REACTION

MECHANISM - 1

REACTION INTERMEDIATE

Neeti Mishra
M.Pharm (Pharm. Chem.)
Ex Assistant Professor
GATE qualified
10+ years experience
NEET, IJSO, BOARD
Educated more than 10 thousand students
 Reaction Mechanism

Concepts-
— Bond Cleavage
— Attacking Agent
— Reaction Intermediate
— Electronic Effetcs

—Types of Reactions
1. Addition Reaction
2. Substitution Reaction
3. Elimination Reaction
4. Free Radical Reaction
 Clearge
-Bond
says
fission
Homolytic
2 . uv
↑
Heat/light
:, +
O

A B > B

Peronide
- Free racticals

C .

Heterolytic fission
+
:3-
(Ai
+

A:B -

+
>
-
+ B

(Reaction Intermediates)
Cartocation
t

Cartanion (A)
 (6) Nucleophilic reagent or

Nucleophiles
(i)
Negatively charged nucleophiles

H- H R <N -X -R , RCOO
, , , , , ,

NH2 SH
-

(ii) All Lewis base which contains lone

pairs The
or

He R-H
10
,
R-R
1
, H3
,
R-NHc ,

R ,
Che = CH2 ,
CHECH

(iii) Some atoms chonates e to the substrate

NaBFy
*
*

R X
Mg LiAIH
- -

&
y ,

& L

CGrignard
L

↓ ↓

Reagent] good reducing agent

 .
3 Resonance
OR

Mesomeric Effect

If a
molecule can be
assigned two or more

structures ,
none of which is capable of describing
all the known properties of the compound #
then

the actual structure is intermediate or resonance

these structures
hybrid
-I
of .

= -c : -

+
R effect >
-

to donate e-to
If substituent has
tendency
the double ford
.

U Br
-NR2
-

-NHR
-

,
-
OH -
OR ,
-

NH2 ,
,
,

,
- I
1 +7
S 1 -
7

CH- <+: CH2

.

-Ch = Ci
CH =
-
 Hyper Conjugation
4
.

(Baker o Nathan Effect]

The between the electrons of
interaction
# systems and the adjacent & bonds of the

organic compounds
substituent in is
groups
called
hyper conjugation .

eg-
Ht
H
I
H-C-CHCHH-CCH
12

it H

>
-
Since there is no bond between the x-carbon
atom and of the
one
hydrogen atoms
,
the

hyper conjugation is also called no-bond resonance

 Carbanion

which-ye
Carton
charge is present .
>
- on

>
-
Complete octet

bonding
e.
Has
>
- non

Sp3 1070
>
-
,
Pyramidal ,

Stability < No of I
groups
-
.

a
/No . of + I
groups
Ydistance
& from -I group

Stability order CH3)1072) 30

 FREE RADICALS

atom
group of having
an
>
- or atoms an

unpaired
"
electron .

These
during homolytic fission
produced
>
-
are

A th/
: B
Heat
it is
They reactive
>
-

secondary
are
very
->
Free radicals can be prima ,

or
tertiary .

H H It
HzC 3
H
&
L - &
C
Hz c T
[
H3
C Co
H3
- ⑳ .
C - Co [ -

I
it p

methyl
H

10
H

20
↳
 CARBENES
-

>
- Carbenes are neutral species having
a carbon atom with two bonds

and two electrons .

: CH2
- c -

>
-

Formation :

in the
2
. By reaction of chloroform
alkali .
presence of a
strong

CH-C + RO - ROH +
U
C:
Uzc : U
>
-
: +
 .
2 By decomposition of diazo methane

or Getere in presence of UV
light .

WV
N
- -

= N >
HzC : + N2
Hzc =

( co
H(c
= c = 0
Hzc : +

order of carbenes
=>
Stability

Triplet >
Singlet
Carbenes
carbenes

⑨ O
Y - ⑧
Y C 3

j 8
 .
2 By Photolysis or Thermolysis
of Azides

S UV
R -
N = N = N - RN : +
N2
V W 00

Alkyl Azide Alkyl nitrere

O
O
R -
I -
NE = N er -
b - x + N2
&
Nitrene
Acyl Azide Acy1

3
. By Photolysis of Alkyl Isocyanates

R -

N
S
= c=0 # R-;: + co
ja

.
4
By decomposition of N-bromo
Amides

ea Ri
O

C z
R -
- N -
Br - : + HB
 Structure :

A
H-
G
N H

Ob
- -
u·

(Singlet] [Triplet)
>
- No
magnetism >
-
Magnetic

Stability -

Triplet > singlet

E- I
[Benzyne)