondary amines from primary
56. Molisch Test :- It is rest for carbohydrates where a deep violet ring is formed when 2-3 drops of 1 % alc. Solution of
-naphthol are added to an aq. Solution of carbohydrate followed by careful addition of conc. Sulphuric acid.
57. Mendius Reaction :- The reduction of alkyl or aryl nitriles to primary amines by sodium and alcohol or LiAlH4.
Na/C2 H5 OH

R – CN + 4H or LiAlH4 RCH2NH2
C6H5 – CN + 4H C6H5CH2NH2
58. Meerwein-Ponndrof – Verley Reduction:- It involves the reduction of aldehyde or ketones to alcohols with
aluminium isopropoxide in 2-propanol solution.
R R
3 C = O + [(CH3)2CHO]3Al CHO Al + 3CH3COCH3
R ketone aluminium R 3
isopropoxide
R R
Dil . H 2 SO4

CHO Al HOH 3 CHOH + Al(OH)3


R 3 R
59. Nucleophilic Substitution :- Replacement of an atom or a group by a nucleophile.
R–X + Nu- R – Nu + X-
The order of reactivity of haloalkanes is :
Tertiary > Secondary > Primary
60. Oppenauer Oxidation :- Reverse of Meerwin-Ponndrof reduction. It involves the oxidation of secondary alcohol with
aluminium tertiary butoxide to ketone in presence of acetone.
R – CHOH + [(CH3)3CO]3Al R – CHO + (CH3)3COH
 aluminium  Al
R [Link] R 3
sec. alcohol
R – CHO + 3CH3COCH3 R – C = O + [(CH3)2CHO]3Al
 Al acetone 
R 3 R
ketone

61. Perkins Reaction :- The reaction between aromatic aldehyde and an anhydride of aliphatic acid in the presence of sodium
salt of the same acid gives , -unsaturated acid. E.g., benzaldehyde and acetic anhydride give cinnamic acid.

CHO O CH = CH – COOH

CH3 – C
CH3 COONa

+ O 455 K + CH3COOH
CH3 – C
benzaldehyde  cinnamic acid
C
acetic anhydride
62. Pyrolysis :- Breaking of a larger molecule into smaller ones on heating in presence of suitable catalyst is known as
pyrolysis. If higher hydrocarbons are decomposed, the reaction is known as cracking.
Δ

CH3CH2CH3 Catalyst CH2 = CH2 + CH4


63. Raschig Process :- An industrial process for the formation of chlorobenzene from benzene.
CuCl 2
2C6H6 + 2HCl + O2 2C6H5Cl + 2H2O
(air)
64. Rosenmund’s Reaction :- Acid chlorides are catalytically reduced to aldehydes on passing H2 gas in presence of Pd
catalyst over baSO4. The high reactivity of Pd as a catalyst is reduced by the poisoning nature of baSO4.
Pd−BaSO 4
CH3COCl + H2 CH3CHO + HCl
acetyl chloride acetaldehyde
Pd−BaSO 4
C6H5COCl + H2 C6H5CHO + HCl
benzoyl chloride benzaldehyde
65. Riemer-Tiemann Reaction :- Formation of salicyladehyde (or salicylic acid) by the reaction of phenol with CHCl 3
(or CCl4).
OH OH OH OH OH
NaOH CHCl2 CH CHO
H2 O −H 2 O
+ CHCl3 350 K OH
Phenol salicylaldehyde
66. Rancidification :- Oils and fats on exposure to moist air for a long time lose their taste and develop foul smell due to
hydrolysis to form fatty acids. This is known as rancidification e.g. Pure Ghee during exposure to moist air hydrolyses
to volatile acids.
67. Reformatsky Reaction :- It involves the formation of -hydroxy ester by the reaction of -bromoester with Zn and
aldehydes or ketones
Br ZnBr
 
CH3CHCOOC2H5 + Zn CH3 – CHCOOC2H5

ZnBr R CH3
  
H 3 O+
CH3CHCOOC2H5 + R – C = O R – C – CHCOOC2H5 + Zn(OH)Br
 
R OH
68. Sabatier-Senderens Reduction :- The reduction of unsaturated hydrcarbon to saturated ones by passing H 2 in
presence of Raney nickel (catalyst) at around 500 K.
RaneyNi
CH2 = CH2 + H2 473−573 K CH3 – CH3

ethane ethane
69. Strecker’s Synthesis :- Aldehydes are converted to -amino acids on reaction with sodium cyanide and NH 4Cl
followed by hydrolysis.
+
NaCN H

CH3CHO CH3 - CH – CN H2 O CH3 – CH – COOH


NH 4 Cl

ethana NH2 NH2


-alanine
70. Stephen’s Reduction :- Partial reduction of alkyl or aryl cyanides to aldehydes with a suspension of anhyd. SnCl 2 in
ether saturated with HCl followed by hydrolysis.
SnCl2 + 2HCl SnCl4 + 2[H]
Ether H2 O

CH3 – C  N + 2[H] + HCl 300° K CH3CH = NHHCl boil CH3CHO + NH4Cl


ethanenitrile acetaldimine acetaldehyde
hydrochloride
71. Sandmeyer’s Reaction :- It involves replacement of  N2Cl group by  Cl,  Br or  CN by reaction of benzene
diazonium chloride with CuCl/HCl, CuBr/HBr or CuCN/HCN, respectively

Cl
CuCl/HCl

chlorobenzene

N2+Cl Br
CuBr/HBr + HCl
+ HCl

benzene bromobenzene
diazonium chloride

CN
CuCN/HCN
+ HCl

benzonitrile
72. Schotten Baumann Reaction :- This reaction involves benzoylation of the compounds containing active hydrogen
such as phenols, primary and secondary amines and alcohols, with benzoyl chloride under the influence of aqueous
sodium hydroxide or pyridine.
Base
C6H5NH2 + ClCOC6H5 C6H5NHCOC6H5 + HCl
aniline benzoyl chloride benzanilide
Base
C6H5OH + ClCOC6H5 C6H5OCOC6H5 + HCl
phenol benzoyl chloride phenyl benzoate
Base
C2H5OH + ClCOC6H5 C6H5COOC2H5 + HCl
Ethyl alcohol ethyl benzoat
73. Schiff’s Test :- Aldehydes on reaction with Schiffs reagent (aqueous solution of a dye rosaniline hydrochloride
decolorized by saturating with SO2) restore the pink colour of the dye. Ketones do not undergo this test.
74. Saponification :- The hydrolysis of an ester (usually triglycerides or fats) by an aqueous base
CH2OOCR CH2OH
 
NaOH
CHOOCR CHOH + RCOONa + RCOONa + RCOONa
 
CH2OOCR CH2OH soaps
fat glycerol

75. Simonini Reaction :- It involves the reaction of silver salts of fatty acids with iodine to give esters.
O O
 
2R – C – OAg + I2 R – C – OR + 2CO2 + 2AgI
O O
 
2CH3 – C – OAg + I2  CH – C – OCH3 + 2CO2 + 2AgI
silver acetate methyl acetate
76. Transesterification :- An ester on treatment with an excess of an alcohol (different from which parent ester is made)
in the presence of acids form a new ester
O O
 
H+
CH3 – C – OCH3 + CH3CH2OH CH3 – C – OCH2CH3 + CH3OH
methyl ethanoate ethanol ethyl ethanoate methanol
77. Tollen’s Test :- A shining deposit of silver on the inner wall of test tube occurs when aldehydes are warmed with
Tollens reagent (amm. Silver nitrate)/ Ketones do not give this test.
Δ
R – CHO + 2Ag(NH3)2OH CH3COONH4 + 2Ag + H2O + 3NH3
aldehyde amm. silver nitrate silver
mirror
78. Tischenko Reaction :- Aldehydes on heating with aluminium ethoxide form esters. This is a modified Cannizzaro
reaction.
( C2 H 5 O )3 Al
2CH3CHO CH3COOCH2CH3
acetaldehyde ethyl acetage
(C H O ) Al
2 5 3

2C6H3CHO Δ C6H3COOCH2C6H3
benzaldehyde benzyl benzoate
79. Ulmann Reaction :- Iodobenzene on heating with Cu powder in a sealed tube gives diphenyl.
2C6H5I + 2Cu C6H5 – C6H5 + 2CuO
iodobenzene diphenyl
80. Wolff-Kishner Reduction :- The reduction of aldehydes and ketones to hydrocarbons on heating with hydrazine and
KOH.
NH 2 NH 2 KOH
R – CHO R – CH = NNH2 R – CH3 + N2
aldehyde hydrazone
81. Williamson’s Synthesis :- A method for the synthesis of ethers by the reaction of alkyl halides and alkoxides or
phenoxide.
CH3Br + CH3ONa CH3OCH3 + NaBr
methyl bromide sod. methoxide dimethyl ether
CH3Br + C6H5ONa CH3OC6H3 + NaBr
sod. phenoxide methyl-phenyl ether
82. Wurtz Reaction :- Ethereal solution of alkyl halide with metallic sodium produces alkanes (not suitable for alkanes
with odd number of carbon atoms). Methane can not be produced by this method. Generally bromo or iodo alkanes
are used because of higher reactivity
Na
2RX Ether R – R + 2NaX
83. Wurtz-Fitting Reaction :- Aryl halide and alkyl halide on warming with metallic Na in dry ether give aromatic
hydrocarbons.
C6H5Br + 2Na + BrCH3 C6H5CH3
bromobenzene toluene

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