nisty

[Link]

Organic chemistry is the chemistry of compounds that contarbon

A MHz
ANY HOT
Ek
Lk Cleo
H
Il U's retinal serotonin
absorbs when we see
me tight Human neurotransmitter

Organic chemistry
molecules has given literally creates
itself as it grows Creation of new
new materials such as plastics new
us
dyes
to colour our clothes new perfumes to wear new drugs to cure
disease

Amoxicillin

gIIF
Antibiotic
to _aIµ 1 0
HO
 IN 4 at AZT drug that treats HIV
OF g
Ho
1
Y
Nz

what are the common features ofthese organic compounds

All organic compoundscontain carbonatoms most

contain H atoms
All the C atoms have 4 bonds
heteroatom
may be present
Other elements

Vital foree
mm theory err
Berzeliusthought that organic compounds were produced only
a and
byliving
couldn't be
[Link]
[Link] of they

This myth continued till Wohler converted inorganic compound

ammonium cyanate into urea

D
NHy Chio mtg MHz
Amm cyanate Urea

Catenation self linking property of an element

c C
I 1
C c c c C
c c c
 C C

Organic Compounds

v v
openchain or acyclic closed chain or
or aliphatic compounds cyclic compounds

v v V v
Ho
Imeyclic
saturated Unsaturated Ideecyclic
n n 4.3 IT
n

v v v v
Alicyclic Aromatic Alicyclic Atom

v v
Benzenoid Non Benzenoid

K At
9 aa uz uy [Link]
Uts Cte Cte Acyclicunsaturated

Utz CECH
saturated
Ctesay OH Acyclic
il l
Utz MHz

Homocyclic
Ed
Heterocyclic
o
Homocyclic
E
Heterocyclic
Aromatic
alicyclic alicyclic aromatic

1 I
 formal charge
qt rs N Q

01 Assign the proper formalcharge to the coloured atom in the

following structures

as air 8 Hµ
b nice o csay [Link]
H
0
d Utz C N e H Oj H f Cte o.O

Methane
C 152252ps G.S
H
I Did [Link]
L t 10
in µ
HIIH c Dar 1B TX CES

4 bonds sp 4 sp orbitals
Tetrahedral 109.50
 Ethane
Cte Uts

n
i Sps
i
F Ethene

E
H H

Ei ads
coffin
Restricted rotation about the double bond
bond allows rotation about C C

as
Pz
for
Pz
5
If
Restricted rotation around a double bond causes a new
typeof
isomerism Geometrical Isomerism

i
left
n
e c
µ
l H k
2 different compounds
with the same
same structure
molecular formula
H
 Stereoisomers

02 Using VSEPR theory predict the geometry of following species

a BHy b CS BH
NHy
lHT HTT
l H
B N B H
H H 1
µ MH Tetrahedral H yH Tetrahedral H
Trigonal
planar

d Bef e H2O f Ily

SE U
F Be F O L
linear µ LH cell 4
Tetrahedral u Tetrahedral
Bent

Writing structural formulas

Dash formula condensed formula Bond lineformula
H H
I
H C
1
c
H
I
c H 415012 412 014 fanfOH
I l l
H H H
a

T
H
l
C
H
l
C
H Hl
l
c c H 415914 412413 naff
I l l l
H Q H H

Hl H H
e c
I 1
c H Utz CtlOH Ctl Not
I
c
1 l
I OH
H O H
H
 Write each ofthe followingcondensed structuralformulas as a bond line
OI
as b guys [Link]
ai
ai oats
b us _cuts 2 a
in at
c
gutUtzULOH 7011
us
d
edge _CHUM
cus
[Link]
e Cugat Claw Uts z
TT
l l
U

3 D formulas
oneplane
3 4 bonds any 2 are in
one is out of plane towardsyou
one is you frm
1
away from away

ad
Fi
LIST HI with
ME
codwards
you u
go H
O
H

ULUBr d 4 Br ud OH
µ DU
 b w following pair compounds
Off Identify the relationship of
Br and Br not isomers
E un IV diff compounds

9 and a agency or a isomers

and piund
Haze Ctfuz
a
H
u
samecom
d Als Gts
aisleI Usace and 9 same compound

al bae des
o
Ut Y
feeIne
and
aj ae argue
CyHs
54ae isomers

R O R
0
ether
to us and
adz Dillerentnds
3kg0 CzH60

A 41392 and sa und II

ague
H H
l F same nd
c EEP and
H T µ g
F f
 Hybridization shapes
bonds FreeLop 2 sp linear
3 SP Trigonal Planar
4 sp Tetrahedral
5 sp3d Trigonal bipyramidal

sp's spa spa dSP sp

J d
edu
f p sp3 sp
eg Cugat
sp3
at
cliffSP t sp3
2

spz
d sp sp o Sp's
sps sp
t c Cte
Ata Ctl _Utz
I l Sp2 sp2
sp y Utz sp2
sp3
91 912
Sp3 yay
spz SP sp2
sp2µ o gp2
ICA CO sp
2 sp2
U 0 0 0
C
a Sf
Spj

Electronegativity sp sp2 sp3

He I I
50 33.1 25 l
Scharacter
 Types of carbon and hydrogen atom 10,20130

C is connected to only one or zero carbonatoms

Aly If
Primary or 10 carbon

i lo
Gt3 Ut lo
p 413 to 3011 1
P I i CH CECH
Utz Utz Utz 1 lot g
H
lo
i Mu 20 i
yo or Quaternary carbon
415cg Utz Utz
Utz
10

0
IUPAC Nomenclature
oicacid
Irefinx Word Root Sultix ol

i
seeprefix primaryprefix WordRoot Primary suffix [Link]
d t d te t
substituents NoofC atoms
cyclo c ane
un
in mainchain c c ene fG
c yne

FuG
5
OH
eg u
Hz 2 Methylcyclopentanol
3
Lutz
Secondary Prefix
Utz Methyl Cates ethyl
R Alkyl eg

U Arturo s Br Bromo
X Halo eg

OR out methoxy 0GHz Ethoxy

Alkoxy q
N O Nitroso

Junior F G
alkylhalide
cooy at U1 Br
OH

f Rules for Writing Radicals

Allege Its Alkyl FR e.g ayUh

ai
CH cuz013

Alkene Its Alkenyl 3q c

e.g G at _as 3912 9 42
nm propene
cugat_cnf

Alkyne Alkyl tee

Benzene
H_phenyl GHS
Phenyl

Primary or n alkyl nanogmal signifies a stchain

i se i
Uy ay ay flea cu n pIpyl 31

Ctf Ctf Ctf Utz s

f Ujala CHECK fam
Butane n Butyl
E Iso alkyl
1 i
t
Ii In 3 Abi 413

415413
i i ctfu 3 cycling 3
n
ayah 65427
Iso propyl Iso pentyl
Iso Igroup Iso butyl
win e

rating
octane
t

Iso octane is 2,214 trimethylpentane

mm mm mm s 3 I

Legendary alkyl Removal

of a
Used
only for 4 carbon long chain as it becomes
ammbigueus for 5C oh
10 20 I so to Remove TH
n butyl
94541441 61 3 41 4 912413
n Butta

24 jaguar
see butyl

20 20 20
913412412 41 613 X
app
Tertiary Alkyl
Three Als groups attached to a central carbon with a tough bond to
the main chain
Cll
413 i l
caster 91542 CE lest pentyl
I
l I
l
Clb 93
 t butyl ortman
zlte
Neo Alkyl
i
Uh 013 i
ay dl 4124 i ch d 24
i l 412r
913 913
Neogroup Neo hexyl
Neo pentyl

Naming of saturated hydrocarbons altar C C

TO select the longest chain

of C atoms
0
2
If no
of e atoms are same in more than one longest chain
then
mowrebranYnuiss

the ed
1 c I

G
C

2 Branches
eqtX
1 Branch

30 If no of branches are also same then use lowest

415,7
tongue

iF 4,5 6
[Link]
aigisc 2,4 5
O Il
e

TO Numbering of parent chain is done from that side which

gives lowest
set of locants
 c
I
I
2 3
c EE5
U
c
6
c
6
I
5
c
4 3
EE2 c
e 2 3 5
2 4 5 11 10

0 If both directions get same set of locants then is done

numbering
as alphabetical
per preference
Methyl
c
I 3 2 u l 7 5 4 I 2 I
6
C C c c c c c c C c c c3 c c
5 6 7 I

guy 35 5 Ethyl
3,5 3 Ethyl y

If alphabets are also same then numbering is done

from that side
of parent chain having its branch at tower number
compleganona
I 2
X I
8 7 65 y l 32
c c c c c
V
2
Ut
3
eg
I
41541
2
413 915
t
91
2 q
4
Ut 6 µVs
ai 34
2 Methylpropane 2,3Dimethylbutane 3 methylhexane
4 Br

N
1.5I l
h
I
z u
5

U U Br U
5promo 2,3dichlon 3,3 Dimethylpentane
hexane
4 Bromo 2,2dichloropentane 6 ethyl 3meothffingpropyl
g
uµx
gNaming of cyclic compounds

A
Cyclopropane
11
cyclobutane
TI
cyclopentane
LI
cyclohexane

EI
Methylcyclohexane
EI 1
k5 y
3

1 ethyl 2 methyloyclohexane
2 ethyl iii dimethylcyclonexane
I

2 3
Br
2 Bromo I chloro 3 iodocyclohexane

T Ice
3ethyl 1,1 dimethyl cyclonexane

All ofthe following names are incorrect or incomplete In each case

draw the structure and name it correctly
2 Ethyl 3methylpetard

3,3 Dimethylhexane
qE
3,4 Dimethylhexane
µy
ex
g [Link]
ptani.Z5iE 6 Methyl 3 propylheptane
 Radical Narine

3 Cet Methyl
48115 Ethyl
KV n butyl
isopropyl

uh isobutyl

sea butyl
Agron
t butyl
4

34 phenyl

mph Benzyl

dice Acetyl

31 vinyl

31 allyl

Mar's [Link]
5,2 O Ue Ut
Ck Cty Cty de 412412412413 µ
I 2 3 4 5 6 7 8 q
4Isopropyloctane i's
4 Isoproyl 212,36 tetramethyloctane
 yl yl
Naming of complex branches
In the complex branch the carts as thebasealkyl

groep and nu isd carthisbond edto

parentchain
ai
9
z
glee 2u Eg ft ethyl 2methylpropyl
Utz

Utz Utz
HqUtzzz yl Gees 1,113 bimethylbutyl

e t
S o s 3 ethyl 5
ft ethyl 2methylpropyl nonane
y
MPHPentd s propyedodecane

s
w y 2
r
win

s
5
Gethyl 42dimethylpropyl s Chaz
tg
[Link]

mm
a
g
 write structural formula
of the following hydrocarbons
of 4 ethyl 2,2 6,6 letramethylheptane

if 4ethyl 2,3 dimethylhexane

µ
116
offer dimethylpzopyl 6 1 ethylprepyl decane

intents
Write IUPAC names of the following compounds

6µF
5
at Tb 3,3Dimethylhexane
2 Dimethylpentane

IF
3
s
dinn r Iz lo
3,3Diethylpentane
n
l
f
3Ethyl2,46 trimethyl s propyloctane

write the number and it bonds in the following molecules

of
µ H
14

IIµ
o y
f
H
I An
t
H
Tokin s

0 25 0 20
IT 6 IT L
 Nomenclature
of Alkenes Alkynes
1 Select the longest chain containing e This need not be the longest chain
in the compound as a whole

3 2
eg
yes ay ay ay de Utz 3 Propylhept l ene
46k
5 412
6 Utz
Utz

2 Givelowestdocent to the c

I
3 415 Dimethylhex2 ene
HIT
14 2

3 foralkynes the chainselection numbering

is done in a similarway
Gt3 z z l
Utz du CEC Utz
4 3 2 I
9 Utz CH C 61 S 4
But tyne y methylpent 2 yne

both c c and c c are named alkenyne

4 Compounds containing

Numbering is done as per lowest set of docents rule

value from bothsides then
If lowest set oflocant rule gives same
c gets a preference over c

I 2 3 u s 6 7
eg avec ay ay ch _ch Ctb Hept 5 en
tyne
1,5 2,6
5 y 3 2 I
at C Uf Cte_Utz Pent l en 4
girl
 s s
eg n l2 z
oz
s s s
4Chloropent 2 ene cyclohexane 1 methyl 116 Dimethylcyclohexane
cyclohexane

I cyclonexylpropene

At least 20 LUMI

PriorityOrder of F G Intf
 Nomenclature of organic compounds with one FI
Longest chain containing the EI and max exam is selected
as parent chain even if it has clers no
of oms

µ 55

t 22 get_Uta Br
g
Ut
e fG
ut Cha Ut I
eg l 6
s
OH
I
OH 2
Utz
Cuz µI
Numbering starts from the chain
terminFF [Link] ke zoom
CER Ufo coff co Ha

suffered y 2
eg s coat

NO 0
2 H
70413
I
t Nomenclature of polyfunctional compounds
1 When an organic compound contains more than one F G then seniorEEL is
selected as the primary Fa while other groups are treated as subs
Ituents
atoms
M [Link] G similar Millpond Max no 11
Maxno of ants lowest I ht alphabetization
 when chain terminating F G is directly attached with
ring then ring
is taken as parent chain and special suffix is used for this fG

CHO Carbaldehyde
Coon carboxylic acid

d X carbonyl halide

cook Alkyl carboxylate

CONH Casboxamide
CN carbonitrile

a
6 1 Cleo COOH
g [Link]
eg
u if 4
1 I l
s l l
Cyclohexanecarb
aldehyde cyclohexane
carboxylicacid

C H5 2 oxo cyclohexanecarboxylate
Ethyl
4
46

examples
Somemore
um
special Topic Bicyclic compounds
Two rings with no common atoms

5 ketone is highestpriority FG and phenyl is

6 substituent
2
3 Phenylcyclohexane 1 one

Benzene is the parent

ringsystem as it contains
more C atoms and has 3 substituents
y g no
NO I cyclopentyl2,3dinitrobenzene

5
6 y

G I 2 I 2
s
s l 2 z
i 2
2
y
s

Two rings with one common atom spiroring system

Use prefix sepir instead of cyclo
I 5 f
Numbering follows the sheath first passing
2 y n through the spirocarbon and around the
z 8 SEND ring
Spiro 3.47octane

Spiro ring systems are always numbered smaller before larger and
numbered in such a
lowest docent
way as to give the highest priority F G the
l 10 9
O

n
t
y
2
3 EXT71
u f
913
5 I Utz
 Spiro 3.4JOct 5 ene 7,7 Dimethylspin14.57decan 2 one
5 I 6 I
y
61 2

I 8 3
a s
g lo U

2Chlorospiro13.43octane 2 Methylspiro 4,5 deca 1,6diene

at G 7 7 6

5 ChloroSpiro 2,47heptene 6 oxaspiro 4,57decane

Two rings with 2 common atoms resedringsystein

cu Bridgehead
Et Eis
atoms
fused rings Bridgdgerings

The longer path shorter shortest

In fused rings the shortest

path is always a zero meaning zero atoms
b w the two bridgehead atoms

Numbering slasts at bridgeheadatom

Bridged Ring system
Two rings that share more than 2 common atoms
Numbering starts at bridgehead longer path shorter shortest

i
 Isomerism cuts cnH

Existence of different substances with the same molecular

formula is called
Isomerism

v
v
Structural stereoisomerism
Isomerism nm

Isomers with diff structures Isomers with same structure

but different arrangement
me
inepece
chain Isomerism
position Isomerism

functional Isomerism
Metamerism
Tautomerism

chain
They dine in the
or
MEILI seizin
side chain
Have same nature
of Louis EE multipkbend or substituents

Utz
eg he and 1ay u4 U 3C
Butane

2 u 6

3 5
and IN
I uc
6C 3
Iou
 n i y n

E and
If I 1 and
Eola

Posin m Isomerism
branches
G multiplebond
TDitter in the position of locants F
I should have the same size main chain and
of side chain
v same nature of locants

But l enl But 2 enl

EI E
l ia
9 me my

ve am
a
0
Ed
ortho
II
meta
EHpara

2 4 2
y

µ 5µm goon s
goon

0110

3 Functional Isomerism

Diner in
[Link]
0 H alcohol
Hoo
Ut
Ugo Ether

z
 N
Formula functional Isomess Cutts 4
CnHan Alkene Cycloalkeine
415C C 913 Utech Creon
Cn Han 2 Alkadiene Alkyne cycloalkene
Han120 Alcohol Ether
µ
CnH2nO Aldehyde ketone oxirane ay E Ut saz Utz I H

ChHan02 Acid Ester hydroxycarbonyl I

10,20 and 30 amine
Utsav OH oh Eo ai

are FI
ai as
UtzUtzUlzNHz 10 amine µ
Utz At Utz 2 amine lymb famine
x Utz

2
c c c e MHz
c c
IMHzE
famine
Y'H2 MHz c C N C C
Dec E zoamine
famine c c C
2 3
c C C NH c
2 IN
c Nu c I
a

B PI DRE F'I feats P I

A
C C I Def RI
A
C I Dd G FI
A dD
PI Didi fI
C D
4 Metamerism
Ditter in nature of alkyl group along a polyvalent group
Chain or position isomers are not considered

c C O C C C
ether c c O c
2 I 3
2

Amine c c N c c
C N c c c
i
c c

Ester
Aejaz o al
a w Ut I O 412013
a

NH Ut NH Cty's Metamets
g 415412 415 I
in w t

5 Tautomerism Keto end

the location
Aketone and end diller from each other only in of a double bond
and in the location of hydrogen

Tautomers are isomersdiltering only in the positionof Hatoms e Thecarbon

skeletons are same

Eg

X H on carbon atom
Requirement sp
acidic or basic medium
 write the structures
of proton tautomers of the following
oxime N Nitroso

f MAN lol I
H
b 413 42
ph I pµ
OH
C k RN f o N OH

Bare
0 OH
f 13 Ny I 92 N
o

et
Phyllis's
H
Ph 91µg's PHIL 043

Draw all
Eythem protontautomers ofeach ofthe following structures and arrange
in the increasing order
of their end content
a NH2
by 1K so
e
info
NH Tt
I I 9 OH
l
IN
Kiko
I
TT'T OH
H
aroma_l

Cmoststab6 [Link].e
L
01Identify the relationship btw the given compounds

oh
µ
f and chain isomers
5C 4C

It
tic
and
1 3C
04
chain isomers

Hot and hot Metamers

da 1 1 and 0 functional isomers

a hydroeyketone

et and
12 Ringchain isomers

f
ME and
ooo
Not isomers

and I Metamers

Identify the hybridization of all carbon atoms in the given molecule

sp2

[Link]
s.EEp2Eo
oosp3sFB Vkc
sp N
p
sp
 sp

are possible with molecular

Hffmmueaany Inquires of cyedalkanent
band
2 double
1 triple
DU Ct 6
HtX2 821 2 Iringedout
O O
H
ID 0
D
De Du
de write the IUPAC names
of following structures

H 4102

ldeI
a de
f
I Br

b
µ
r
I meagleehenyl

vinyl Of ethyl

MEET 2017 2 Methyl 3 oxohex 4enal

G
µ
µ
5

foot ed 2 1172004

µ INH 3 aminobenzoicacid

Ezel 0
method
I
a

42 lit zoos 4 Methylbenzenesulphonic acid

F
2 l zoos hyl up
g
r tes

which
ofthe given compounds can exhibit tautomerism
H
NEET 2015
Ix

[Link] s a 1
I CI III

Drawthe structure 37 5Exocyclohex 3Inecarbonylchloride

of
did
2
6
5 410
0
Fr fundamental concepts
in Organic reaction Mechanism
A B C
Ee ee
AHacking
Organic Molecule _s Intermediate Product
mm
Substrate unstable
or
leesstable

AAPB th t B
Free radicals
Bond fission
1
s A B
y A t B
O

I cation anion
MoreE N

Nuundegpkines Eyck peu having an Epg available for dLation

nucleus ing
we charged a Br I Ro OH SH RCW al

Nui
Neutral
µjj Jing ROH KiHaElHz Rs't
R3P LiAlHu NaBHy RaeLi RMgX

Nui attacks on electrophilic

sites
Et
e deficient species that are attacked
Electrophiles
mm un by nucleophiles
El ing ut ut ri 02 1 3

pug 502 SO BHz Allez Bfs

isn't tab incomplete octet
NHU empty
an
 which of the following species behave as a nucleophile
an electrophile
both
Neither
a Ce Ol g Brt 20
M City
b 1 60 10
h rest 20
O
Cty at 41
i
Snay 20
c Ht 20
5 0NO
toEt
d AlBr
k te
q
O H
E Os
e [Link] 01 H H Need
l Nu
f Bell CltCEN
0 st s
M Cty at 412 45C IN

Movement
of e and use
of arrows
ATPB A B
eg
A At B

highe density low e density

A 0
c c
Nui E
It Eto
 Electron Dinsphaummut Effete in covalent Bonds

Permanent
Tarang
Electromeric effect
InductiveEllect
Resonance Mesmericeffect Inductomeric effect

Bondresonance
Hyperconjugation No

o Ipo1 0.01
InductiveEAect
got ss St S is
C e e 2 e withdrawing group
ti moreE N thane
t Ewa
4
Heat sss ss s s1
C C Cece Z 2 is e donating group
soft I f DG
500 IT less E N than C GII
5 Its a distance dependent effect
Ld e density due
to E N difference
11 Its a partial a
permanent displacement of

I groups e RNR ER H NO so R CN
mm
Clio COOH f U Br I OR
sp sp2
H C Ctl MHz CHg Cte_Uz H

I groups E Coo c
Chae okay
um
Ctl D H
Jerry March

I L Finar
 eg É past coon

[Link] co

Resonance
sometimes all the properties a molecule can't be represented by a
of
single structure but by two or more structures

There contributing structures are known as resonating structures

or canonical forms

Ép i k

o F y g o
go o

Hybrid

Actual structure is represented by a hybrid of there canonical

forms
Resonance is a hypothetical concept and resonance structures
exist on paper
only

Conjugation charge charge

Red clad

asthma I a a iii

y
 Update Iz ar ar

afaik er as as

tears an

a
EI E FI NI et
It

Resonance P E difference btw the most stable resonating structure

Energy
resonance hybrid

Hybrid
g

retire
EI
Benzene
EI
Naphthalene
EI
Anthracene EDIT
36 61 83 phenanthrene
91

EID E E Ei
Pyridine furan Thiopene Pyrrole
28 16 29 22
Rules for writing Resonance structures

All the canonical forms must be properlewis structures

octet must not exceed period elements
for 2nd
Ex Hex
He can move e
only No atom should be displaced from its position

aesate
ay ay ai _ai u
IIE at 2

AM atoms taking part in delocalisation

me must lie in same plane

8 e 88
All canonical forms must have the same no
of unpaired e
if conservation
charge

if The energy of
the hybrid actualmolecule is less than the moststable
canonical form

All canonical forms don't contribute equally to the actual molecule

More stable structure greater contribution to hybrid
A B C A es B
8 10 10 8 8
Drawing Resonance structures

Relative stability of canonical forms

octet completion gives more
stability
a o ae e are 8 ae
More stable

te te gte
ge
structures with more covalent bonds are more stable

9
Me
412 41 41 41 a 41 41 41
a
More stable

chargeseparation decreares stability

0

ae99 u custody
has stable

structures carrying re charge on more EN atom

stable
re charge on leis [Link] atom

Pfai9 ai Fear
[Link]
Morestable
I Write the contributing resonance structures and resonance hybrid for
the following structures

as Aton Age If on
b
ÉÉÉÉ At At
a
IIF e
ie
EET
d
Ey Ed
e cus II a ash
Colet

EYE 8150 off Eto Eto

E EE
Identify the more stable canonical form among the following pairs

as E age at IIe
b
ay Yo e as
É H

C CH I CEN e a a ni

d
II III
e Ma
M
2

MHz MHz
 can't show resonance
which of the following species
Q
a
I
b
Ey II as
Ej
In which of the following first structure is more stable than the
second

a
Ey creo a apai o

b Eez o cu e cha É Ch

c
Cha Che Na e H Ch MHz

d che cha a one I

which of the following structure least

I stable
of 1 Methoxy 1,3 butadiene is

a
a a a a ok b
ago in a 8h
c
E ut en en o as as apai É É at

Isocyanic acid has following resonating structures

H N GO e H int c 8 e H EC É
I I III
The correct order is
of stability
Resonance or Mesomeric Effect

Fatty produced in the molecule by the interaction

of 2 it bonds or
btw a it bond and a lip of é present on an adjacent atom

This is a permanent effect and not dependent on distance

Its transmitted through
In

IR or In Effect when thegroupdonates e density to the conjugatedsystem

eg O NH Nar Nra oh or in E R s o I R Ph
f d Br 7 I 7 NO

no I g g
o R
cold cook s cont coo

r
 r
EFF
Steric Inhibition SIR effect
of Resonance
In case 1,2 disubstituted
benzene
if the substituents bulky then
are
of t benzene ring
due to repulsion the group goes out of plane wi

Due to this the conjugation btw benzene the group is reduced

ring
or prevented
goesoutofplane

887
É
I
Ets ep is notinvolved
conjugation
for
in
is available
sharing
y n I
It Morebasic than

II aniline

Write é density order in the following compounds

IIF
a
IIA B
Ey Ej
D
good's
C E
F It is delocalisation of que cloud with porbital
Hyperconjugation
Also called Mo bond Resonance or Baker Nathan effect

x H at sp3carbon w rt D 8 or
Requirement presence of
l
c
413
eg des lat bish 14 ch cu
I catch34
3 4 6 Cee H

x 0 x x a a

41521 Cee
des GH 2 41541512
644 At 2411
1211

a In alkene

µ eu es te de AE Ho an 48 µ a
g gae
Totalstructures It x H

In carbocation

a
12
A Ho c ie
Iff
c In radical
H H
HEb a ie c
of
I l
te te
d In Toluene Ht

EI ETE Ish EI
I

structures
stability of alkene x No
of Hyperconjugative

Igad
1244
Iec gam
as
seas
641 Pieta
pay transalkene
in
Yigal create
3211
after
zero RH
cisMane

Bond length is also affected

1

I okay a
ay an as y
62H
H
I
I
Ike ago Kae ai

af I I
2 more
5 more
Negative Hyperconjugation when strong Ewa is present at a c

f f e density is donated from

k 12
H a
filled it or
p orbital
H into an adjacent 0
0
a orbital
Ix 41,011,1412
501 ainga
CI
to
E Ph at t
zero X H
Cle at at
624
413 913 413 0
I UGH
415C 41 915deal 41 5C 412
1
at 3411 9411 at an X H

In hyperconjugation there is overlapblue

a p and p orbitals b p and d orbitals

c and p orbitals d S and p orbitals

the following alkenes in the order stability

Arrange of
4411 10211 644

III II I
II I
II
a
o o
II

b
I
1 1o a
II sit II

I II III II
10211 244
 The correct decreasing order of e
density in aromatic ring of following
compounds is 0
initial
as EojEIms bs
oj Moderate I
strong
f t 1at
c d b a

select the correct statement about this compound

A
Noz a all three C N bond length are same
SI
b all three c N bond length are different
t NO IT N Cs N Cz N
02 Br i d c N Cg N Cz N

The decreasingorder of e density on the ring is em I

4 43
43
1
NH 43
M
go
th M
81 l
A B C D

D B c A

bond in the following compound

Decreasingorder
ofbondlengthof c
194
r
ICH 3,1113
e
s
afp q r
b r 9 P
10111
Yq c p r q
1 412 d
U's yall q r sp
Electromeric Effect Its a temporary effect operating at the demand
of the attackinggent

c
A
A ETO away ago i carbocation
Cte 41 612 E
1 2

cuffee u at
aye gocarbocation
E

Aromatic Non aromatic and anti aromatic character

cyclicstructure with continuous conjugation

structure must be planar 41Te She
Cent2 IT e Un IT e Hackel's Rule
Aromatic LITE 6lie lone Anh aromatic
stabilityorder Aromatic Non aromatic antiaromatic

g ae T

EI EI E Fil EI H

EEF Naphthalene Not planar

man
aromatic
Aromatic Non aromatic
Pyridine

FI E E
Gue f
[Link] eEahnmmn fVdichTromalicn emaeic Amalie
 une

fi
4He
is
4He
4.7 EA ya
Q The following hydrocarbon has unusually large dipolemoment Explain

Tie The

Classify the following compounds as aromatic non aromatic or antiaromatic

Iy
a b as I as
no

t as N
ETI
JEE adv
20
Among the following the is
no
of aromatic compoundis

EI ES EI EI EI EI
 Reaction Intermediates Reactants
MONProducts

Carbocation a carbon intermediate which contains 3 bond pairs a

positive charge on it Ht
Ctl
M Ulyt Uts
carbonium ions
meso called carbenium ions

E soft Ito
est r Nui
E
i

sp
CE
soit
empty porbital
e in octet
e deficient species with 6

Preparation
1 Heterolysis of a covalent bond

45 Ef x

of alkene
2 Protonation or alcohols
that I
5412 412 I carbocation
Uezcte [Link] T
I 2
at 2
Cugat de 20 carbocation

[Link] aes
aeaEfo.I Es ouEafIIaea

3 Thermal decomposition
of diazo compounds
R N NX
D
R t Ng
U
 Because carbocation assumes a planar structure its formation is inhibited
in compounds which don't permit the attainment of a planar
geometry as in bridgehead compounds

carbon
Bridgehead

µ X 7
L
x
dispersal ofcharge leads to stability
stability ofcarbocation Hf
stabilized by
th and hyperjugation effects
Greaterthe no higher the stability ofcarbocation
of EDG
St St St Dh 1B
cee at H
e.g great q St II
StCtl Ub A B

re
a
III II'm [Link]

It y CI
[Link] pC
1
[Link]

MY Utz Utz uz
k il k k k
I
I s
l l i l I
Tenzyl I
carbocation
Stabilityorder ma
UI
g
Phi ph gin Hsbc Ph UE Eh
substituted
Tropylium
I a BeIyl
t
allylic
cation
To Caedaut assai tune
go to

ay U a Cte c
A Uk
Benzyl vinyl phenyl

t Phenyl

Cyclopropylmethyl cations are exceptionally stable

D is a D Ed
Bent
orbitals
DIET
Rearrangements
R
of carbocation
H

II I
1,2 shift

Igf
H r H

R
carbocation
10carbocation

1 Hydride shift µ
fth Hydn I

459GHz
H
lo
fk Ues
fo ut

30carbocation

27 Methylshift

Ft iz Yb
 tUe
Clegg
413
Uts methyl
shift
aerial ab

2 carbocation 3 carbocation

III
20 carbocation
Ete
z carbocation
Ring Expansion and
so

ft Ei

in I

me

4
Ring contraction
43
Hen Uts
FI
i UE
Tt D

F DYE
or
[Link] more stable

Rearrange the following carbocations into more stableform

Gf
wfsaes
a at9 ae

[Link] E
b cee
ay aes ab
Cee
cirques
[Link]
in
u
i EE
 As a
5 shot H s
20
Gt3
d Uts at we aus
Utz
UG to go

2 Carbanion A carbonintermediate which contains 3 bondpairs and a

t negative charge on it

E
QE E
tetrahedral
sp3

e rich species with a complete octet Can act as a base or nucleophile

formed during heterolysis qM_Z
of c u
z

f stabilised etc
by the presence
of EI eg I 11

[Link] cQg s a

y N0a More stable

u

anti aromatic
u n
x aromatic
µable Unstable
 stable

3 Free radicals There are carbon intermediates having an odd e

I formed during homo

lysis of covalent bond

I Neutral

incompleteoctet e deficient

9 Is aci Alkane
stability is similar to those of
carbocations
t
Q Arrange the following in decreasing order of their stability
T YI YI YI
a a
1 3 a

XY IT
b 3 231

EI EI It allylic
IIF s 2 1

II 3727471

e Franco Teach fugato heater

cu 1737432
LEI FEI TI 2 173

Titi EI
Tea Tcf
Benzyl

[Link] gig
anti FI
aromatic
I
20
É 20

2747371
 0 0412

lem
i 1
CI

Cl
I M
12
2 7 I 573 4

which the following species doesn't have equally contributing

of
resonating structures

a q theatre 12 c 149
I I o
pu
p Ut Ut 412
415 0 412 41 612
Least contributing resonating structure nitroethene is
of
Moststable
a
Uefa N
o
b day Ee
Eff
Ey UE NOE d
gtte
N0

d The correct order

of resonance energies of the following compounds is

e e
47 4 o to Ey
p p p
 i
4 2 I 3

i
 Problempracticen

Qt Rankthe following sets of intermediates in increasing orderof their stability

a Cts cIPphn 541 Ph Cll Ct 412 1402

0 0
b CoHg p NO Cotty Pitts costly p Cl 411450

AI MI FI FI
EI EI EI EI
e
ay
DP
H outs I NHL 81 9 414

02 whichamong the following is a stronger base and why

442 41112

Fil or
Fil
YNO XYX
NO

3 Discuss the mechanism of following reactions

I
a
 x w

b 115 992 6154111 t Al 41 41

04 Discuss the following observations

a C A bond in Uefa Cl is stronger than in Cheju 4
b is
cuzshe stronger acid than Alstott
c Benzenesulphuric acid is a stronger acid thanbenzoic acid
d An alkyne is more reactive than alkene in catalytic hydrogenation while
reverse is true
for electrophilic addition reaction
05 Unlike naphthalene azulene have significant zwitter ionic characterand
dissolves in aqueous acid Provide a mechanistic explanation

is e