IMPORTANT ORGANIC COMPOUNDS

COMPOUND FORMULA COMMON MAME IUPAC NAME

HALO COMPOUNDS CH3 -Cl Methyl chloride Chloromethane
R-X CH3-CH2-Cl Ethyl chloride Chloroethane
CH3-CH2-CH2-Cl n-Propyl chloride 1-Chloropropane
(CH3)2 -CH-Cl Isopropyl chloride 2-Chloropropane
CH3-CH2- CH2 -CH2-Cl n-Butyl chloride 1-Chlorobutane
(CH3)2 -CH- CH2Cl Isobutyl chloride 1-Chloro-2-methylpropane
CH3-CH2- CH(Cl) –CH3 sec-Butyl chloride 2-Chlorobutane
(CH3)3 –C-Cl ter-Butyl chloride 2-Chloro-2-methylpropane
C6H5 –Cl Phenyl chloride Chlorobenzene

C6H5 - CH2-Cl Benzyl chloride Benzyl chloride

C6H11Cl Cyclohexyl chloride

ALCOHOLS CH3 -OH Methyl alcohol Methanol

R-OH CH3-CH2-OH Ethyl alcohol Ethanol
CH3-CH2-CH2-OH n-Propyl alcohol Propan-1-ol
(CH3)2 -CH-OH Isopropyl alcohol Propan-2-ol
CH3-CH2- CH2 -CH2-OH n-Butyl alcohol Butan-1-ol
(CH3)2 -CH- CH2OH Isobutyl alcohol 2-Methyl propan-1-ol
CH3-CH2- CH(OH) –CH3 sec-Butyl alcohol Butan-2-ol
(CH3)3 –C-OH tert-Butyl alcohol 2-Methylpropan-2-ol
C6H5 -OH Phenol Phenol
C6H5 - CH2-OH Benzyl alcohol Benzyl alcohol
CH2 = CHOH Vinyl alcohol Ethen- 1-ol

ETHERS CH3 –O - CH3 Dimethyl ether Methoxymethane

R-O-R’ CH3-CH2-O – CH2-CH3 Diethyl ether Ethoxy ethane
C6H5 - O- CH3 Anisole Methoxybenzene

ALDEHYDES HCHO Formaldehyde Methanal

R- CHO CH3 -CHO Acetaldehyde Ethanal
CH3-CH2-CHO Propionaldehyde Propanal
CH3-CH2-CH2-CHO Butyraldehyde Butanal
C6H5 -CHO Benzaldehyde Benzaldehyde

KETONES CH3 –CO - CH3 Acetone Propanone

R-CO - R’ C6H5 –CO - CH3 Methyl phenyl ketone Acetophenone
C6H5 –CO - C6H5 Diphenyl ketone Benzophenone

CARBOXYLIC ACIDS HCOOH Formic acid Methanoic acid

RCOOH CH3 -COOH Acetic acid Ethanoic acid
CH3-CH2-COOH Propionic acid Propanoic acid
C6H5 –COOH Benzoic acid Benzoic acid
ACID DERIVATIVES
ACID CHLORIDES CH3 –COCl Acetyl chloride Ethanoyl chloride
C6H5 –COCl Benzoyl chloride Benzoyl chloride

AMIDES CH3 –CONH2 Acetamide Ethanamide

C6H5 -CONH2 Benzamide Benzamide

ESTERS CH3 -COO CH2-CH3 Ethyl acetate Ethyl ethanoate

AMINES Primary amines

RNH2 CH3 - NH2 Methyl amine Methanamine
CH3-CH2- NH2 Ethylamine Ethanamine
CH3-CH2-CH2- NH2 n-Propylamine Propan-1-amine
C6H5 - NH2 Aniline Benzenamine/Aniline
Secondary amines
Dimethyl amine N-Methylmethanamine
(CH3)2 -NH
Tertiary amines
Trimethyl amine N,N-Dimethylmethanamine
(CH3)3 -N

NITRILES CH3 - C N Methyl cyanide Ethane nitrile

RCN CH3-CH2-CN Ethyl cyanide Propane nitrile
Phenyl cyanide Benzene nitrile
C6H5 -CN

NITRO CH3-CH2- NO2 Nitroethane

COMPOUNDS C6H5 -NO2 Nitrobenzene
RNO2

ISONITRILES CH3 - NC Methyl isocyanide Methyl carbylamines

RNC CH3-CH2-NC Ethyl isocyanide Ehtyl carbylamines
Phenyl isocyanide Phenyl carbylamine
C6H5 -NC
 NAME REACTIONS

1. Wurtz reaction
Alkyl halides react with sodium in dry ether to give hydrocarbons containing double the
number of carbon atoms present in the halide.

2 RX+ 2 Na R-R +2 NaX

2. Wurtz-Fittig reaction
A mixture of an alkyl halide and aryl halide gives an alkylarene when treated with sodium
in dry ether.

3. Fittig reaction
Aryl halides when treated with sodium in dry ether give diphenyl.

4. Finkelstein reaction
R-X + NaI → R-I + NaX X=Cl, Br

5. Swarts reaction
H3C-Br +AgF → H3C-F + AgBr

6. Kolbe’s reaction
When phenol reacts with sodium hydroxide, phenoxide ion generated undergoes
electrophilic substitution with carbon dioxide and forms salicylic acid.

7. Reimer-Tiemann reaction
On treating phenol with chloroform in the presence of sodium hydroxide, a –CHO group is
introduced at ortho position of benzene ring.

8. Williamson synthesis
An alkyl halide is treated with sodium alkoxide to form ether.

CH3Br + C2H5ONa  CH3 – O - C2H5

9. Rosenmund reduction.

Acyl chloride (acid chloride) is hydrogenated over catalyst, palladium on barium sulphate
to give aldehyde..

10. Clemmensen reduction

Aldehydes and ketones are reduced to alkanes on treatment with zinc- amalgam and
concentrated hydrochloric acid.

CH3 –CHO  CH3 - CH3

11. Wolff-Kishner reduction

Aldehydes and ketones are reduced to alkanes on reaction with hydrazine followed by
heating with potassium hydroxide in ethylene glycol.

CH3 –CO - CH3  CH3 –CH2 - CH3

12. Aldol condensation

Aldehydes and ketones having at least one α-hydrogen undergo a reaction in the presence
of dilute alkali form β-hydroxy aldehydes (aldol) or β-hydroxy ketones (ketol), respectively..
13. Cross aldol condensation: When aldol condensation is carried out between two different
aldehydes and / or ketones, it is called cross aldol condensation.

14.Cannizzaro reaction: Aldehydes which do not have an α-hydrogen atom, undergo self
oxidation and reduction (disproportionation) reaction on heating with concentrated alkali. In
this reaction, one molecule of the aldehyde is reduced to alcohol while another is oxidised to
carboxylic acid salt.

15. Hell-Volhard-Zelinsky reaction

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.
16. Gabriel phthalimide synthesis - Phthalimide on treatment with ethanolic potassium
hydroxide forms potassium salt of phthalimide which on heating with alkyl halide followed
by alkaline hydrolysis produces the corresponding primary amine

17. Hoffmann bromamide degradation reaction

Primary amines can be prepared by treating an amide with bromine in an aqueous or
ethanolic solution of sodium hydroxide.The amine so formed contains one carbon less than
that present in the amide.

18.Sandmeyer’s reaction
Benzene diazonium salt with cuprous chloride or cuprous bromide results in the
replacement of the diazonium group by –Cl or –Br.
 Important reactions

i) Chloroform is slowly oxidised by air in the presence of light to an extremely poisonous

gas, carbonyl chloride, also known as phosgene. It is therefore stored in closed dark coloured
bottles completely filled so that air is kept out.

ii) Phenol is manufactured from the hydrocarbon, cumene (isopropylbenzene)

iii) Carbylamine reaction

Aliphatic and aromatic primary amines on heating with chloroform and ethanolic potassium
hydroxide form isocyanides or carbylamines which are foul smelling substances. Secondary
and tertiary amines do not show this reaction.

iv) Coupling reaction

Benzene diazonium chloride reacts with phenol or aniline to form azo dyes.
 DISTINCTION TESTS

S NAME OF CHEMICAL OBSERVATION PAIRS OF COMPOUNDS THAT CAN BE

NO THE REAGENT DISTINGUISHED
COMPOUND
1 R-X Aqueous NaOH & Precipitate 1) Ethyl chloride & chlorobenzene
AgNO3 solution AgCl – White Ethyl chloride gives white ppt
AgBr – Pale Chlorobenzene does not give ppt.
yellow
AgI – Dark 2) Cyclohexylbromide &bromobenzene
yellow Cyclohexylbromide gives pale yellow ppt
Bromobenzene does not give the test.

3) Benzyl chloride & chlorobenzene

Benzyl chloride gives white ppt
Chlorobenzene does not give ppt.

4) Vinyl iodide & Allyl iodide

Vinyl iodide gives pale yellow ppt.
Allyl iodide does not give the test.

2 R - OH Lucas test – conc 10 – Does not To distinguish primary , sec & ter alcohols
HCl & anh ZnCl2 react. Primary – Methanol, Ethanol, n – alkyl
20 – Forms alcohols / alkan – 1-ol, benzyl alcohol
turbidity after Secondary – Isopropyl alcohol, alkan – 2 – ol
few min Tertiary – ter- buytl alcohol (2- methyl –
30 - Forms propan – 2- ol)
turbidity
immediately

Iodoform test – Yellow ppt of Alcohols with CH3 – CH – group give this
NaOH &I2 iodoform (CHI3) test
Note: When both OH
the alcohols given 1) Ethyl alcohol & methyl alcohol (both are
are primary / sec 10)
apply this test Ethyl alcohol gives yellow ppt
Methyl alcohol does not give this test.
2) Pentan – 2- ol & Pentan – 3- ol (both are 20)
Pentan – 2- ol gives yellow ppt
Pentan – 3- ol does not give this test.

3 Phenol Neutral ferric Violet colour 1) Phenol & ethyl alcohol

chloride Phenol gives violet colour
Ethyl alcohol does not give this test
4 Aldehydes Tollens test – Silver mirror Aldehydes give positive test.
ammoniacal 1. Acetaldehyde (Propanal) & Acetone
AgNO3 , warm (Propanone)
 Acetaldehyde (Propanal) gives Ag mirror
Acetone (Propanone) does not give this
test.

Iodoform test – Yellow ppt of

NaOH &I2 iodoform (CHI3) Ald & ket with CH3CO- give +ve test.
Note: When both 1) Acetaldehyde & benzaldehyde
the compounds Acetaldehyde gives yellow ppt.
given are Benzaldehyde does not give this test.
aldehydes/ ketones 1) Acetaldehyde & formaldehyde
apply this test Acetaldehyde gives yellow ppt.
Formaldehyde does not give this test.
3) 2 – Pentanone & 3 – Pentanone
2 – Pentanone gives yellow ppt.
3 – Pentanone does not give this test.
4) Acetophenone & benzophenone
Acetophenone gives yellow ppt.
Benzophenone does not give this test.

5. Carboxylic Sodium Effervescence All carboxylic acids give this test

acids bicarbonate test due to evolution
of CO2 gas

Formic acid Tollens test Effervescence HCOOH is the only carboxylic acid that
( Methanoic due to evolution gives this test
acid) of CO2 gas HCOOH and CH3COOH
HCOOH gives this test . CH3COOH does not
give this test
6 Amines Hinsberg test – 10 –Soluble To distinguish primary , sec & ter amines
Benzene sulphonyl 20 – Insoluble Alkyl amine – 10
chloride + NaOH 30 – does not Dialkylamine -20 (N- alkyl alkanamine)
react with Trialkylamine( N,N – dialkyl alkanamine - 30
Hinsberg reagent

Primary Carbylamine test – Very unpleasant To distinguish primary amines from other
amines Alcoholic KOH + smelling amines
CHCl3 isocyanide gas 1)Ethylamine & Diethylamine
evolves Ethylamine gives this test.
Diethylamine does not give this test
2) Aniline & Dimethylamine
Aniline gives this test.
Diethylamine does not give this test
Aniline Azodye test – Reddish orange
NaNO2 + HCl + dye Aniline & Benzylamine
phenol ( 00 to 5 0 Aniline gives this test
C) Benzylamine does not give this test.