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Organic Chem New
Organic Chem New
Homocyclic Hetercyclic
Unsaturated compound Saturated C C C O
compound
H2C CH2 + H2 CH3 — CH3
Alkane = Parafin C C C C
CnH2n+2
Chain contains Chain is made up of C and
Alkene Alkyne Para + affinis only C. other atoms
CnH2n CnH2n-2 little reactive
C C C C
Homocyclic Heterocyclic
I.U.P.A.C Nomenclature :
Sec - Prefix + Pri. Prefix + Word root + Pri.suffix + Sec.suffix
Side chain Used to No. of. C atoms Nature of C chain Functional group
alkyl group differentiate present in the (saturated/Unsaturated)
substituent cyclic comp. compound ane/ene/yne
from acyclic
one
Word root: it indicate the no of C- atom present in an organic compound
No of Carbon Word Root
1 Meth
2 Eth
3 Prop
4 But
5 Pent
6 Hex
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7 Sept
8 Oct
9 Non
10 Dec
11 Unidec
12 Dodec
13 Tridec
Primary suffix: this part of organic compound is used to indicate the nature of carbon chain
Secondary suffix: secondary suffix is used to indicate the presence of functional group
O Ketone one
C
Butyl
H2C CH2
Example: cyclobutyle
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Secondary prefix: it is used to indicate the side chain (alkyl group) or some functional groups like
florine, chlorine, bromine, iodine,
F ,
Cyclopropyl
Phenyl
n- Alkane:
It is used when all the carbon atoms are present in straight chain
n-Butane n-Pentane
n-Hexane n-Heptane
Iso – alkane: when one methyl is present in the second carbon.
Note: Start from 4- carbon
CH3 CH3
Iso-butane
Iso-pentane
CH3
CH3
Iso-hexane
Iso-nonane
Note:
CH3 CH3 CH3
Alkyl group: When one hydrogen atom is removed from alkane, the remaining part is called alkyl
group.
Alkyl group general formula:
Alkane →
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H H H H H H
H—C—H —H —H
H—C— H—C—C—H H—C—C—
H H H H H H
Methane Methyl Ethane Ethyl
OH
Types of alkyl group obtained from saturated hydrocarbon:
n-alkyl: If hydrogen is removed from n- alkane, , we get n- alkyl
Note: it is used from 3-C atoms
n- alkane →
Example:
1° 2° 1° 1° 2° 2° 1°
CH3 — CH2 — CH3 CH3 — CH2 — CH2 — CH3 — CH2 — CH2 — CH3 CH3 — CH2 — CH2 — CH2 —
n-propane n-propyl n-butane n-butyl
Secondary alkyl: it is obtained from n- alkane, when from 2nd carbon, is removed
n-alkane→
1° 2° 1° 2° 2° 1°
1°
CH3 — CH2 — CH3 CH3 — CH — CH3 CH3 — CH2 — CH2 — CH3 CH3 — CH2 — CH — CH3
n-propane sec-propyl or iso-propyl n-butane sec-butyl
1° 2° 2° 2° 1°
CH3 — CH2 — CH2 — CH2 — CH3 CH3 — CH2 — CH2 — CH — CH3
n-pantane sec-pentyl
1° 2° 2° 2° 2° 1°
CH3 — CH2 — CH2 — CH2 — CH2 — CH3 CH3 — CH2— CH2 — CH2 — CH — CH3
n-hexane sec-hexyl
OH NH2
CH3 — CH — CH3 CH3 — CH — CH3
sec-propyl alcohol sec-propyl amine
or iso-propyl alcohol or iso-propyl amine
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OH NH2
CH3 — CH2 — CH2 — CH — CH3 CH3 — CH2 — CH2 — CH — CH3
sec-pentyl alcohol sec-pentyl amine
OH NH2
CH3 — CH2— CH2 — CH2 — CH — CH3 CH3 — CH2— CH2 — CH2 — CH — CH3
sec-hexyl alcohol sec-hexyl amine
Tertiary alkyl group: this group is obtained when is removed from iso- alkane
1° CH3 CH3
CH3 CH3 1° 3° 2° 1°
1° 3° 1° CH3 CH CH2 CH3 CH3 C CH2 CH3
CH3 CH CH3 CH3 C CH3
Iso-pentane
Iso-butane
tert-pentyl
tert-butyl (t.Bu)
CH3 CH3
CH3 — CH2 — CH2 — CH — CH3 CH3 — CH2 — CH2 — C — CH3
3°
iso-hexane tert.hexyl
CH3 CH3
CH3 — C — CH3 CH3 — CH2 — C — CH3
OH OH
tert.butyl alcohol tert.pentyl alcohol
CH3
CH3 — CH2 — CH2 — C — CH3
tert.hexyl alcohol OH
Iso- alkyl: this group is obtained when is removed from iso- alkane.
→
CH3 CH3 CH3 CH3
CH3 — CH — H CH3 — CH —
iso-propane iso-propyl
Iso-butane Iso-butyl (sec. butyl)
CH3 CH3
10 10 10
CH3 — CH — CH2 — CH3 CH3 — CH — CH2 — CH2
X iso-pantane iso-pantyl or 3 methyl butyl
Note: for iso-alkyl, methyl group should be present at 2nd last carbon and hydrogen have to remove from 10 carbon
CH3 CH3
CH3 — CH — OH CH3 — CH — NH2
iso-propyl alcohol iso-propyl amine
CH3 CH3
10 10
CH3 — CH — CH2 — CH2 — Cl CH3 — CH — CH2 — Cl
iso-pantyl chloride or 3 methyl iso-butyl chloride
butyl chloride
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Neo- alkyl: this group is obtained when is removed from neo- alkane.
CH3 C CH3 CH3 C CH2 CH3 C CH2 CH3 CH3 C CH2 CH2
CH3 CH3
CH3 CH3
neo-heptane neo-heptyl
CH3 CH3
10 10
CH3 — C — CH2 — CH2 — CH2 — Cl CH3 — C — CH2 — CH2 — Cl
CH3 CH3
neo-heptyl chloride neo-hexyl chloride
CH3
10
CH3 — C — CH2 — Cl
CH3
neo-pentyl chloride
Iso- alkyl : it is obtained from iso- alkane when Neo- alkyl: it is obtained from neo- alkane, when
is removed from iso- alkane. is removed from neo- alkane.
Note: for iso-alkyl, methyl group should be
present at 2nd last carbon and hydrogen have to
remove from 10 carbon.
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b) If two chains having equal no of C. atom are there then select the chain in which maximum no of
side chains are present as the parent chain.
C C Side chain
Side chain
C C C C C C C C
Parent chain(8C)
C
C
Side chain
C
c) If two chains of equal no. of carbon in parent chain and with equal no. of side chains is possible
then select the chain in which side chain is present at lowest position as the parent chain.
Side chain
4 ' '
3 5 4 3' 2 '
1 2 1
6 Side chain
7
× 8
9
10
11
12
Parent chain
1 2 3 4 5 6 7 8 9 10 11 12
Side chain = 2 Right
1' 2' 3' 4' 5 6 7 8 9 10 11 12
Side chain = 2
d) If two side chains are present at equal position from both ends for the selection of parent chain
then alphabetical order is used for the selection of parent chain
7 6 5 4 3 2 1
C C C C C C C Parent chain
CH3 C2H5
Side chain
3 - ethyl - 5 - methylbutane
e) After the selection of parent chains numbering is done in parent chain in such a way that side-
chain get minimum no. this rule is called lowest locant rule. In old system of IUPAC
nomenclature, lowest sum of locant rule was applied but now- a- days, only longest locant rule is
applicable.
1 2 3 4 5 6 7 8 9 10
C C C C C C C C C C
10 9 8 7 6 5 4 3 2 1
CH3 CH3 CH3
2,7,8 - timethyl decane
Lowest sum rule:
2,7,8 = 17
3, 4, 9 = 16
According to lowest locant rule:2,7,8- trimethyl decane is correct name.
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CH3 CH3
1 2 3 4 5
CH3 C CH2 CH CH3 2,2,4 - trimethyl pentane
5 4 3 2 1
CH3
Lowest sum rule:
2,2,4 = 8
2,4,4 = 10
According to both lowest
locant and sum rule
f) Number are separated by comma whereas number and name are separated by dash.
2,2,4- Trimethylpentane
g) First letter of name is always written in capital, there will be no space in in 2 1 suffix and word
root and also between word root and prefix
if two or more than two substituents are present then ‘di’ is used for 2, ‘tri’ for 3, ‘tetra’ for 4.
CH3 CH CH CH3
CH3 CH3
CH32 CH33
CH
CH3 C CH3 CH3 C CH3
2,3 - Dimethyl butane
CH33
CH CH33
CH
2,2 - Dimethyl propane 2,2 - Dimethyl propane
CH3 CH3
CH3 C CH CH3
CH3
2,2,3 - Trimethyl butane
h) If two or more than two different substituents are present then their names are arranged in
alphabetic orders.
C M E
Cl CH3 C2H5
If substituted side chain is present then bis’ tris’ tetrakis is used in place of di, tri, tetra.
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1 2 3 4 5 6 7 8 9
CH3 CH2 CH2 CH2 CH CH2 CH2 CH2 CH3
CH CH3
CH CH3
CH3
CH3
CH3 C CH3
CH3 CH2 CH2 CH2 CH2 CH CH CH2 CH2 CH2 CH2 CH2 CH3
CH CH3
6 - (1,1 - Dimethylethyl - 5 -
CH2 (1 - Methylpropyl)dodeane
CH3
CH3CH2Cl
CH2CH2Cl
4,5 - Bis - (Chloroethyle) octane
Note: in IUPAC system iso and neo are taken in the alphabetic order whereas tert. and sec are not
taken in alphabetic order.
CH3
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1 2 3 4 5 CH3 CH3
CH2 CH CH2 C CH
1 2 3 4 1 2 3
Pent- 1 - en - 4 - yne CH2 C CH2 CH3 CH2 CH C CH3
2 - Methyl but - 1 - ene
C2H5
4 5
3,3 - Dimethylpent -1 - ene
CH3 Cl Br
1 2 3 4 5 CH3
But – 2 -yne
CH3 C C CH CH3 C C CH CH CH3
1 2 3 4 5 6
4 - Methylpent - 2 - yne 5 - Bromo - 4 - Chlorohex - 2 - yne
Q1) Give IUPAC name of the following:
a) CH3 CH CH3 CH3
CH3
h) CH3 CH2 CH2 CH CH2 CH2 CH CH2 CH3
CH3
c) CH3 C C CH CH3 d) CH3 CH CH CH2 CH CH CH3
CH2 C CH2
CH3
f) C2H5 C C C2H5 CH3
C2H5 C2H5 g) CH3 CH C C CH
CH3 CH3
h) CH C CH CH CH3 i) CH C CH2 C CH
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j) CH2 C CH CH2 k) HC C CH2 CH2 CH CH2
CH3
Cl O Cl O 1CHO
1 1 4
3 3 2 2 3
2 CH3 CH CH2 CH3
4 H 4 H
2 - Methylbutanal
Br Br
2 - Bromo - 3 - Chlorobutanal 2 - Bromo - 3 - Chlorobut - 2 - enal
1CHO 1CHO CH3
2 3 4 5 6 2 3 4 5 6
CH3 CH CH CH CH CH3 CH3 CH CH CH CH CH3 CH3 CH CHO
2 - Methylpropanal
CH3 CH3
2,5 - Dimethylhex- 3 - enal 2,5 - Dimethylhex- 3 - enal
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NO2 Cl C2H5
CH3 CH C CH CHO
5 4 3 2 1
Br
3 - Bromo - 3 - Chloro - 2 - ethyl - 4 - nitropentanal
Alcohol: (
Minimum possible no should be given but not chain terminating
3 2 1 1 2 3 OH
CH3 CH2 CH2 OH CH3 CH CH3
Propan - 1 - ol CH3 C CH3
OH
Propan - 2 - ol CH3
2 - Methyl propan - 2 - ol
OH 3 1
2
CH3 CH CH2 CH3 OH
Butan - 2 - ol 3 - Methyl butan - 1 - ol
ketone: (
O O O
Cyanide: (
3 2 1 2 1
CH2 CH CN CH3 CN
prop - 2 - ene nitrile Ethane nitrile
Br CH3 2 3 4
4 CH3 CH CH2 CH3
3 2 1
3 2 1 CH3 CH CN
5 CN 1CN
2 - Methyl propane Nitrile 2 - Methyl butane nitrile
Cl
2 - Bromo - 3 - chloro - 4 - methyl pentane nitrile
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Ester : (R’-COO-R) : Alkyl alkanoate
R’ can be H or can be alkyl group but R always alkyl group
O O
4 – chloro phenylethanoate
3 - chloro phenylethanoate
Cl
O
CH3 C O
2 - Chlorophenylethan - oate
Amine:
Amine:
CH3 CH2 N CH3 CH3 CH2 CH2 CH2 N CH3
CH3 C2H5
N,N - Dimethyl ethan amine
N - Ethyl - N - Methylbutan - 1 - amine
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CH3
CH3 CH2 N
CH3 CH CH2 N CH3
CH3
C2H5 N - Ethyl - N - Methyl Benzene amine
N - Ethyl - 2,N - dimethylpropane - 1 - amine
O O CH3
3 2 1
H C NH2 CH3 C NH2 CH3 C CONH2
Ethan amide
Methaan amide
CH3
2,2 - Dimethyl propan amide
O Cl O
1 CH3
3 2 3C CH2
2
C
1
NH2
4 NH2
C2H5
2,3 - Dimethylbutanamide 3 - Chloro - 3 - Methyl pentan amide
3 amide:
O O
CH3 O CH3 O
C2H5 C2H5
N - ethyl - 3 - methyl -N - propylpentan amide
N – ethyl – 3, N – dimethyl butan amide
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Acid halide: Alkanoyl halide
O O O
CH CH C Cl
CH3 C Cl 2CH3 1C Br
3 3 2 1
Ethanoyl chloride
Ethanoyl bromide CH3
2 - Methyl propanoyl chloride
CH3 O O Br O
Cl Cl Cl
But - 2 - enoylchloride
C2H5 3 - Bromo - 4,5,5 - trimethylhexanoylchloride
2 - Ethyl - 3 - methylbut -2 - enoylchloride
Acid anhydride:
O O
( C O C )
O O O O
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I.U.P.A.C Nomenclature of compounds having 2 or more than 2 similar functional groups:
CH2 OH Ethane - 1,2 - diol CH2 OH
OH
Hexane - 1,2,3 - triol
If 3 or more than 3 similar carbon containing functional group are directly attached to a carbon
chain then functional groups are treated as side chains and numbers are not given to functional
group
COOH CHO CN
CH3 CH3
e) CH3 CH C CH2 OH f) CH3 CH CH CH CH3
CH3 OH
OH h) CH C CH C CH3
g) CH3 C C CH CH3 OH
CH3 CH3
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CH3 CH3
CH3
COOH COOH
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SH OH O
O
O
CH3 C CH2 CH2 OH
OH C OH
4 – hydroxyl butan – 2 - one
Hydroxy methanoic acid
OH CH2 CHO
2 1 O
2 - Hydroxy ethanal
H2N C OH
CH3 CH C C CH COOH
SH OH
5- amino - 2 - hydroxyl - 4 - mercapto - 3 - methylhex - 3 - enoic acid
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Q5) Write the IUPAC name of the following
a) CH3 CH2 CH CH2 CHO b) OHC CH2 CH2 CH2 CN
OH
c) CH3 CH2 C COOH CH3
O d) CH3 C C CH3
OH O
e) CH3 CH2 CH C CH CH COOH f) CH3 CH2 C CH2 CHO
OH O O
g) CHO CH2 C CH2 COOH h) H3C CH CH2 C CH3
O OH O
I) H3C CH CH2 CH CH3 j) HOOC CH CH COOH
NH2 OH OH OH
k) OHC CH2 CH2 C COOH
O
Q6) Write the IUPAC Name.
a) b) CN c)
d) e) Cl H f) Cl CH CH2 OH
Cl
I.U.P.A.C Nomenclature of cyclic compound:
In cyclic compound, cyclo word is used
Cyclopropane Cyclobutane
Cyclohexane
3 3
4 2 4 2
5 1 5 1
cyclohexene
6 6
Cyclohexa-1,4-diene Cyclohexa - 1,3 - diene
If substituents are present then numbering is done according to lowest locant rule
If lowest locant rule is not applicable, then alphabetic order is used for numbering.
CH3 CH3 Cl
3 3 3
2 2 2
1 CH3 1 1
CH3 C2H5 Br
1,1,3 - Trimethlcyclohexane 1 – ethyl – 3 – methyl cyclo 1 – bromo – 3 – chloro
hexane cyclohexane
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If no of C- atom in ring are more or equal than the side chain then ring is taken as present chain
but if no of C- atoms in side chain are more than the ring then the ring is taken as side chain.
CH2 CH3 CH2 CH2 CH3 CH3 CH CH2 CH3
1
3 - Pentylcyclo - 1 - ene
b) ring is saturated, side chain is unsaturated, then side chain is taken as parent chain.
CH2 CH2 CH2
4 6
5
1- (cyclohex -3 – enyl) buto – 1,3 - diene
d) if both are unsaturated and no of unsaturation is same then part with maximum no of C- atom
is parent chain.
e) if unsaturation is same and carbon atoms are also same then cyclic chain is always taken as
parent chain.
4 CH CH CH CH2
3 5 CH CH CH CH2
1 2 3 4 4 1
2 6
1 3 2
5(Buta – 1,3 – dienyl) cyclohexa – 1,3 diene 1 - (Buta - 1,3 - dienyl)
Cyclobuta - 1,3 - diene
Brackets have to be used in complex side chain
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CH3 — CH — CH2 — CH2 — CH3 CH3 — CH — CH2 — CH2 — CH3
2 - Cyclopropyl pentane
CH3
2 - (2 - methylcyclopropyl)pentane
if ring is unsaturated and also contain substituents then numbering is given accn to unsaturation
and if unsaturation and functional group are present then numbering is done accn to functional
group
CH3 OH
3 1
2 4 Cl 2 6
1 3 5
4 - Chloro - 3 - Methylchlorohex - 1-ene 4
Cyclohex - 2- en -1 - ol
if side chain contains functional group then parent chain is side chain.
3 2 1 CH2 CH2 COOH
CH2 CH2 COOH
Cl
3 - cyclo pentyl propanoic acid 3 - ( 3 - chloro cyclopentyl) propanoic acid
If functional group present in cyclic chain is treated as parent chain. If functional group is
present in both then priority order of functional group is used to decide parent chain.
CH2 CH2 CH3 CH2 CH2 CH3
OH OH
parent chain
2 - propylcyclopentan - 1 - ol
if cyclo alkyl group is connected to benzene then benzene is taken as parent chain
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if two or more than two cyclic rings are connected to open chain compounds then open chain is
taken as parent chain.
1 2
CH2 CH2 2 1
CH2 CH2
1,2 - Dicyclo propyl ethane
1 - Cyclobutyl - 2 - Cyclopropyl ethane
if carbon containing functional group are directly connected to cyclic ring then special names are
used for functional group.
CHO CN COOH
O O
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O O OH
NH2
N
O
O O
NH2
CH3 C CH CH3
OH
OH
Cl O Cl O
CH3 — CH — CH2 — C — OH
OH
O O OH
OH
CH3 — C — CH3 CH3 CH CH3
CH 3 O O
CH NH2 — C — NH2
CH 2 CH 2 NH2 NH2
Urea
H H
C
C CH2 CH2 CH2
CH2 CH2
CH2
CH2 CH2 CH
CH2 CH2 2
C C
H
H
H H H
H
C C
H C C
C C
C C H
H H
H
H
CH 3 C C CH 3 CH 3 CH 2 CH CH 2
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1 2 3 1 2 3 4 5
CH2 C C CH2 CH2 CH C CH CH3
CH3 CH3 C 2H 5
1 2 3 4 1 2 3 4 5 6
O O
Condensed formula: In this representation of organic compound, the repeating unit are represented in
brackets and the number of repeating time is represented in subscript. Side chain and substituents are
also represented in brackets.
CH CH3
CH3
Cl CH3
CH3 C CH2 CH3 CH3 C CH3 (CH3)4C
OH CH3
CH3 CH2 3 CH3
CH3 — CH2 — CH2 — CH2 — CH3 CN — CH2 — CH2 — CN (CN)2(CH2)2
CH3
CH3 CH C CH2 CH3 CH3
CH3 OH
CH3 CH3 C
CH3
Q7) Expand each of the following condensed formula into their complete structured formula.
a)
b)
c)
d)
Q8) For each of the following compound, write a condensed formula and also their bond line formula.
a) CH3CHCH2OH b) CH3CH2CH2CH2CH2CHCH2CHO
CH3 Br
OH
c) HOCH2CH2CH2CH(CH3)CH(CH3)CH3 d) N C CH C N
Q9) Write the bond line notation and name of the following and complete structured formula:
a)
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Chapter: ORGANIC CHEMISTRY
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b)
c)
d)
e)
f)
g)
h)
i)
j)
Q10) Expand each of the following bond line formula to show all the atom including carbon atom and
hydrogen.
a) b) c) d)
OH
Q11) Write bond line formula for Isopropyl alcohol, 2,3 di methyl butanal , Heptan- 4- one
Q12) Give condensed and bond line structured formula and identify the functional group present if any,
a) 2,2,4 – trimethylpentane
b) 2 –hydroxy – 1,2,3 – propane tricarboxylic acid
c) Hexane1,6 dial.
Nucleus
If the functional group is directly attached with benzene ring they are named as derivative of benzene
according to IUPAC Name.
CHO COOH
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Cl NO2 OCH3 CH3
Always apply priority order of functional group and lowest locant rule
COOH OH OH
1
2
OH Cl
3-Hydroxybenzenecarboxylic Phenol 3-Chlorophenol
acid
OH OH Cl
Cl NO2 NO2 Cl
(o-Dichlorobenzene)
Br
NO2 1,2-dichlorobenzene)
2,4,6-Trinitrophenol (picric acid)
4-Bromo-2-Chlorophenol
Cl NH2 OCH3
Br
Methylbenzene 1-Bromo-3-Chlorobenzene
(Toluene)
Important common name:
O
OH CH3 NH2 COOH CHO OCH3 C CH3
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Q13) Write the structured formula of
a) –
b)
c)
d) – – – –
ISOMERISM: those compounds which have some molecular formula but different physical and
chemical properties are known as isomers. This is phenomena is known as isomerism
Example: Butane
C4H10
CH3
(n-butane) isobutane
Butane 2-methylpropane
Higher boiling pt. lower boiling pt.
Butane and isobutene are isomers of each other
ISOMERISM
CH3
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CH3 CH3
H3C CH2 CH2 CH2 CH3 CH3 CH CH2 CH3 CH3 C CH3
CH3
n-pantane isopantane neopantane
pantane 2-methylbutane 2,2-dimethylpropane
CH3
1) CH3 CH2 CH2 CH2 CH2 CH3 4) CH3 C CH2 CH3
(6C)
CH3
CH3
(4C)
2) CH3 CH CH2 CH2 CH3
CH3 CH3
(5C)
5) CH3 CH CH CH3
CH3
(4C)
3) CH3 CH2 CH CH2 CH3
(5C)
1 and 2 chain 1 and 3 chain 1 and 4 chain 1 and 5 chain
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Chain isomerism in alkene: in writing the chain isomers for the alkenes, the position of the double
bond is may be same or different but length of chain should must be different. For example, chain
isomers of molecular formula and are shown below:
Butene Pantene
Chain isomerism in alkynes: In alkynes, chain isomerism is shown by the compounds with five or
more carbon atoms. For example, the molecular formula represents the following two chain
isomers.
Pantyne CH3
(5C) (4C)
b) Position isomerism: position isomers have same molecular formula but different structural formula due
to different position of substituent, functional group or multiple bonds (double and triple bonds).
C3H7Cl C3H7OH
Cl OH
CH2 CH CH2 CH3 CH C CH2 CH3
C4H8 C4H6
CH3 CH CH CH3 CH3 C C CH3
Butene Butyne
CH3 CH3 CH3
CH3
CH3
CH3
O-xylene M-xylene P-xylene
1,2-dimethylbenzene 1,3-dimethylbenzene 1,4-dimethylbenzene
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OH OH OH
OH
OH
OH
Catechol Resorcinol quinol
1,2-dihydroxybenzene 1,2-dihydroxybenzene 1,2-dihydroxybenzene
Note: in alkane, position and chain isomerism cannot exist together. If two isomers are chain
isomers then they cannot be positional isomers and vice versa. Because if the position of alkyl group is
changed then parent chain maybe changed.
Chain isomer of Butane:
CH3
H3C CH2 CH2 CH2 CH3 CH3 CH CH2 CH3 CH3 C CH3
CH3
n-pantane isopantane neopantane
pantane 2-methylbutane 2,2-dimethylpropane
Chain isomer of Hexane:
CH3
1) CH3 CH2 CH2 CH2 CH2 CH3 4) CH3 C CH2 CH3
(6C)
CH3
CH3
(4C)
2) CH3 CH CH2 CH2 CH3
CH3 CH3
(5C)
5) CH3 CH CH CH3
CH3
(4C)
3) CH3 CH2 CH CH2 CH3
(5C)
1 and 2 chain 1 and 3 chain 1 and 4 chain 1 and 5 chain
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CH3 CH3 CH3
3) CH2 C CH2 CH3 4) CH2 CH CH CH3 5) CH3 C CH CH3
(4C) (4C) (4C)
1 and 2 position 2 and 4 chain, position
1 and 3 chain 2 and 5 chain
1 and 4 chain 3 and 4 position
1 and 5 chain, position(position of = bond change) 3 and 5 position
2 and 3 chain, position 4 and 5 position
Functional group isomerism: - Organic compound which have same molecular formula but different
functional group is known as functional isomer. This phenomenon is called functional isomerism.
Aldehyde and ketone [Formula; ] Alcohol and ether [Formula ( )]
O O CH3 CH2 OH H3C O CH3
propanone Propanal
minimum 2 carbon need as ether is with minimum
2 carbon
minimum 3 carbon need as ketone is with
minimum 3 carbon
Carboxylic acid and ester Cyanide and isocyanides
O
c) Metamersim: - compounds have same molecular formula but different structures due to different nature
of alkyl groups on both side of same functional group.
Since Metamers have same functional group so metamers cannot be functional isomers. i.e metamers
and functional isomers cannot exist together
Note: alkene and alkyne do not show Metamersim according to new definition.
compound should be hetero nuclear i.e at least one different atom other than C should be also present
like N or O
ether, thio ether, ketone, ester, acid anhydride,
O S O O O O
C C O C O C
NH N O O
C NH C N
Example of metamers:
Example of metamers:
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1) ether, thio ether, 20 Amine
H
R O R' R S R' R N R'
ans: 3
Actually 3 is right answer because according to formula ( ) it have 3 metamers as we see
above. But according to structure there are 2 metamers of each other.
CH3 O CH CH CH3
nature of alkyl
group changed
CH3 O CH2 CH CH2 so metamers
ans: 6
1) H3C O CH2 CH2 CH2 CH3 5) CH3 CH2 O CH2 CH2 CH3
CH3 CH3
CH3 CH3
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O
CH3 C CH2 CH2 CH3
O
total 3 metamer of formula C4H10O
CH3 C CH CH3
u.f =1
CH3
1&2 no metamers
O 1&3 metamers
2&3 metamers
CH3 CH2 C CH2 CH3
2) Type of intermediate:
In any chemical which is completed in more than one step, intermediate is prepared but when is
completed in one step only transition state is prepared, not intermediate.
No. of transition state = no. of steps:
No. of intermediates = no. of steps - 1
T.S T.S1
R P Heat T.S2
Heat T.S3
R I.M1
P I.M2
P
Path R
single step reaction
path
3 step mechanism
Reaction intermediated:
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(1) Carbocation: C – atom having 6 valence (all six are bonded) & having positive charge on it.
+
SP2 , trigonal planar, diamegnetic
C
Three bonds lie in the same plane and empty orbital lie to perpendicular plane
Q1) The total no electrons in is Q2) The no. of paired electrons in is
i) 6 (i) 6
ii) 8 (ii) 8
iii) 4 (iii) 4
iv) 3 (iv) 3
Q3) The total no of valance electrons in is Q4) The total no of paired valance electrons in is
(i) 6 I) 6
(ii) 8 II ) 8
(iii)4 III ) 4
(iv) 3 IV ) 3
Exception – Acylium cation is not carbocation because it is sp hybridised
CH3 C+ O CH3 C O+
Acylium cation
(not carbocation) more stable as octate of all completed
(2) Carbanion: C – atom having 8 valence (3) Carbon free radical:
electrons (6 bonded, 2 unbounded) & negative C – atom having 7 valence electrons (6 bonded &
charge on it 1 unbonded & zero charge on it)
Carbon free redical:
C this electron is in
H H C · unhybridized p orbital
H
sp3, pyramidal, diamegnetic (7e–)
SP2 , planar, paramegnetic
Q5) The unbonded of methyl radical is present in
i) s
ii) p
iii)
iv) sp
3) Types of regent:
Reagent is the organic/ inorganic substance which reacts to form product.
Reactant + reagent Product
Main Product
Reactant
Reagent side product
1st reagent: Electrophile (E+): Electron loving species or L.P acceptor i.e (Lewis acid)
a) all positively charged species having incomplete octate or expandable octate
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Eg. H+, Cl+, Br+, I+, CH3, NO2, H3C CH2 H3C C CH3
CH3
PCl4 complete octate but having extandable octate due to presence of vacant d orbital
b) neutral electrophile:
having incomplete octate (vacant p orbital)
group 2 group 13 d block compound due to vacant 4p and 4 d orbital
BeH2 BF3,BCl3, BBr3, BI3,B2H6, BH3,
ZnCl2, FeCl3 ,FeCl2
AlCl3,
Having vacant d orbital
group 14 group 15 group 16 group 17
OH-
if central atom is joined with high E.N element by multiple bond then substance behave as L.A
For Ex: CO2, NO2
C
CH3 H methyl free radical is not a electrophile as it cannot accept
H a lone pair of electron.
H
Q18) Using curved arrow notation show the formation of reactive intermediate when following
covalent bond undergoes heterolytic fission.
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a)
b)
c)
Q19) For the following bond Cleavage, use curved arrow to show the electron flow and classify each as
hemolysis or heterolysis, identify reactive intermediate produced as free radical, carbocation and
Carbanion.
(a) CH3O OCH3 CH3O + OCH3 (b) O + OH O + H2O
E
(c) (d)
Br + Br + E
Electronic effect (or electron displacement effect): For chemical reactions, there should be
attraction b/w molecules and for attraction, opposite charges are required.
Charges are created due to displacement of and are displaced due to some internal or external
effect.
Internal / Permanent effect: Permanent effect means charges are permanently present either there
is any reaction or not.
These are present in form of polarities means partial charge and this is permanent.
CH3 F
Charges are produced in permanent effect is due to
Inductive effect
Resonance or mesomeric effect.
Some other permanent effects are also possible but these are not directly related to polarity
Hyper-conjugation
External / temporary: Charges are created in neutral molecule in presence of reagent. These are
complete charges these are temporary.
H+
H2C CH2 H3C CH2+
Electromeric effect
1st Electronic displacement:
Inductive effect: in organic compound, covalent bond is formed by the mutual sharing of electron b/w
two similar atoms or dissimilar atoms. After the bond formation, shared pair of bonded electron are
partially shifted towards more electronegative atom.
Inductive effect:-The process of displacement of electrons along the chain of carbon atoms due to the
presence of an electron donating or electron withdrawing group at one end of the chain is called
inductive effect.
Note: Only sigma bond is shifted in inductive effect
CH3 > CH2 > CH2 > CH2 > Cl
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a) b) –
effect:- If the substitute attached to the end of the carbon chain is electron donating which loose
toward a carbon atom, the effect is called + I effect. (no effect after 3rd cabon)
C < C < C < CH3 (+I-effect)
– effect: - If the substitute attached to the end of the carbon chain is electron withdrawing which
withdraw the e- away from a carbon atom the effect is called –I effect.
< < <
C C C X (-I-effect)
–
Acid character of carboxylic acid: acids are those compounds which give H+ ions when dissolved in
water
RCOOH RCOO- + H+
more more
acidic stable
Arrange the following in decreasing order of acidity:
CH3 CH3
Cl Cl F NO2
CH3 — COOH Cl CH2 COOH Cl CH COOH Cl C COOH F C COOH NO2 C COOH
Cl F NO2
(A) (B) (C) (D) (E) (F)
CH3 CH2 CH2 COOH CH2 CH2 CH2 COOH H3C CH CH2 COOH CH3 CH2 CH COOH
Cl Cl Cl
(a) (b) (c) (d)
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CF3 COOH CCl3 COOH CBr3 COOH CI3 COOH
(a) (b) (c) (d)
F Cl Cl F Cl F
CH3 CH CH COOH CH3 CH CH COOH CH3 C CH2 COOH CH3 CH2 C COOH
b F c Cl
a d
COOH
COOH
O COOH O O
CH3 C OH CH3 C O
F CH2 CH2 OH F CH2 CH2 O
CH3 CH3
CH3 CH2 CH2 OH CH3 CH2 CH2 O
CH3 CH3
CH3 CH OH CH3 CH O
Stability order of acid will be same as stability
order of anion. CH3 CH2 OH CH3 CH2 O
Rule 1: more will be charge on reaction
intermediate (cation or anion), more will be CH3 OH CH3 O
reactivity & less will be it’s stability.
Stability of carbocation:
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a) if (+) I group is present in carbocation then they decreases + ve charge by donating the electron density
toward +vely charged carbon and hence increases the stability of carbocation.
b) If (– I) group is present in carbocation then they increase the +ve charge by withdrawing the electron
density and hence decreases the stability of carbocation.
+ I group ses the stability of carbocation
- I group ses the stability of carbocation
Stability of carbocation
H H CH3 CH3
<
<
H—C CH3 —
> C CH3 —
> C CH3 —
> C
<
H 1 +I H 2 +I H CH
(ii) (iii) 3 +I (iv)3
(i)
I < II < III < IV Stability order
Cl
<
CH3 CH2
<
<
CH3 —
> C > Cl —
< CH2 —
<C
<
<
CH3 CH2
3(+I) chage
<
Cl
3(–I) chage
Stability of Carbonions. Carbonions are the species having – ve charge on carbon.
If (+) I group is present is present in carbanion, then it ses the – ve charge so the stability of
carbanion.
If (–) I group is present in carbanion then ses the –ve charge so the stability of carbanion.
+I group ses the stability of carbanion
-I group ses the stability of carbanion
<
H — C: CH3 —
> C: — C:
CH3 > CH3 —
> C:
<
H 1+I H 2 +I H 3 +I CH3
(a) (b) (c) (d)
a>b>c>d
Cl
<
CH3 CH2
>
CH3 —
> C: < Cl —
< CH2 — C:
>
CH2
CH3
<
Cl
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1> 2
H
H+ H reso
hyper CH2 CH CH2+ CH2 CH CH2
H C C H C C
H sp2 sp2
H
H H
in the same plane
carbon
sp2
sp3
CH3
no overlapping so inductive is least effective
Note:
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H + H H
H
+
H — C — CH2 +
H—C CH2 H C CH2 H — C CH2
+
H H H
H
Note: No of hyper conjugation structure stability
Q: why hyperconjugation is also known as no bond resonance?
H
H H+ H
hyper
H C C H C C
H H
H H
-H+ no condition for resonance
H
H C C
H H
now resonance possible as condition for resonance is fullfilled since this is occure when H dissociate it's bond
and create the possibility of resonance that's why it is called no bond resonance
stability of carbocation
CH3
H3C C CH3 CH CH3 CH3 CH2 CH3
CH3
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Q: arrange the following in decreasing order of + I effect or electron donating tendency towards
benzene ring?
CH3 CH3
4>3>2>1
5 2 6 4 9 8
1 7 3 4 4
2>4>5>3>1 hyper same then see inductive
b) Hyper conjugation in alkenes;
Note: like alkene, hyper-conjugation also take place in alkyne.
H
H
3H CH2 CH CH2
so more H more will be resonance that's why we are saying that more H in alkene,
more it is stable
Hyperconjugation is also called no bond resonance as resonance arise when Hydrogen dissociate it’s
bond
CH2 CH2 CH3 CH CH2 CH3 CH CH CH3 CH3 C CH CH3 CH3 C C CH3
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H H H+
H
c
H C H +
H C H H C H H C H+
sp2
sp2
: : :
Resonance
H H
+ +
H C H H C H
Ans: According to inductive effect 1st is more stable but according to hyper-conjugation 2nd is more
stable as it has more and hyper-conjugation dominates.
Q21) Explain the term inductive effect and Electromeric effect .which electron displacement effect
explain the following correct order of acidity of carboxylic acid.
a)
b)
Ans:
a) The order of acidity is explained by of the chlorine atoms. Greater the magnitude of –
effect, easier will be the release of ion and stronger will be acid.
b) The order of acidity is explained by of the alkyl group atoms. Less the magnitude of
effect, easier will be the release of ion and stronger will be acid.
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Q27) Arrange the following in increasing order of acidic strength:
Q28) What is hype conjugation? Which is the most stable among the following?
(a) CH3CH2, (b) CH3, (c) (CH3)3C, (d) (CH3)2CH
Q29) What is Carbanion? How is it formed? Which is the most stable among the following?
Negative Electromeric effect (- E effect):- In this effect, electron of the multiple bond are transferred
to that atom to which the attacking reagent does not get attached.
O O
C + CN C
CN
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not leave its molecular orbital. There is only leaves its orbital and taken up a new position.
a distortion in the shape of orbitals involved
in the overlap.
3. The presence of the outside attacking reagent 3.The presence of the outside attacking reagent
is not needed. is quite essential.
4. There is a partial separation of changes. 4.There is a complete separation of charges.
5. No ions are formed. 5.Ions are formed.
6. The presence of multiple bond is not 6.The presence of multiple bond is essential.
essential.
Resonance/ mesomeric effect:
Resonance: Resonance is defined as existence of more than one structure for same compounds due to
delocalization of .
All such structures are completely hypothetical and are called canonical or resonating structures.
Real structure is hybrid of all possible resonating structures. It is most stable structures of its
compound.
More will be stability of resonating structure, more will be its contribution in hybrid structure
The no of most contributing resonating species in any charged species = no . of bonds in
conjugation +1
O O O O
Resonating or mesomeric effect: Charges are created due to delocalization of electrons b/w
functional group and benzene ring or conjugated carbon chain. These charges are always present only at
alternate C- atoms and this effect is distance independent. Resonating effect remains same up to infinite
no of carbon but inductive effect became negligible after 4 carbons.
+ R / + M effect: It is delocalization of electrons away from the functional group and toward
benzene ring or conjugated system. Due to this effect – ve charges are created at alternate C atom.
..
..
CH2 CH — CH CH — NH2 CH2 CH— CH — CH NH2 CH2 — CH CH — CH NH2
– – +
(4) CH2 CH CH CH NH2
Rules for stability of non- equivalent resonating structures:
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Rule 1: resonating structures without charge is most stable
Rule 2: If resonating structures is having charge then structures with more numbering of covalent bonds
will be more stable [ as it have more no of atom with complete octate]
Rule 3 if number of covalent bonds are same in charged structures then the structures in which –ve
charge is present on more electronegative atom and +ve charge present on less electronegative atom will
be more stable.
Rule 4 If above 3 rules are same, then the structures in which opposite charge is present at minimum
distance will be more stable
CH2 CH CH CH NH2
Necessary condition for + R / + M effect: functional group attached with benzene ring or conjugated
system should have
at least one lone pair
negative charge
Or can show hyper conjugation
Note: functional group should be single bonded.
NR2 O O H O CH3 O
OH
NH C CH3 O C CH3
Cl Cl Cl Cl
Chlorobenzene
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OH OH OH OH
phenol
– R / M effect : It is delocalization towards functional group away form C chain or benzene ring
it creates + ve changes at alternate C atoms.
H H O H O H
O O
C C C C
O O O
O
CH2 CH CH CH CH
Necessary condition for - R / - M effect: When a group withdraw electron from conjugated system
having
= or
+ve charge (vacant p- orbital on just attached element of functional group )
No lone pair on directly attached atom.
O O O O O
O O — C N ,
O
— C — OH —N O — C — OCH3
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O O O O O O
O O
N N N N
CH3 CH CH CH O CH3 CH CH CH O
O O
H3C C H3C C
O O
I II III
O O O
Q34) Explain why alkyl groups act as electron donors when attached to a π system.
Ans: Due to Hyperconjugation, alkyl group acts as electron donors when attached to π system
Q35) Show how the following Carbanion is stabilized by resonance?
O
H2C C CH3
Q37) What are hybridization states of each carbon atom in the following compound?
a)
b)
c)
d)
e)
Q38) In the organic compound the pair of hybrid orbital involved in
the formation of bond
a)
b)
c)
d)
Q39) Indicate the bond in the following molecule and also count the total no of the bond.
a)
b)
c)
d)
e)
Homologous series:-Defined as group of structurally similar compound all the member of which
contain the same functional group and any two adjacent member of which differ by group.
Ex
Q40) Draw formula for the first five member of each homologous series beginning with the following
compound
a) b) c)
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Detection of Carbon and Hydrogen: We have stated that carbon and hydrogen are the essential
constituents of all organic compounds. They can be detected in the laboratory as follows:
Principle: The pure and dry organic compound is heated strongly with dry cupric oxide in a hard glass
tube. As a result, carbon gets oxidized to carbon dioxide while hydrogen present is oxidized to water.
→
The presence of can be detected by passing the gas through lime water which becomes milky. The
water vapours are brought in contact with anhydrous (white) which gets hydrated to
(blue).
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Procedure: In order to detect carbon and hydrogen, a small amount of the pure and dry organic
compound is mixed with about double the amount of pure and dry cupric oxide in a hard glass tube.
The tube is fitted with a delivery tube having a bulb in the center. The other end of the delivery tube is
dipped in a tube containing lime water as shown in the Fig. The bulb in the delivery tube is packed with
anhydrous copper sulphate. Upon heating strongly, the organic compound undergoes oxidation to form
vapour and . Whereas the changes the colour of copper sulphate to blue, the turns
lime water milky.
In case, the compound contains sulphur in addition to carbon and hydrogen, then sulphur will be
oxidized to sulphur dioxide by cupric oxide. The gas will also turn lime water milky due to the
formation of calcium sulphite.
→
Sulpher present in organic compound combine with sodium to form sodium sulphide
Halogen present in organic compound combine with sodium to form sodium halide
Cyanide, sulphide and halide so formed in sodium fusion are extracted from fused mass by boiling it
with distilled water. This is called sodium fusion extracted or Lassaigne’s extracted and this extracted is
used for test of nitrogen, sulpher and halogen.
b) Test for Nitrogen:-The sodium fusion extracted is heated with ferrous sulphate solution and a few drop
of ferric chloride solution is then added then acidified with dilute concentrated sulphuric acid. The
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formation of Prussian blue colour confirm the presence of nitrogen. The Prussian blue colour is due
to formation of Ferric ferrocyanide
2nd method: Sodium nitroprusside test: - In sodium fusion extract ( , a few drop of sodium
nitroprusside are added. The appearance of violet coloration indicated the presence of sulpher.
i. If a white ppt formed which is soluble in Ammonium hydroxide, then it show the presence of chlorine
in organic compound
ii. If a dull yellow ppt formed which is slightly soluble in Ammonium hydroxide show the presence of
Bromine in organic compound.
iii. If a bright yellow ppt formed which is completely insoluble in Ammonium hydroxide show the
presence of iodine in organic compound.
Q42) Why is nitric acid added to sodium extract before adding silver nitrate for testing halogens?
Ans: Function of nitric acid:-If Nitrogen or Sulpher is also present along with halogen in the organic
compound then it will interface with silver nitrate test for halogen.
Therefore the sodium fusion extract containing sodium sulphide and sodium cyanide along with sodium
halide is first boiled with concentrated Nitric acid. Nitric acid decompose sodium cyanide or sodium
sulphide formed during Lassaigne’s test to form vapour of . Which escape from solution.
Q43) Why is an organic compound fused with sodium for testing nitrogen, halogens and sulphur?
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Ans: On fusing with sodium, these elements present in the compound are converted into their sodium
salts and which are water soluble. From the solutions, these elements can be
detected by suitable tests.
Q44) It is not advisable to use sulphuric acid in place of acetic acid for acidification while testing
sulphur by lead acetate test. Assign reason.
Ans: Lead acetate will react with sulphuric acid to give white precipitate of lead sulphate. This will
interfere with the detection of the test for sulphur.
Q45) On complete combustion 0.246 g of an organic compound gave 0.198 g of carbon dioxide and 0.1014 g
of water, determine the % age composition of carbon and hydrogen.
Q46) of an organic compound forms of and of water on combustion.
Calculate the percentage of carbon and hydrogen in the compound.
Ans:
Q47) of an organic compound gave on combustion of and of . Calculate
the percentage of carbon and hydrogen in the compound.
Ans:
Q48) An organic compound gave the following results on analysis of the compound gave
of and of . Calculate the percentage of carbon and hydrogen in the
compound.
Ans:
For estimation of Nitrogen:- There are two method for estimation of nitrogen
a) Dumas method b) Kjeldahl’s method.
a) By Dumas method
Step I. Calculate of the volume of nitrogen at
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Chapter: ORGANIC CHEMISTRY
Avogadro Chem Point
This can be calculated with the help of gas equation as follows:
Experimental conditions Conditions
b) Kjeldahl’s method: An organic compound containing nitrogen heated strongly with conc. .
Due to heating the nitrogen present in organic compound is converted into ammonium sulphate. The
ammonium sulphate is then heated with excess of sodium hydroxide. The ammonia gas thus liberated is
absorbed in a known excess of a standard solution of acid whose molarity is known.
→
The volume of the acid left unused is determined by titrating it against a standard alkali solution
such as
Note:
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Chapter: ORGANIC CHEMISTRY
Avogadro Chem Point
( )
Q51) 0.35g of an organic substance was KJeldahlised and the ammonia obtained was passed into 100
ml of of . The excess acid require 154 ml of for neutralization. Calculate the %
age of Nitrogen in the compound.
Ans:
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Chapter: ORGANIC CHEMISTRY
Avogadro Chem Point
Q52) of an organic substance was heated with conc. and then distilled with excess of strong
alkali. The Ammonia gas evolved was absorbed in of which required
for neutralization at the end of process. Determine the %age of nitrogen in the Compound.
Ans: 14.54
Q53) A sample of of an organic compound was heated according to Kjeldash’s method. The Ammonia
evolved by absorbed in of . The Residual acid required of solution of
NaOH for neutralization. Find the % age of nitrogen in the compound.
Ans: 56%
Q54) During estimation of nitrogen present in an organic compound by Kjeldahl’s method, the Ammonia
evolved from of the compound in Kjeldash’s estimation of nitrogen, neutralized of
. Find out the % age of nitrogen in the Compound.
Ans: 28%
Q55) In caries method of estimation of halogen of an organic compound give . Find out
the % age composition of bromide in the compound. (Atomic mass of Ag = 108, Atomic mass of
Ans:
[ ]
Q56) 0.3780 gm. of an organic chloro compound, gave 0.5740g of silver chloride in caries estimation.
Calculate the % age of chlorine present in the compound. . (Atomic mass of Ag = 108, Atomic mass of
Ans:
Q57) In sulphur estimation, 0.157g of an organic compound gave 0.4813g of barium sulphate. Calculate the
% of sulpher in the compound?
Ans:
Q58) An organic compound contain 69% Carbon and 4.8% Hydrogen. The remainder being oxygen.
Calculate the mass of CO2 and water produced when 0.20 of this substance is subjected to complete
combustion.
Ans:
Q59) In the Lassaigne’s teat for nitrogen in an organic compound. The Prussian blue colour is obtained due
to the formation of:
(a) (b) (c) (d)
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Chapter: ORGANIC CHEMISTRY
Avogadro Chem Point
Q60) Which of the following carbocation is most stable?
(a) (CH3)3C. CH2 (b) (CH3)3 C (c) CH3CH2 CH2 (d) CH3 CH CH2CH3
(b)
(a) (c)
OMe
OH O OCH2CH2N(C2H5)2 CH CHNO2
Q62) Carbon tetrachloride does not give a white precipitate upon heating with silver nitrate solution. Is
it correct?
Ans: Yes it is correct. Carbon tetrachloride is a completely non polar covalent compound
whereas silver nitrate is ionic in nature. Therefore, they are not expected to react and a white precipitate
of silver chloride will not be formed.
Q63) Ethyne is a stronger acid than propyne. Explain.
Q64) What are and effects? Illustrate with one example of each.
Q65) Electromeric effect is only a temporary effect. Comment.
Q66) What is the state of hybridization of carbocation?
Q67) What is the effect of introducing an alky group on the stability of carbocation?
Q68) What is inductive effect? How does inductive effect help in explaining relative strengths of organic
acids?
Q69) What is the effect of introducing an alky group on the stability of a free radical?
Q70) Discuss the various conditions essential for resonance.
Q71) Define chain isomerism with example?
Q72) Define position isomerism with example?
Q73) Define functional isomerism with example?
Q74) Define Metamerism with example?
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Chapter: ORGANIC CHEMISTRY