☒¥

Basic

÷
Organic

Chemistry

KEEP
CALM
Organic compounds:- The compounds c were obtained from living
organisms.

Vital Force theory (VFT) :- No organic compound can be prepared in a

[Berzelius] lab as it requires a mysterious force called
vital force c exists only in living organisms.

Urea was first artificially prepared organic compound in lab by

#

Wohler.
i
Characteristics of c-atom:-
Tetravalency:- Valency = 4
Electronic configuration:- 2,4
At. no :- 6
 Tendency to form multiple bonds
on

Double bond Triple bond

Eg:- CH2 — CH2

HCHO — O CH3 — C — N

Catenation:- Self linking property of an atom.

-

Representation of organic compounds:-

1) Complete structural formula:- All covalent bonds are shown
in this method. H O
H H
H — C —H H—C—O—H H—C—C—O—H

H H H
2.) Condensed structure :- Atleast one covalent bond is hidden.

Eg:- CH3—CH3 CH3—CH—CH2 CH3—COOH

3.) Bond-line formula :- Straight lines are used to represent a

Intersection pts Molecule/compound
i.
3.3
•

W
r
÷
•

—> C atoms & attached H-atoms are not written.

E-
qÉ
E
 Determine total no. of sigma and pie bonds:-

To
9
EEE

⇐
-0

É
is
¥É
④

Hybridisation and shape:-

No of Bond Hyb Pair orbitals Shape Bond angle

6

Tetrahedral 109

0
4 SP3 0
1 Trigonal planar 120

0
3 SP2
SP 2 Linear 180

0
2
 Eg:- Alkene will be a planar molecule.

E-
a-

•
In cumulated polyene/Allene

%
T
No. of double bond and ring in Allene

÷
1-
⇐

-
.
-

-
-

-
If ODD
-

If EVEN

Ei
U
-

A B A OR B

Parallel

A B
 Applications of hybridisation:-
Electronegativity
C>C>C SP3 [25%]
SP SP2
[50%] [33.3%]
Bond length
B.L. SP3 > SP2 > SP

Degree of unsaturation / Index of hydrogen Deficiency:-

—> No. of moles of H2 molecules c are required to remove bonds &
rings from it. D.U = sum of rings + pie bonds
 ÷
E
CH3—CH2—CH3

E
E
÷÷÷¥
É or n m
o v E
11 N
nH2

nH2

E
É
É En
E.g :- CH3—CH = CH2

n
É
o
n
,
É z
N
-0
E É
É E u
Classification of organic compounds:-
Based on structure
Open chain/Acyclic/Aliphatic Closed / Cyclic chain
Saturated Unsaturated Homocyclic/ Heterocyclic
C—C C C/ C C Carbocyclic
(Single bond) Pyranose/
Eg Benzene
Furanose ring
Alicyclic Aromatic Alicyclic Aromatic
Have properties similar (Satisfy hackal’s

:
to aliphatic compounds rule)
 Based on functional groups
—COOH Carboxylic acid
—SO3H Sulphonic acid
C2O3 Acid anhydride

H/R—C—O—R Ester

R—C—R Ketone

R—SH Thioalcohol

R—O—R Ether
R/H—C—X Acid halide

R/H—C—N Acid Amide/ Amide

R—CN Cyanide

R—NC Isocyanide

Aldehyde
R/H—C—H

R—OH Alcohol
R/H
R—N Amine
R/H
R—S—R Thioether
 Homologous series:-
A series/group of compounds having same functional group but
different molecular formula.

Have same general formula

rarer

Have same chemical properties

Successive members of a homologous series differ by CH2 unit.
No homologous series can have more than one different general
formula.

Types of C-atoms
CH3 CH2 C—H C
1 : 4
:
2 3
Types of Alkyl halides & Alcohol:-
C—OH C—Cl

1 —> 1

ii.
1 —> 1
: : :
2 —> 2 2 —> 2
3 —> 3

o
3 —> 3

at

%
0m

Types of Amines:-

NH2 NH N N

1
.

0
4
o

3
☒:¥

IUPAC
¥
NOMENCLATURE

TAKE IT EASY
Word root:- Represent total no. of C-atoms in longest / principal /
main C - chain.

n Word root n Word root

1 Meth 6 Hex
2 Eth 7 Hept
3 Prop 8 Oct
4 But 9 Non
5 Pent 10 Dec
1 Suffix / Primary Suffix:-

Represents Saturation / Unsaturation present in C-chain .

— ane , —> ene , —> yne

1 Prefix / Primary prefix:-

Represents nature of parent C-chain.

Open chain Cyclo

2 Prefix / Secondary Prefix :-
Represents side chains / substituents attached with main C-chain.

X Halo NO2 Nitro

F Fluro NO Nitroso
Cl Chloro OR Alkoxy
Br Bromo OCH3 Methoxy
I Iodo 0C2H5 Ethoxy
R Alkyl
CH3 Methyl C—C Epoxy
O
1
2 Suffix / Secondary Suffix:-
Represents principal functional group present.

Functional group 2 Suffix 2 Prefix

:
COOH Oic acid Carboxy
Carboxylic acid
SO3H Sulphonic acid Sulpho

O O
C—O—C Oic Anhydride
Functional group 2 Suffix 2 Prefix

:
O Oyo halide Halo carbonyl
C—X Carbonyl halide
O
C — NC Amide Carbamoyl
Carboxamide
CN
Nitrile Cyano
Carbonitrile

NC Isonitrile Isocyano

al Oxo
CHO
Carbaldehyde Formyl
Functional group 2 Suffix 2 Prefix

0
0
O
one Keto
C Oxo
OH ol Hydroxy
SH thiol mercepto

N amine amino
O oate alkonyl oxy
C O carboxylate alkoxy carbonal
:

2 P + 1 P + W.R + 1 S + 2 S
:
 How to select Principal C - chain?
Multiple bonds
rrr No. of C-atoms
No. of substituents

Numbering:- P.C.C > Multiple bond > lowest set of locents >
Alphabetical order
(1)

4-Ethyl,3 methylheptane

(2)

3-Ethyl,2 methylhexane
(3)

4-Ethyl 5 methyloctane

(4)

3,4 dimethylheptane
(5)

8
2 Chloro 4 methylpentane

(6)

6-Bromo 3 methylhex-2ene
(7)

or
2-Bromo 5 Chloro 3-Ethylhex-3-ene

(8)

5-Bromo 4 methylhex-2-yne
at
(9)

3[1-Bromo ethyl]2,4 dimethyl

hexa 1,4 diene
oh

(10)

3-Chloro 4 ethyl
5-methyl
3

hex-4en-1-yne
(11)

3-ethyl pent-3en
-2one

(12)

4 Ethyl 3,5 dimethyloctane

 8
(13)
%
2,2 Dibromo 4-Chloro pentane
&

(14)

3 Ethyl 4 nitro hex-2-ene

(15)

4-Ethyl 5 methyl oct-ane

(16)
oh

3[2-Bromoethyl] penta 1-3

diene
(17)

2-Ethyl 3 methyl hex-1-en-4yne

(18)
Z

4-Ethyl hept-2ene-6yne
 E
(19)

3[1-Bromomethyl]
pent-4ene-2-ol

Complex substituent :- Substituted substient is called complex

substituent.
Always written in Brackets
r
(1)

3ethyl 4methoxy
Pent-4-en-2 amine
:
(2)
El

3-Chloro 2 ethenyl
Pent-4-en-1amine
 gg
Firstly always write
(3) substituent attaches
to ester.

Methyl 4,5 Bis[1-bromoethyl]

hex-5-enoate
°

(4) £

4[1,1 dimethylethyl]
2-ethyl hex-5-enoic acid
(5)

£
3-ethyl 4 methyl pent-4-en
2-isonitrile
:>
(6)

3-Bromo-N methyl N-methyl

But-3-en-amide
 É
(7)

4 Amino-3-ethyl-5methyl
hept-5-en-2-ol
O

(8)
E

3-Bromo 2 methyl but-3ene-

oic acid
(9)

§
0
I

2-ethyldiene 3 nitrohex-5-en-1ol
3

(10)

2-Ethyl 3[1-methylpropyl]
pent-4-en-1-nitrile
(11)

€
3-ethyl-N-methyl pent-4
en-2-amine

(12)

3-ethyl 4hydroxy 5 methyl

:

hex-5-ene-2one
(13)

÷ 4-keto 2,5 dimethyl

heptanal

(14)
I

If carbon aldehyde part of PCC, then 3-ethoxy-2-methyl 5-oxo

oxo. pentanoic acid
 •
(15) 0

: Ethyl 2-ethoxy -4hydroxy

5-methyl-6-oxo-hexonate
I

(16)
0

If terminal grp consider as

3

substituent,then except C- of
aldehyde no other C is count.

5 Cyano-4ethoxy
2methylpent-3-en-1 oic acid
 O

E
(17)

C of ester not attached with

I
E

PCC Alkanoyloxy

°
O
4-Ethanoyloxy 3-nitrobut-2en-oic acid

(18)
O

3ethyl hex-2-4diol
(19)
I
E
3-Amino 2 ethyl pentane,
1,5 dioic acid
É
(20)
.

E
E-

Butane 1,2,4 tricarboxylic

☐
①

acid
 0
(21)

0
§

3-ethyl-5-formyl 2nitrosohex-5-en-1amide
o

(22)
°

2-ethyl 3keto 4methyl

hex-4-enoyl chloride
 0
O
(23)
E

4-methoxy carbonyl-2-methyl
E butanoic acid

(24)
E

2-ethyl 3methyl pentane 1,4diol

 E
(25)

E
4[1-hydroxymethyl]
0

3-methyloctane 2,6diol
E

(26)
E

2,3diethylpent 1,5dinitrile
(27)

°
Butane 1,2,4
tricarbaldehyde
;
(28)
-
}

Heptane 1,4,6 tricarbonitrile

(29)

É 3ethyl but-3-en-2-sulphonic
acid
 IUPAC Naming of Cyclic compounds:-

Priority order :- Principal functional grp > Multiple bond > No. of carbon ring

(1)

2Cyclopropyl butane

(2)

1[1-methylethyl]
cyclobutane
(3)

2-cyclopentyl but-2-ene

(4)

3-ethyl cyclopent-1-ene
(5)

6-ethyl 1-methyl
cyclohexane-ene
O

(6)

3[3-hydroxycyclobutyl]
butane-2-one
E
 É
(7)
E

5-hydroxy cyclopent-2-en
carboxylic acid

(8)
EN
O
at

2-Bromo 5-formyl
cyclopent-3-ene
0

carboxamide
(9)

:
4-formyl cyclopent-2-ene
1-carbonitrile

(10) E
o
o

Cyclohexylcyclobutane-1-
carboxylate
 EN
(11)

3[1-cyclopent-2-enyl]butane-2-amine

(12)
O
O

2[3-ketocyclohexyl] ethan-1-al
(13)

÷ Ethyl-6-ketocyclohex-3-
en-carboxylate

(14)
i.
£

5-carboamyl cyclo hex-2-

ene carbonyl bromide.
.
(15)

Koo Cyclopentyl 3ethyl but-3-1-oate

(16)
E

2[2-hydroxy cyclohexyl]
cyclobutan-one
(17)

E
Et

E
4-amino cyclohexyl 1,3 diol
§
(18)
E

8
E

6-hydroxy cyclohex-4-en 1,3 dicarboxylic acid

 IUPAC Naming Anhydride
O O
If different , then write in alphabetical order.
C —O —C
O O
Propanoic anhydride
OH OH

Butanoic ethanoic anhydride

i.
(1)

Ethanoic Anhydride
 •

°
(2)

o
Pentanoic-propanoic anhydride
:*÷
(3)

Butane-dioc-anhydride
.
 IUPAC Naming of aromatic compounds:-

⑨
S.P + P.P + W.R + P.S + S.S

Benzene X

(1)
i. (2)

2-Bromo-4-Chloro-1
Bromobenzebe nitrobenzene
(3)

B 4-Bromo-2-Chloro
1-nitrobenzene

or
•

(4)
i.

1-Bromo 2Chlorobenzene
(5)

0
*

1-Bromo-3ethoxy-5-Fluro
benzene

(6)
.
0
B

1-Bromo-3-ethyl benzene
# If functional group attached to benzene ring.

S.P + P.P + W.R + P.S + S.S

Single word :- Depends upon functional group

¥
(1) (2)

Phenol Benzoic acid

 (3)

É
Aniline

(4)
§
:

Benzamide
 (5)

E
o
Benzaldehyde

(6)
?

Benzoyl Chloride
(7)

E
o
Benzonitrile

(8)
:
v

Alkyl benzoate
(9)

Em
Toluene

(10)
0

Anisole
(11)

Er
3-Amino 4-bromophenol
B

(12)
É

4-Amino benzaldehyde
É
(13)

E
2-formyl 5-hydroxy benzonitrile
88

(14)
É

2-Cyanobenzoic acid
(15)

É
Bo
o
2-ethoxybenzoic acid

(16)
É
v

4-cyano 3 hydroxy benzamide

8
 OU
(17)

8
Er

4Amino 2-nitrobenzoyl
chloride
EN
OU

(18)
O
↳

Ethyl 3-Bromocarbonyl benzoate

0
(19)

Es
4-nitrosotoluene
E

(20)
o

3-Nitro anisole
If more than 1 functional group:-

S.P + P.P + W.R + P.S + S.S

Benzene

E
(1) (2)
EE

§
E
Benzene 1,2 diol 5-nitrobenzene 1,3 dicarboxylic
acid
(3)

É
4-Aminobenzene 1,2 dicarbaldehyde
É

(4)
É
E
E

2-nitrosobenzene 1,4 dicarboxamide

EE
(5)

E
2-hydroxy benzene 1,4 dicarbonitrile
E
E

When open chain is principal carbon chain??

If functional group, multiple bond , more than 3C-atoms,
:
substituents .
Use Phenyl for benzene ring.
(1)

1-Phenylpropan-1-ol
 (2)

3-Phenylbut-1-en

(3)

2-Phenylpropanal
(4)

É
2-Phenyl ethanol-1-amine

(5)
E

2-nitrophenol
(6)

É
§
O-Methyl benzaldehyde

(7)
É

M-Ethylbenzoic acid
Bicyclo compounds :- Have atleast 2C-atoms.

Bicyclo (X,Y,Z) alkane X>Y>Z

X+Y+Z+2

(1)

Bicyclo (4,1,0) heptane

(2)

Bicyclo (3,3,0) octane

(3)
•

Bicyclo (2,2,1) heptane

(4)

Bicyclo (1,1,0) butane

(5)
iii.
i.

Bicyclo (2,2,2) octane

Spirometer compounds:- Have 1 common atom.
(X,Y) alkane

:
Increasing order (X+Y+1)

(1) (2)

Spiro (3,4) octane Spiro (2,2) pentane

(3)

Spiro (2,5) octane

(4)

Spiro (3,3) heptane

 Common ‘s name

Radical:-

I
CH4 CH3

I
CH3—CH3 CH2—CH3

If more than one different radicals are present, then different prefix radicals are
present, then different prefix will be n , iso , neo , sec , tert etc.

n (Normal):- Radical is a straight chain with free valency .

CH3 — CH2 — CH2 — Cl n-propyl chloride

CH3 — CH2 —CH2 —NH2 n-butyl amine

Iso:- Second last C-have methyl group attached to it.
CH3 — CH — CH2 —Br

CH3 Isobutylbromide

Naming always start from free valency.

r

Neo:- Second last C- is attached with 2 methyl groups.

CH3
neo-pentyl amine
CH3 — C —CH2 —NH2

CH3
Sec / S :- Free valency is present at 2nd carbon.

CH3 — CH —CH2 —CH3

Sec-butyl

tert / ter / t :- Free valency is present at 3** Carbon

CH3
tert-butyl
CH3 — C
Vinyl :- It is removed from Sp2 carbon.
CH2 — CH — H CH2 — CH —Cl

I
Vinyl chloride

Alyl :- H is removed from Sp3 carbon.

CH2 — CH —CH2 —H

CH2 — CH —CH2 — OH Allyl alcohol

9

Benzyl :- when H -removed from Sp3 hybridised C of toluene.

CH2 —H CH2 — OH
Ph—CH2—H Benzyl alcohol
C6H5—CH2—H
—CH2—H
D-
Acrylic :- C— C — G
CH2 — C — COOH —> Acrylic acid
Total C- included

CH2 — CH — CN —> Acryonitrile

Croton :- Same but C - atoms becomes 4.

C—C—C—C CH3 — CH — CH — COOH
→
Er

Crotonic acid
O O
Acet :- CH3 — C — CH3—C—H CH3—C—NH2
→

Acetaldehyde Acetamide
¥
 O O

CH3 — C —OH CH3 — C — NH2

Acetic acid Acetamide

 General organic chemistry

Inductive effect/ Transmission effect

Induction of polarity in the non-polar bond due to presence of a polar bond is
known as inductive effect.
E

Es

is
Eg:- CH3—CH2—Cl
Is a permanent effect
r

Is weak and poor effect

r

Distance dependent effect i.e (Acc. To above example)

Es
is
r

Effects only in Sigma bond crowding

a

Invalid in - bond crowding

E
4
 TYPES
+I effect/+group -I effect/+Igroup

e- donating group
rn

e- withdrawing grouop
Has tendency to increase e-

MT
Decreases e- density in the C-chain
density in the C-chain attached
attached with it.
with it.

Eg:- CH3—CH2—O Eg:- CH3—CH2—OR2

:
:
 CH3 CH3

CH2 > NH > O > COO > —C—CH3 —CH3 > CH > CH2–CH3 >

CH3 CH3

CD3 > CH3 > D > H

CH2 , न ह , ओ , carboxylate , 3 > 2> 1 >CD3 > CH3

-I effect :- Shown by all neutral except saturated alkyles.

HYDROGEN Taken as reference

Inductive effect considered to be zero
 O
—OR2 > —NF3 > NR3 > NH3 > NO2 > SO3H > CN > —C—R

> —F > —Cl > Br > I > OR > OH > C—CH > NH2 > Ph > CH = CH2 > H
-

ओ र 2 >, ना फरहान >, ना िरित क >, ना हीरा लाल >, ना ओमपुरी >,
SO3H >, Cyanide >, Acid >, Father >, Collector >, Beta >, Inspector >, Aur >,

OH >, Alkyne >, Amine >, Benz , ene

Resonance

Conjugation:- If in a molecule /ion , a orbital can overlap with more than one
p-orbital, conjugation is said to be there.

€7
Eg:-

:
Conditions for a compound to have conjugation :->
P-orbitals must be present at adjacent atoms.
P-orbitals must be parallel.
Units having conjugation

1.) Conjugation
¥

2.) (+ve charge ) or - vacant orbital conjugation

±

3.) (-ve charge)

E-

Sp2 hybridised with 2 electrons

f
 4.) Lone pair conjugation
É

5.) Umpaired e- conjugation

É

I Sp2 hybridised + p-orbital having 1

electron

6.) Lone pair - vacant orbital conjugation

:

CH3—O—CH2—CH3
:
In which of the following compounds conjugation is absent ??
=

ñ
N

::
>

I
i

S
✗
 a-
ñ

>
✗
F

O
CH3—C—O
-

s
 • •
•
•
>
E S
E
>
>
E Er
 >
✗
•
E
•
§
✗ S
E E
 >
T
E S
E
✗ S
E E
 it
E
O
CH3—C
O

✗
'
g-

E
✗

✗
In this , N-don’t have vacant p-orbital
 >
E
en
>
E.
 Delocalisation
Take place in a conjugated system.
r

Increases stability of conjugated system.

r

÷
"
If a molecule / ion can’t be represented by single
r

Resonance
structure ,then 2 or more hypothetical structures are
used to represent .
These structures are called resonating structure/ Canonical structures.
.
Rules to write valid resonating structures:-

(1) Relative position of atoms must be same .

i.e Sigma bond must not be broken .

(2) No. of unpaired electrons must remain same.

(3) 2nd period elements must not have more than 8electrons in their outermost
shell.

Actual structure of a conjugated system and its

Resonance hybrid:-
contribution of all valid resonating structures.

Contribution Stability of resonating structures

r
Relative stability of different resonating structures:-
Resonating structure having more no. of atoms with complete octet will be
T

more stable.
Eg:- (1) CH3—CH—CH=CH—O—CH3

(2) CH3—CH=CH—CH=O—CH3

Stability 2>1
More no. of covalent bonds = more no. of atoms whose octet is complete

Bonds will always be same.

:
Non-polar resonating structures will be more stable than resonating structures.
9

O O

CH3—C—OH CH3—C—OH
1>2
 Resonating structures having -ve charge present at more electronegative atom
r

will be more stable.

O O

CH2=C—H CH2—C—H
1>2
Resonating structure having +ve charge present at most electropositive atom
r

will be more stable.

Resonating structure having opposite charge close to each other will be

r

more stable.

Resonating structure having like charges close to each other will be less
r

stable.
 Compare stability:-
(A) O
O
(1) CH3—C=O—H (2) CH3—C—OH

O O
(3) CH3—C—OH (4) CH3—C—OH
 Solution:- 4>1>3>2

(B)
(2)
(1)

(3)
 Solution :- 3 > 1 > 2

(C)
(1) (2)

(3)

Solution :- 2 > 3 > 1

Resonance energy:- Defined as the difference between energy of most
stable resonating structure and that of resonance
hybrid.
Draw resonating structures:-

CH2 CH CH CH CH2
-
n

CH2 CH CH CH CH2

CH2 CH CH CH CH2
→

Es
CH2 CH Is
CH CH CH2

i
÷

:
÷
 CH2 CH CH CH CH2
>
it

CH2 CH CH CH CH2

is

÷
Csi
CH2 CH CH CH CH2 CH2 CH CH CH CH2

÷
÷
CH2 CH CH CH O CH3
:
>

:
it

CH2 CH CH CH O CH3

CH2 CH CH CH O CH3
is

do

Es
]

CH2 CH CH CH O CH3
:
÷
i

'
÷
÷
 is
⇐ . -
-
is
t
i
r
r
s it
Mesomeric effect:-
Permanent polarity induced/ produced in a conjugated system due to
n

delocalization of p-electrons.
Will be a permanent effect.
^^

Strong effect. (Only effects ortho and para positions, meta-unaffected)

Distance independent effect.
9

Two types
+M -M
Increases e- density in attached Decreases e- density in attached
C-chain C-chain

If lone pair is attached on 1st atom —> +M effect

99

If lone pair is absent and atom is attached to most electronegative atom by

multiple bond —> -M effect
Check +M or -M effect :-

(1) NH2 +M

O
(2) —C—CH3 -M

(3) —O—Eth
+M

(4) CN
-M
(5) CH=NH -M

(6) NO2 -M

Me

(7) N
+M
Ethyl

(8) NO2 -M

(9) —CH2 -M
(10) COOH -M

(11) —O +M

0
(12) —C—O—Me -M

(13) —NH +M

O
(14) —NH—C—Me +M
 O
(15) —C—NH—Eth -M

(16) F +M

(17) NO +M/-M

+M/-M
(18) —Ph

(19) —CH=CH2 +M/-M

(20) CH3
No conjugation

(21) CH2—OH

APPLICATIONS OF RESONANCE
Complete conjugation (if all atoms are involved in conjugation)
No Yes
÷
Non-aromatic compound Count e- involved

⇐
[4n+2] e- [4n] e-

⇐
n=0,1,2,3…… n=0,1,2,3,4
Satisfy Haeckal ‘s rule Anti-aromatic
Aromatic
Stability :- Aromatic > Non - Aromatic > Anti- Aromatic

= —> 1
—> 1

÷
- —> 1
+/ v.o —> 0

Identify the following ; whether Aromatic, Non- Aromatic and

Anti- Aromatic:-
(1) (2) (3)

N A AA
(4) (5) (6)

as

A N AA

(Because vacant p-orbital)

(7)
(8) (9)

A A N
(10) (11) (12)

-m
AA
A AA

(13) (14) (15)

-
•
•
A A
A
(16) (17) (18)

•
•
••
N A A
:

(19) (20) (21)

N Because no

A N p-orbital
present.
(22) (23) (24)

A N A

(25) (26)
(27)

_m

N
(Due to angle strain, it
A A
becomes non-polar & no
(Because stability can
overlapping &no
bear angle strain.)
conjugation.)
 Quasi-Aromatic
Structure in which we have to draw resonating structure to check if it is
Aromatic , Non-Aromatic or Anti-Aromatic.

(1)

←
(2)

€
(3)

I
(4)

(4)

•
(5) I
(6)

I
(7)

€
Bond length:-
A > B>A—B>A—B
A—B>A B>A B
÷
Compare C — C bond length:-
(A) (1)
(2)

(3)
 Solution : 1>2>3
(B) (1)
(2)

(3)
Solution :- 3>2>1
(C) (1)
(2)

(3) (4)
Solution : 2 > 3 > 4 > 1
(D) (1)
(2)

(3)
: (4)
Solution : 2 > 4 > 3 > 1

# While comparing bond length within a molecule , check by

resonating structures.

(1)
a

→
O
CH3 C

b O
←
Solution:-
O

CH3 C
O

R.S 1 R.S 2 Bond length

a 2 1 1.5

b 1 2 1.5
(2)

X
O
CH3 C
OH
Y
solution:- O

CH3 C
OH
Stability R.S 1 > 2

R.S 1 R.S 2 So, X > 1.5

Y < 1.5
X 2
1

Y 1 2
Hyperconjugation Effect:-
Nathen and Baker effect / No - Bond Resonance
Here, ⇐
bond overlaps with Sigma bond.
^^

Delocalization of and electrons.

⇐
b
Permanent effect.
^^

Stronger than inductive but weaker than mesomeric.

- hydrogen must be present for hyperconjugation and p-orbital must not be

8

completely filled.
geo
ji
-
⑤

C C
→

— carbon —> Sp3 hybridised

s
 Units which can show hyperconjugation :-

⑦
(1)
C C
⑦

•
(2) C C
⑤

(3) C C C

C- anion can’t participate in hyperconjugation.

In hyperconjugation , when C-H bond is involved , it will be an e- donating
a

effect. Hence called +H effect.

Calculate total no. of Hydrogen which are involved in

i
hyperconjugation:-

(1)

(2)
•
Solution:- 1.) 4 H

88
2.) 3 H

(3)

(4)
Solution :- 3.) 8 H

88
4.) 6 H

(5)
•

(6)
Solution :- 5.) 6 H 6.) 3 H

r
r
If hyperconjugation , effect of a group attached with Benzene ring increases
e- density at ortho & para positions & meta position remain unaffected.
Applications of Hyperconjugation effect

(1) Heat of hydrogenation / Heat of hydrogenation of Alkene

H2/Pt
C C C C + Heat
(Always exothermic)

HOH No. of double bonds/ pie bonds

88

HOH 1
Stability

If bond is involved in resonance , then stability will be more.

 Compare HOH
*

(A) (1)
(2)
E-

E
(3) É
Solution :- 2 > 1 > 3
(B) (1)
(2)
¥

É
(3)
I
Solution :- 3>2>1
(C) (1)
(2)
I

ET
(3) (4)
E-

É
Solution :- 1>4>3>2
(D)(1)
(2)

É
OÉ

(3)
FEE

(5)
(4)
jÉ
Solution :- 2>4>5>3>1

Electronic effect
Complete transfer of electrons towards one of the two atoms on demand
n

E
of external attacking reagent.
Temporary effect
ra

Strong effect

Case 1
H
C C C C

H
Case 2 CN
C O C O

CN
 Two types

it
f.
.

+E effect

If attacking reagent and electrons

-E effect

On different atom.

r
are on same atom.
Eg:- Case 1 Eg:- Case 2

^
.

In which of the following Electronic effect is possible:-

(1) (2)
(3) (4)

E
(5)
 Solution :- On all except 3rd.
For electronic effect to take place , presence of - bonds is

K
must.

Homolytic

Bond breaking / Bond fission

Heterolytic

§
Homolytic A + B

:
A — B

A B A—B

:
Free radicals are formed.
~
 Factors favouring :- High temperature.
r

Non- polar solvent.

Presence of free - radical attacking reagent.
Presence of peroxides.
Presence of light.

Heteroytic:-
:
A—B —> A + B
Leads to formation of cation and anion.
Factors favouring :- Low temperature
Presence of polar solvents.
Presence of ion attacking reagents.
Reaction intermediate

R —> P
Single step reaction

R —> A —> B —> C —> P

A & B short lived,unstable, reactive
Multistep reaction
quantity formed during reaction

Reaction intermediates

No. of intermediates :- n-1 ( n = no. of steps)

 Minima represents Intermediate
¥÷ whereas maxima represents no.
of steps.

§
 ORGANIC
F-ion

CHEMISTRY
Believe
YOURSELF
 Carbo-cation / Carbonium ion intermediate
a a
b—c—X b—c + X
d Has 3 bond pairs , lone pair = 0
d
6 e- in its outermost shell.
Act as electrophile.
Zero unpaired e- [Diamagnetic]
Used in E1 , SN1 and Addition electrophile.

Stability

Electron donating group +M , +H , +I

✗ Resonance
Stability ✗ Electron withdrawing group ✗ -M , -H , -I

At meta-position , only Inductive effect is considered.

 Compare stability of carbo-cations
A.)
CH3
1.) CH2-CH2 2.) CH3-C
CH3

3.) CH3
CH 4.) CH3
CH3
Solution :- 2 > 3 > 1 > 4
B.)
1.) 2.)

3.) 4.)
Solution

1.) 2.)

1✗ H
-

7 4- H

3.) 4.)

3✗ H -

4✗ H -

2>4>3>1
C.)

1.) 2.)

3.) Ph-CH2
4.)
Solution

1.) 2.)
24th

[R]

3.) Ph-CH2 4.)

[ R]

3✗ H
-

3>1>4>2
D.)

1.) 2.)

3.) 4.)
 Solution

1.) 2.)

[R] [I]

3.)
4.)

[R ] +I
4 ✗H

3>1>4>2
E.)

1.) 2.)

3.) 4.)

i 1
Solution

Less electronegative atom donates lone pair easily.

2>1>4>3
F.)
1.) 2.)

3.) Ph-CH2 4.)

5.)
Solution
1.) 2.)

3.) Ph-CH2 4.)

5.)

5>3>4>2>1

C-Cation involved in resonance with lone pair will be more

stable than involved in resonance with benzene.
G.)

1.) 2.)

3.) 4.)

5.)
e
O

Eth
Solution

1.)
2.)

+I U - I

3.) 4.)
0 +I

e 5.) -

M
O
+±

Eth

1>5>3>2>4
H.)
1.) 2.)

ce

3.)
4.)

ome
Solution
1.) 2.)

1✗ -I

3.) 4.)

+M 3 ✗ H

+I
0 Me

3>4>1>2
I.)
1.) 2.)

3.) 4.)
Solution
1.) 2.)

3 H 2 H

:
•

3.)
:
1 H
4.)

0 H

1>2>3>4
J.) 2.)
1.)

3.) 4.)
Solution

4>3>2>1

At meta position only inductive effect

K.)
1.) 2.)

3.) 4.)
Solution
1.) 2.)

+M , -I +M , -I

3.)
4.)

-I

2>1>3>4
L.) 1.)
e
2.)

Me

3.) 4.)

e
Solution

1>4>2>3
M.)
1.) 2.)
2

V02

3.)
4.)

02
Solution

3>2>4>1
N.) 1.) 2.)

CH3 CD3
O

3.)
4.)

CH3 CD3
Solution

1>2>4>3
+I : CD3 > CH3
+H : CH3 > CD3
O.) 2.)
1.)

CH2
3.) 4.)
Solution
2.)
1.)

4✗ H 6✗ H

4.) CH2
3.)

Resonance
Aromatic

3>4>1>2
According to Bredt ‘s rule , sp2 hy C- can’t be positive.

Conditions in which sp2 hybridised carbon can be positive:-

Ist case-> x,y,z -> Bicyclo compound , z = 0

" "
-

2nd case-> If atleast one ring has 8 atoms g.

Cyclopropane
Dancing resonance
C
Most stable carbocation

Q.) In which of the following molecules resonance is absent

1.) 3.)

4.)
2.)
Solution :-
In 2 and 4

In 1 and 3
Carbo Anion / Carbanion
a a
b—C —z b—C + Z
d d
→ It has 8 e- in its outermost shell.
→ 3 bond pairs and 1 lone pair.
→ Zero vacant p-orbital.
→ Diamagnetic in nature.
→ Sp3 hybridised {if not involved in resonance } and Sp2 {if involved in resonance}

e- WG -M , -H , -I Resonance
Stability ✗ ✗ ✗
EDG +M , +H , +I
 Compare stability:-
A.) 1.) 2.) CH3

3.) CH3-CH2
4.)
Solution

2>3>4>1
B.)

1.) 2.)

4.)
3.)
 Solution

1.) 2.)
7 H 1 H

3.)
:
3 H
4.) :
4 H

2>4>3>1
C.) 1.) 2.)

3.) Ph-CH2 4.)

Solution

4>3>1>2

C- Anion involved in resonance with C = 0 will be more

stable than involved in resonance with benzene.
D.)
1.) 2.)

3.) 4.)
Solution

3>1>4>2
E.)
1.) 2.)

3.) 4.)
Solution

2>4>3>1
F.) 2.)
1.)

3.) 4.)

Solution :- 4 > 3 > 2 > 1

G.)
1.) 2.)

3.)

i.
Solution:- 1 > 2 > 3 > 4
4.)
H.)
1.) 2.)

3.)
4.)

Eth

Solution :- 1 > 3 > 2 > 4

I.)
1.) Ph-CH2 2.)

3.) 4.)

Solution:- 2 > 1 > 3 > 4

J.)
1.)
2.)
Eth Eth
Eth Eth

3.)

Eth
Eth

Solution:- 1 > 3 > 2

 FREE RADICAL
a 7 e- in its outermost shell.

:
a
b—C —e 3bp electrons.
b—C + e
d Zero lone pair e- s.
d → 1 unpaired e-.
→ Sp2 hybridised and p-orbital has 1 e-

Electron donating group

Stability ✗ ✗ Resonance
Electron withdrawing group
 Compare stability

A.) CH3
1.) CH3 2.) CH3-C

CH3

3.) CH3-CH2 4.)CH3-CH-CH3

 Solution:- 2 > 4 > 3 > 1

B.)

1.) 2.)

3.) 4.)
 Solution:- 3 > 4 > 2 > 1

C.)
2.)
1.)

3.) 4.)
Solution:- 2 > 3 > 1 > 4

D.)
1.) Ph-CH2 2.) CH2 CH-CH2

3.) CH2-CH2-CH2 4.) CH3-CH-CH3

O
Solution:- 1 > 2 > 4 > 3
 Acidic strength

H A H A

H A H A

Stability :- A > A

Acidic character :- HA > HA

Acidic strength EWG

Stability of conjugate base (anion)
÷
EDG
Acid - H+
 Compare Acidic Strength:-
(A)
(1) CH4 (2) NH3

(3) H2O (4) HF

 Solution : 4>3>2>1

If -ve charge is present at those atoms which lie in the same

period , then deciding factor will be electronegativity.

(B) (1) HF (2) HCl

(3) HBr (4) HI

 Solution :- 4>3>2>1

While going down a group ; size will be deciding factor.

(C) (1) (2)
CH3 — CH3 CH2 — CH2

(3) CH CH
Solution :- 3 > 2 > 1
Acidic strength % of S-character.

r
(D)
¥

E
ÉE

EE
Solution :- c > b > d > a

(E)

:
 Solution :- b > a > c > d
(F) (a) OH
OH (b)

Br
Cl
OH
(c)

F
 Solution :- b > a > c

(7) (A) Cl
(B)

COOH
COOH
Cl

Cl
(C)

COOH
Solution:- a > b> c
OH
(8) (a) OH
(b)

F
Cl Cl
OH
(c) (d) OH

Br
Cl
Br
Solution :- d > c > a > b

Priority order :- Distance > No. > Strength

(9)
(a) (b)
Ph — OH CH2 — COOH

(c) H2O (d) CH3 CH2 OH

Solution:- b > a > c > d
(10) OH OH
(a) (b)

Me Eth
(c) (d) (e)
OH OH OH

O CHO F
Solution:- d > e > b > a > c
On basis of H

i
OH
(11) (a) OH
(b)

OH OH
(c) (d)

Cl
Solution:- d > c > b > a
OH OH
(12) (a) (b) Me

Me

OH OH
(c) (d)

Me
Solution:- d > c > a > b
OH OH
(13) (a)
(b)

OH
(c) OH (d)
Solution:- a > d > c > b
(14) (a) (b)
OH OH
NO2

NO2

(c) OH OH
(d)

NO2
Solution:- b > a > c > d

(15) (a) OH (b) OH

NO2

NO2
NO2
(c) OH (d) OH
NO2
NO2

NO2 NO2
Solution:- d > a > c > b
Because at meta position, only inductive effect is present.
(16) (a) COOH COOH
(b)

Eth Me—N—Eth

(c) COOH COOH

(d)

CHO F
Solution:- c > d > a > b
COOH COOH
(17) (a)
(b)

Cl

(c) COOH (d) COOH

NO2
Solution:- c > b > d > a

(18) COOH (b) COOH

(a)
Eth

Eth
(c) (d) COOH
COOH

Eth
Solution:- a > d > c > b (Due to ortho effect.)
(19 (1)
(2)
Solution:- 2 > 1
(20) (1)
(2)
NO2 NO2
Solution :- 1 > 2
(21) (2)
(1)
OH OH

NO2 NO2
Solution:- 1 > 2

(22) (1)
(2)
OH OH

CN CN
Solution:- 2 > 1

(23) (1) COOH

COOH (2)
NO2

NO2
COOH COOH
(3) (4)

NO2
Solution:- 2 > 1 > 3 > 4

(24) (1) (2)

O
CH3 — C — OH

(3)
Ph — OH
Solution:- 2 > 1 > 3

(25) (1)
(2)
HCOOH
CH3COOH

(3)
Ph—COOH
Solution:- 1 > 3 > 2
(26) (1) (2)
CH3 — CH3 CH3 — NH2

(3) (4) (5)

CH3 — OH CH2 — CH2 CH — CH
Solution:- 3 > 5 > 2 > 4 > 1
(Terminal alkyne stable than Amino and OH)
(27)
(1) (2)

:
Solution:- 2 > 1

(28)
(1) CHCl3 (2) CHF3

Solution:- 1 > 2
Acidic strength order :-
R —SO3H > H3O / ROH2 > Picric acid > Squaric acid > R —COOH >
NH4 > R—NH3 > Ph—OH > H2O > ROH
it Acidic strength Ka 1
PKa

Base strength

Base :- Proton के साथ Covalent bonds —> Base

—> atom attached should have lone pair / -ve charge
 B + H —> B—H

B + H —> B—H

Stability B > B

Basic strength :- BH > BH

Basic strength 1 1 EDG

:
Stability of anion Resonance EWG
Compare basic strength :-
(1) (1)
CH3 (2) NH2

(3) OH (4) F
Solution:- 1 > 2 > 3 > 4

(2)
(1) F (2) Cl

(3) (4)
Br I
Solution:- 1 > 2 > 3 > 4

(3)
(1) CH3COO (2)
Ph — O

(4)
(3)
CH3 — SO3 CH3 — CH2 — O
Solution:- 4 > 2 > 3 > 1
Jitna easily lone pair donate
Comparing Neutral atoms:- Basic strength

KE
IÉ .
/
:

B H B—H
i
@

B H B—H

-
(1)
(1) (2)
•

CH3 — O H

:
CH3 — NH2
••

(3)
:

CH3 — F
Solution:- 2 > 1 > 3

(2)
(1) (2)

•
•
•
CH3 — CH2 — NH2 CH3 — CH — NH

(3)

•
•
CH3 — C — N
Solution:- 1 > 2 > 3

(3)
(1) (2)

:
NH2 NH2
Solution:- 1 > 2
(4)
(1) (2)

-
(3)
.

(4)
Solution:- 1 > 2 > 3 > 4
H
(5) NH2
(1) N (2)

N (4)
(3)

N
H
Solution:- 4 > 3 > 2 > 1

Lone pair involved in maintaining aromaticity will be less stable

then involved resonance.
(6)
(1) (2)

NH2
NH2

(3) (4)

Ph—NH2

NH2
Solution:- 2>1>4>3
H
(7) (1) (2)
N

N —H

H
(3) (4)
N
N—H

i
Solution:- 2>3>4>1
(8)(1) NH2
(2) NH2

OMe CHO
(3) NH2
(4) NH2

F
Eth
Solution:- 1>4>3>2
(9) NH2 NH2
(1)
(2)
NO2

NO2

(3) (4)
NH2 NH2

NO2
 Solution:- 4>2>3>1

(10) NH2 NH2

(1) (2)
Eth

Eth

(3) NH2 (4) NH2

Eth
Solution:- 3>2>4>1 (Due to ortho effect)
NH
(11) NH2
(1) (2)

NH2
Amidine unit

:
NH
(3)

NH2 NH2
Guanidine unit
Solution:- 3>2>1
NH2
(12) (1) (2)
N
H— N N
N
H

(4)
(3)

N—H

N
H
Solution:- 2>1>4>3
(13)
(1)
(2)
CH3 — NH2 CH3
NH
CH3

(3) CH3 (4)

CH3 — N NH3

CH3
 Solution:- 3>2>1>4 2>1>3>4

In gas phase / non-polar In polar medium

(14)
(1) (2) C2H5 — NH
C2H5 — NH2
C2H5

(3) C2H5
(4)
NH3
C2H5 — N

C2H5
Solution:- 3>2>1>4 2>3>1>4
Gas phase Polar medium

Basic strength Kb 1

i
PKb