SOLVING PROBLEMS BASED ON ORGANIC CONVERSIONS IN SUBTLEST WAYS

AND SHORTEST POSSIBLE TIME

INTRODUCTION : Students memorise all organic reactions but unable to rearrange
all these reactions and solve problems based on organic conversions. This is an
effort to systematize and rearrange the organic reactions to solve problems based
on organic conversions.
METHOD:- Organic conversions are classified as:-
A. Aliphatic conversions.
B. Aromatic conversions

(A) ALIPHATIC CONVERSIONS: Aliphatic conversions further classified as

Step-up conversions
(i) By Wurtz reaction:

(ii) Through cyanide:

RX KCN
R CN
(iii) Through GrignardNa reagent:
RX RR
C OH
RX
Mg
RMgX
C O


(iv) Through Alkyne: R

RX HC C Na
H C C R

(b) Step-down conversions

(i) Through carboxylic acid:
CaO
RCOOH NaOH
RH
(ii) By Hofmann bromamide reaction:
2
RCONH 2 Br R NH 2
KOH

KEY FOR CONVERSIONS

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Sl Reagent Group Group In Remark
No Out
1 KMnO4 / H+ -CH2OH -COOH Strong Oxidation (20
alc ketone)
2 LiAlH4 -COOH -CH2OH Strong Reduction
(ketone 20 alc)
3 Cu / 573 K or -CH2OH -CHO Dehydrogenation
CrO3
4 PCl5 or SOCl2 -OH -Cl
5 Cl2 / or Cl2 / -H -Cl Free radical
UV substitution
6 Aq NaOH / KOH -X -OH Nucleophilic
substitution
7 KCN -X -CN Step Up
8 AgCN -X -NC
9 Alcoholic KOH -HX = Dehydrohalogenation
(Stzf)
10 Mg / dry ether Mg R-X R-MgX
11 HBr >=< H, Br Merkovnikov
12 H2 / Pd-BaSO4 -COCl -CHO Rosenmund
Reduction
13 Zn-Hg / HCl >C=O -CH2- Clemmension
Reduction
14 NH3 / -COOH -CONH2 -COOH + NH3
-COONH4
15 Br2 / NaOH or -CONH2 -NH2 Step Down
NaOBr ( Hoffmann)
16 HNO2 or -NH2 -OH HONO
NaNO2/HCl
17 CHCl3 / alc KOH -NH2 -NC Carbyl amine
18 P2O5 -CONH2 -CN Dehydration
19 H3O+ -CN -COOH Hydrolysis
20 OH- -CN -CONH2
21 LiAlH4 -CN -CH2NH2 Reduction
22 Red P / Cl2 -H of -Cl HVZ Reaction
acid
In benzene ring
23 Fe / X2 /dark -H -X Halogination
24 CH3Cl / AlCl3(anhyd) -H -CH3 Friedel Craft
alkylation
25 CH3COCl / -H -COCH3 Friedel Craft
AlCl3(anhyd) acylation
26 Conc.HNO3/con.H2SO4 -H -NO2 Nitration
27 Conc H2SO4 -H -SO3H Sulphonation
28 KMnO4 / H+ -R -COOH Oxidation
29 CrO2Cl2 / H+ -CH3 -CHO Mild oxidation(Etard
Reaction)
30 Sn / HCl or Fe/HCl -NO2 -NH2 Reduction
31 NaOH / 623K / 300 -Cl -OH
atm
32 Zn dust / -OH -H
33 NaNO2 / dil HCl / -NH2 -N2+Cl- Diazo reaction

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 273-278 K
34 CuCl / HCl or -N2+Cl- -Cl Sandmeyer or
Cu/HCl Gattermann
35 CuBr / HBr or -N2+Cl- -Br Sandmeyer or
Cu/HBr Gattermann
36 CuCN / KCN -N2+Cl- -CN Sandmeyer
37 KI -N2+Cl- -I
38 HBF4 / -N2+Cl- -F
39 H3PO2 or CH3CH2OH -N2+Cl- -H
40 H2O / 283 K -N2+Cl- -OH
41 HBF4/ NaNO2, Cu / -N2+Cl- -NO2
42 C6H5-OH -N2+Cl- -N=N-C6H5- Coupling ( p-
OH hydroxy)
43 C6H5-NH2 -N2+Cl- -N=N-C6H5- Coupling ( p-amino)
NH2

Reactions of Grignard Reagent

Any one below + H2O Product

Grignard reagent +

H2O or ROH or RNH2 R-H
H-CHO R-CH2-OH (10 alc)
R-CHO R-CH(OH)-R (20 alc)
R-CO-R R2C(OH)-R (30 alc)
R-MgX
CO2 R-COOH
R-CN R-CO-R
HCOOR Aldehyde
RCOOR Ketone

NB: i) During reaction generally changes take place in the functional group only so
see the functional group very carefully.
ii) Remember structural formula of all the common organic compounds ( with
their IUPAC and common names)
iii) Wurtz Reaction and Aldol Condensation are not included in the table
although they are very important for conversions so study them .
iv) By taking examples practice all the above cases ( from 1 to 43 and
Grignard)
v) Practice only from NCERT book.
vi) Start practicing NOW !

How to use the table? See below.

Example : See no 7 in the table

Directional Properties of groups in benzene ring for electrophilic

substitution

Ortho-para directing group: -R , -OH, -NH2, -X, -OR, -NHR, -NR2,

-NHCOCH3, -CH2Cl, -SH, - Ph

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Meta-directing group: -NO2 , -CHO , -COOH , COOR , -CN , -SO3H ,
-COCH3 , -CCl3 , -NH3+ ,

(C) Conversions of same no. of carbon atoms

(B) Aromatic Conversions

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CONCLUSION:-
Now students are able to solve the problems based on organic conversions by
using this method in shortest possible time. They can also solve the problems of
what happens when? Complete the reactions etc, which cover the major aspect of
organic chemistry. These conversion charts make organic chemistry interesting for
the students. Teacher can also use it as a teaching aid.
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ASSIGNMENT FOR CLASS XII Sc (CHEMISTRY) ORGANIC CONVERSION---(2 to 3

marks)
CONVERT THE FOLLOWING:-
Q.I# Aniline to (a) benzoic acid (b) benzonitrile (c)
iodobenzene (d)phenol (e) acetanilide
(f) p-nitroaniline (g) sulphanilic acid
Q.II# Benzonitrile to (a)actophenone (b) benzoic acid (c) benzamide
(d) 1-phenyl methanamine (e) aniline
Q.III# Phenol to (a) salicylic acid (b) salicylaldehyde (c) toluene (d)
acetophenone (e) aspirin
Q.IV# Acetylene to (a) Lactic acid (b) Acetaldehyde (c) Acetic acid

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Q.V# Benzaldehyde to (a) -hydroxy phenyl acetic acid (b) Benzophenone (c)
3-phenylpropan-1-ol (d) Benzyl alcohol
Q.VI# Hept-1-ene to (a) Heptanal (b) Hexanal (c) Hexanoic acid
(d) Heptanoic acid .
Q.VII # Acetaldehyde to (a) butan-2-one (b) but-1,3-diol (c) but-2-enal (d)
butan-1-ol (e) butanoic acid (f) but-2-enoic acid (g) Lactic acid (h)
nitropropene -1
Q.VIII # Benzene to (a) m-nitrobenzoic acid (b) phenyl acetic acid (c) p-nitro
benzaldehyde (d) p-nitro benzoic acid (e) methyl benzoate (f) meta-
nitroacetophenone

Q.IX (a) Benzoic acid from chlorobenzene

(b) t-butyl alcohol from acetone
(c) ethanol to propan-2-ol
(d) Methyl cyanide to propanone-2
(e) Acetophenone to 2-phenyl-2-butanol
(f) Methanal to propan-1-ol
(g) bromobenzene to 1-phenyl ethanol
(h) Propanal to Butanone
Q.X # (1) Ethyl amine from acetaldehyde
(2 ) Ethanoyl chloride to methyl nitrile
(3) 2-nitropropane to acetone
(4) Hexanamide to hexanitrile
(5) Propene to acetone and vice versa
(6) Toluene to benzaldehyde
(7) Ethylbromide to ethylamine
(8) Anisole to p-methoxy acetophenone
(9) Benzoyl chloride to benzonitrile
(10) n-propyl alcohol to hexane.
(11) Hexanoic acid to hexanenitrile
(12) p-nitrobenzoic acid to p-nitroaniline
(13) benzoic acid to benzyl amine
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(14) Benzyl alcohol to phenylethanoic acid
(15) m-nitroaniline from nitrobenzene
(16) p-toludine to 2-bromo-4-methyl aniline
(17) Ethanol to 1,2-ethanediol
(18) Acetic acid to acetaldehyde
(19) Acetic acid to ethylamine
(20) acetic acid to acetone
(21) Benzyl alcohol to Benzoic acid
(22) Propanoic acid to Propenoic acid
(23) Cyclohexene to Hexane-1,6-dioic acid
(24) p-methyl acetophenone to benzene-1,4-dicarboxylic acid
(25) Propanoyl chloride to Dipropyl amine
(26) Benzoic acid to Benzaldehyde
(27) Acetophenone to ethyl benzene
Q.XI# (a) Methyl amine to Ethyl amine and vice versa (b) propanoic acid to ethyl ammine (c)
ethyl bromide to propanamine (d) Acetyl chloride to methyl chloride.
IDENTIFY THE COMPOUNDS A,B,C etc.
1# An organic compound A which has characteristic odour, on treatment with
NaOH forms two compounds B and C .Compound B has a molecular formula
C7H8O which on oxidation gives back compound A.
Compound C is the sodium salt of an acid .C when heated with sodalime yields
an aromatic hydrocarbonD.Deduce the structure A,B,C,D .
2# An organic compound A has a molecular formula C 5H10O.It does not reduce
Fehlings Solution but forms a bisulphite compound .It also positive iodoform
test.What is the possible structure of A? Explain your reasoning which helped to
arrive at the structure.
3# A compound A has a molecular formula C5H10O gave a positive 2,4-DNP
testbut a negative Tollens test.
It was oxidized to carboxylic acid B with molecular formula C 3H6O2 when
treated with alkaline KMnO4 under vigorous condition .Sodium salt of B gave a
hydrocarbon C on Kolbes electrolytic reduction Identify A,B and C and write
chemical equations for the reaction.

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4# An organic compound A has a molecular formula C 3H7O2N on reaction with Fe
and Conc.HCl give a compound B of molecular formula C 3H9N . Compound B on
treatment with NaNO2 and HCl give another compound C of molecular formula
C3H8O.The compound C gives effervescence with Na. On oxidation with CrO 3, the
compound C gives a saturated aldehyde containing three carbon atoms .Deduce
the structures of A, B and C and write the chemical equations for the
reactions involved.
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