NAMAE RACTION IN ORGANIC CHEMISTRY
(1) Sandmeyer’s reaction
(The reaction was discovered in 1884 by Swiss chemist Traugott Sandmeyer)
(a) Primary aromatic amine, dissolved or suspended in cold aqueous mineral acid, is
treated with sodium nitrite, a diazonium salt is formed
(b) Mixing the solution of freshly prepared diazonium salt with cuprous chloride or
cuprous bromide results in the replacement of the diazonium group by –Cl or –Br.
(2) Finkelstein reaction ( By Hans Finkelstein)
Alkyl iodides are often prepared by the reaction of alkyl chlorides/ bromides with NaI
in dry acetone. This reaction is known as Finkelstein reaction.
(3) Swarts reaction. (
The process was initially described by Frédéric Jean Edmond Swarts in
1892)
The synthesis of alkyl fluorides by heating an alkyl chloride/bromide in the
presence of a metallic fluoride such as AgF, Hg2F2, CoF2 or SbF3. The
reaction is termed as Swarts reaction
(4) Wurtz reaction (named after Charles Adolphe Wurtz)
Alkyl halides react with sodium in dry ether to give hydrocarbons
containing double the number of carbon atoms present in the halide
(5) Wurtz-Fittig reaction (Wilhelm Rudolph Fittig)
A mixture of an alkyl halide and aryl halide gives an alkylarene when
treated with sodium in dry ether and is called Wurtz-Fittig reaction
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6. Fittig reaction (Wilhelm Rudolph Fittig)
Aryl halides give analogous compounds when treated with sodium
in dry ether, in which two aryl groups are joined together. It is called Fittig
reaction.
7. Friedal craft alkylation :- The Friedel–Crafts reactions are a set of
reactions developed by Charles Friedel and James Crafts in 1877 to attach
substituents to an aromatic ring
Friedel–Crafts alkylation involves the alkylation of an aromatic ring with an
alkyl halide using a strong Lewis acid, such as aluminium chloride, ferric
chloride.
8. Friedal Craft Acylation
The electrophilic aromatic substitution allows the synthesis of
monoacylated products from the reaction between arenes and acyl
chlorides or anhydrides
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9. Kolbe’s reaction (named after Hermann Kolbe)
Phenoxide ion generated by treating phenol with sodium hydroxide , it undergoes electrophilic
substitution with carbon dioxide,. Ortho hydroxybenzoic acid is formed as the main reaction
product.
10. Reimer-Tiemann reaction (The reaction was discovered by Karl
Reimer and Ferdinand Tieman)
On treating phenol with chloroform in the presence of sodium hydroxide,
a –CHO group is introduced at ortho position of benzene ring. This
reaction is known as Reimer - Tiemann reaction.
11. Williamson synthesis (This reaction was developed by Alexander
Williamson in 1850)
An alkyl halide is allowed to react with sodium alkoxide to give
symmetrical or unsymmetrial ether.
12. Stephen Reaction :- invented by Henry Stephen
Nitriles are reduced to corresponding imine with stannous chloride in the
presence of hydrochloric acid, which on hydrolysis give corresponding
aldehyde
13.Rosenmund Rreaction :- (The reaction was named after Karl Wilhelm
Rosenmund, who first reported it in 1918)
“-Acyl chloride (acid chloride) is hydrogenated over catalyst, palladium
on barium sulphate. This reaction is called Rosenmund reduction.”
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14. Etard Reduction :- (It is named for the French chemist Alexandre Léon
Étard)
(a) Strong oxidising agents oxidise toluene and its derivatives to benzoic
acids
(b) Use of chromyl chloride (CrO2Cl2): Chromyl chloride oxidises methyl
group to a chromium complex, which on hydrolysis gives corresponding
benzaldehyde.
15. Gatterman Koch Reaction:- (named after the German chemists Ludwig
Gattermann and Julius Arnold Koch)
When benzene or its derivative is treated with carbon monoxide and
hydrogen chloride in the presence of anhydrous aluminium chloride or
cuprous chloride, it gives benzaldehyde or substituted benzaldehyde.
16.Clemmensen Reduction (his reaction is named after Erik Christian
Clemmensen, a Danish chemist)
“The carbonyl group of aldehydesn and ketones is reduced to CH2 group
on treatment with zinc amalgam and concentrated hydrochloric acid
Clemmensen reduction.
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17. Wolff Kishner Reduction:- (reported by Nikolai Kischner in 1911[1] and
Ludwig Wolff in 1912)
“The carbonyl group of aldehydes and ketones is reduced to CH2 group on
treatment with hydrazine followed by heating with sodium or potassium
hydroxide in high boiling solvent such as ethylene glycol”
18. Aldol Condensation :- Aldehydes and ketones having at least one α-
hydrogen undergo a reaction in the presence of dilute alkali as catalyst to
form β-hydroxy aldehydes (aldol) or β-hydroxy ketones (ketol),
respectively. This is known as Aldol reaction.
19. Cannizaro Reaction:- (named after its discoverer Stanislao
Cannizzaro,)
“Aldehydes which do not have an α-hydrogen atom, undergo self
oxidation and reduction (disproportionation) reaction on treatment with
concentrated alkali. In this reaction, one molecule of the aldehyde is
reduced to alcohol while another is oxidised to carboxylic acid salt.
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20. Hell-Volhard-Zelinsky reaction (The reaction is named after three
chemists, the German chemists Carl Magnus von Hell (1849–1926) and
Jacob Volhard (1834–1910) and the Russian chemist Nikolay Zelinsky.
“Carboxylic acids having an α-hydrogen are halogenated at the α-position
on treatment with chlorine or bromine in the presence of small amount of
red phosphorus to give α-halocarboxylic acids. The reaction is known as
Hell-Volhard-Zelinsky reaction.”
21. Carbylamine test: When a primary amine is heated with alcoholic
caustic potash and chloroform, an offensive smelling compound called
carbylamine ( alkyl or arylisocyanide) is formed.
22. Gabriel phthalimide synthesis
This method is used to prepare primary amine. The various steps involved
are:
i) pthalimide is treated with alcoholic solution of KOH to form potassium
pthalimide.
ii) The potassium salt is treated with an alkylhalide.
iii) The product N-alkyl phthalimide is hydrolysed with dilute HCl to form a
primary amine.
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23. Hoffmann bromamide degradation reaction (he reaction is named
after its discoverer – August Wilhelm von Hofmann)
1. When an amide is heated with bromine and an alkali, a primary amine
containing one carbon less than the amide is obtained. This reaction is
called Hoffmann-Bromamide reaction.
2. This reaction is very useful for converting a higher homologue to next
lower one.
24. Coupling Reaction
The reaction in which a diazonium salt condenses with an aromatic
compound having an electron rich group eg, aniline, phenol or their
derivatives to form an azo compound (Ar-N=N-Ar) is termed as coupling
reaction
25. Iodoform test:
The compound containing methyl group bonded to carbonyl group (CH 3-
CO-) or (CH3-CH.OH-) reacts with aquous NaOH and iodine solution gives
yellow ppt of Iodoform.
26. Saytzeff Rule
“In dehydrohalogenation reactions, the preferred product is that alkene
which has the greater number of alkyl groups attached to the
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doubly bonded carbon atoms.
27.Dehyrohalogenation :-
Dehydrohalogenation is an elimination reaction that eliminates (removes)
a hydrogen halide from a substrate. The reaction is usually associated with
the synthesis of alkenes,
28. Grignard reagent An important class of organo-metallic
compounds discovered by Victor Grignard in 1900 is alkyl magnesium halide,
RMgX, referred as Grignard Reagents
29. Dows Process:- Chlorobenzene is fused with NaOH at 623K and 320
atmospheric pressure. Phenol is obtained by acidification of sodium phenoxide
so produced.
30. Lucas Test:- Lucas Test: Alcohol treated with Lucas reagent. (HCl + ZnCl2)
If turbidity appears immediately --- Tertiary alcohol
If turbidity appears after 5 min --- Secondary alcohol
If turbidity not appears --- Primary alcohol
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31. Hemiacetal: A hemiacetal or a hemiketal is a compound that results from the addition
of an alcohol to an aldehyde or a ketone, respectively. The Greek word hèmi, meaning
half(semi), refers to the fact that a single alcohol has been added to the carbonyl group.
32. Tollen’s
Test:- (Test given by aldehyde only) It was named after its discoverer,
the German chemist Bernhard Tollens
On warming with ammonical silver nitrate solution(Tollen reagent) in alkaline medium,
aldehyde gives silver mirror on the side of test tube.
2 AgNO3 + 2 NaOH → Ag2O (s) + 2 NaNO3 + H2O
Ag2O (s) + 4 NH3 + 2 NaNO3 + H2O → 2 [Ag(NH3)2]NO3 + 2 NaOH
33. Fehling’s test: :- Fehling solution is alkaline solution of copper sulphate
containing sodium potassium tartarate. Aldehydes gives reddish brown
precipitate of. Cu2O with Fehling solution.
1. Fehling solution A is aqueous copper sulphate
2. Fehling solution B is alkaline sodium potassium tartarate (Rochelle salt).
3. These two solutions are mixed in equal amounts before test.
4. On heating an aldehyde with Fehling’s reagent, a reddish brown precipitate is
obtained.
5. Aldehydes are oxidised to corresponding carboxylate anion.
6. Aromatic aldehydes do not respond to this test
34. α,β-Unsaturated carbonyl
compounds refers to organic compounds with the general structure (O=CR)−Cα=Cβ-R.
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35. Hinsberg’s reagent Amine when shaken with benzene sulphonyl chloride-
1. A clear solution in NaOH solution which on acidification gives an insoluble material
indicates primary amine(a) The reaction of benzenesulphonyl chloride with primary amine
yields N-ethylbenzenesulphonyl amide
2. (b)In the reaction with secondary amine, N,N-diethylbenzenesulphonamide is
formed. Since N, N-diethylbenzene sulphonamide does not contain any
hydrogen atom attached to nitrogen atom, it is not acidic and hence insoluble in
alkali.
3. (c) Tertiary amines do not react with benzenesulphonyl chloride
36. Decarboxylation:- Decarboxylation is a chemical reaction that removes a
carboxyl group and releases carbon dioxide (CO2). Usually, decarboxylation
refers to a reaction of carboxylic acids, removing a carbon atom from a carbon
chain.
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