eneral Orqanic Chemisty

Reactant Reagenl, Tokrmidiate

product 4 bypreduchvc

Bond Lisien er clecva ge (3 types of intermedl iades)

+ A

Carbanion Heterolyhc
deavage
+ Ax
Carbocatión

Cish=hook
A
fatl Homolyhc
hadical cleavage
 b+)TT

Elechron Displacement Effects

|. Inductive elked (Perm anent )
operate to o bond
- pantial change olaveloprsn t
Can be rglected asts 3rd C atom
dopends on distance
’non polay
CHa CHa

Hence
polor ds kance dependen t

a)-I eedt
G
-I EW G
 5) + I ttect

+I EDG
eletron

donatirg ups
-I 2eries with power C( Trick)
-NO, > -SO, HH )-CN
>-NH, cyana
-NE, 7 -NR, y-SR,
shahrukh na himesh
Salman
na om puri
na farhan nariik
U>- Br I)-OR
2-CHO 7 -COOH > -F)-colletor heta
inspecror
ali Ki (ar meln father
yOH-CE CH) -NH,-Benz7ene
nahi hai benz ene hai
calcohel akyne

+I Series

-N 0 - C o 07>3R2'R >l°R
)-CH,

2) -T > -D > -H
 Co

Applications

) To compat auidic strength arboxylic

acid and alcohols

-coOH -(o + H
Cinion

Skbility f anion d Aidic Styeng th

o CooH.
is
chaugt
Shold bevecuce d

which car be don

by -I
- groups
+T ’-co 6
Stobithy ‘ Stability
aucic Strengb audic trerg th
of c00H ‘. o coo

Condusi on
Aidic Strergth d-I ellcuts

Priony: D>N>
>P
distanu nunbr povur.
Lample Questions

Compone acidic trength

D, ’oOH CT,coOH
a) CH,cooH
TD> H

audic streng th

Ans: <@<O

b) coOH

distana â

cooH

distane >

has m in nn bn. (-I)

Hene
 COOH
d) cOOH
(OH
-I

alky

cooH
-T Sisy
bon
cooH

CoOH
COoH (oOH

CH =CH,)
TcooH
2. To compane stability in krme diotes

cbocahon

Stability ‘ than change s houldl

be dlereose ol

+I efect
Stability
Carbanjon

ng chong
&tabi}i hy,
to at tain showd
change
reducecd

EW)

-I eet

o carbanion

stability of u adi col

thot oh cavbo cati on
bample Questons
cormpane stabily CN
NO
CHs
+

2) >

me

fre radical behaves li2e Carbo cahionf )

+I is qood

cistnce wire
dÜnce mumben powey

Aweakest)
will
highest
stabili ty
ken carbocali on,
 2. Hyporconjugaion
OCCUrs Alkenes
albeno
Carbocahioni free
radical

conditions
d-C, shoula be sp' hybicited
) Centain (a-H) ot leay t 1 d-H.
i)-C should
Case I in abocatian
tvuctues = No. of d-H)
Ne. o Hyper.cojdgativt.

ldH HCS= 2
d-C

-sp
3dH
HSe 3
 Ctavbocahon H.C.s)
Example Questhons Hyperconjugatt
Q free radi co luptr
Structrs.
find fotal no. dk H.c.s
If tnsteac
Lnvolving C-H bond rcohing + charge
each Q.
R H
yoe pt an e
(free rad ical )
hoH.C.S will
remairn Sane

So. carbocaion
(3
2 free rodical
concept /s
Same

|hCS =3
|HCS FG i.e,
ho o o H atong

JHCS =6 HCS 5 |

H +

HCS- 8
 Case Tt: nIn Alkenes
H

H C cH = CH,
H

but this Caot have 5 bonds.

bond e sbif to
H- C CHCH CHy r is weabn
Hence hat
breahs )

H*

H-C=cH- CH,
bonds will
the 3--H atams
any
will fom 3 H.c.S.
this way
break.

IL: So et vacical
Cace
H

CcH,
H--cH, <’ H-
H
Homolytie
Jeavage H
H°

H-C= CHa
H
3-d-H bonds oil) break
this way, aany of the 2 fo2m 3 HCS
 ample Quest ns ( no H.Cs in Al kenes)
Cinvolving CH bond bredlkir9)

H.C-s= G

HCS =3
circde he al kenes then Count direct aC ato attacho d
& Sum u all d-H ato ms.

(no bond ssonance)

Applieation d Hyperconjua ation
() to compa
compae stabilty V. Imp.
Carbocafien, hue xadi cal Lalbuas Hyperconjugation
alkong ellecd > Inducdie
CHH, Efect
no. HCS
Shabiihy (involving C-H
bond breakirg)
Example Qyes lions (compane stabilihy )

HCS=9 HCS:6 HCS 3

ho2 strctures,
H.CS comes same
& check Jncuctive
then we

H.C

Same,
9 fo Erouctic

carbocatio, + I is favsuabe,
ifeet is not. woull be
weakst - I SBabk,

2
 3

HCS
HCS 2
2

length
To compane bend
bond lenyth
C=C CEQ baciss.
bord leng th
bond energy
Ht

H
H

2 1
H
= CH
2
,
|3 H

enpeced
C,-Ca isis shorler thon esepeded
C-C is largn thun
Z Resonance
Aingle dewis struuchue is incapable
- hens molecule then cwe
explain pop
pop f% a called
need tw mole&truct they
¿truct es ( (R. S)
pes eratig
- RS oe hypotheticsal the actual
(Resoranco Hybricd is
RH
structwe) i mort
&e RH is
RH ha
ha lowest enng
dont fouch
8table
0 bordy

O-C-o

R. H
wl
-2
-2
 cOndi tions ko cempeunds to how eloane

atons must be plane

al pantici paing n

v.V.Lmp
N
NeNO
NO
ti) conj ug ation
) X= y -

22) XX=y Z
3) X =y- z
X=y
)X = y - |
5) X= Y -Z = W

Types o conjugato ns
)x= y
LP B
BP LP

eg: CCHRH,
-CH=NH,
2) X=Y-Z
LP ’ BP
BP ’ LP

y"
Y=Z
-
CH, -CH =CH
CH, CH-CH,
3)x y
BP BP

CH, = CH CH,

4) X= y-{
BP BP 70 in tonulusion,

Hy CH = CH
 5) X =Y-Z=W
BP’ BP

BP LP

X yzw
y=yZx-Y=ZW
Ynove fowaldsQ
atom

CH,- CH CH eletrorgatire( pu
e)
cH, = CHHECH,

Exam ple Questions (Draw Res onating Structures

 NH

Jo-H

CH-o CH-0
CH FO SH
P
OH
F

1
+