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Nucleophilic Substitution and Elimination

1. The document discusses several types of organic reactions including nucleophilic substitution, elimination, addition, and rearrangement. 2. Nucleophilic substitution occurs when an electron-rich species provides an electron pair for bonding with the compound being transformed. Elimination reactions involve the removal of atoms or groups to form multiple bonds, such as dehydration reactions. 3. Addition reactions involve the breaking of pi bonds and formation of new sigma bonds, such as reactions involving electrophiles and unsaturated compounds. Rearrangement reactions involve the migration of atoms or groups within a molecule to form new bonds.

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Carl Ian Samonte
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0% found this document useful (0 votes)
10 views5 pages

Nucleophilic Substitution and Elimination

1. The document discusses several types of organic reactions including nucleophilic substitution, elimination, addition, and rearrangement. 2. Nucleophilic substitution occurs when an electron-rich species provides an electron pair for bonding with the compound being transformed. Elimination reactions involve the removal of atoms or groups to form multiple bonds, such as dehydration reactions. 3. Addition reactions involve the breaking of pi bonds and formation of new sigma bonds, such as reactions involving electrophiles and unsaturated compounds. Rearrangement reactions involve the migration of atoms or groups within a molecule to form new bonds.

Uploaded by

Carl Ian Samonte
Copyright
© All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd

Organic Reactions

SUBSTITUTION(SET 1)
Nucleophiliv It

018_K =Co-

+
H

* xo DH

H
o I CH
is
H
Reactant
PRODUCT

Nucleophilic Substitution

-
.--c]
post
a.... When electron-rich species
as in (nucleolphile) provides an electron pair
for bonding with the compound being
transformed, it is called nucleophilic ,
substitution

SET 2
I4
R-01 R-CI
Reactant Product

Electrophilic

R-Ol
At
DR-8A2 R8 Cls R-Cl
ELIMINATION (SET 1)

letis-1+

C13C
(CH3), 2016 + HC (CH3), (C1
= 6 1z0
.0:+
.e
:

DEAYDRATION
Reactant Product

It
+-butyl alcohol

EIMINATION


(213)32
(213) C"+ ici.
- (CH)s( : - H (C13), C"+H20
It dehydration method, there is the elimination of a
water molecule mostly from compounds such as
alcohol. Sometimes, this method is also called a
Beta elimination reaction where the leaving group
and H are placed at neighbouring carbon atoms.

SET 2

its elect als as (see


CHGC=
Product

C13
3 CI
8
↑ OH
I CH-C16
=

C1322 -

cits CACH-C-C

d
0 Itz
d
*
Fretrophilic
Electrophilic
Intermediate
ADDITION (SET1)
1 1 14 It
c- 16 1,2-dibromoethane
-
=
Br
+
-
Br H - - -

I
-A
1 Reactant Product Br Br

I ③

is--gr

17
14
Y= Br r= - 1 -

c -

2
-

ELECTROPHILIC
BrElectrophilic ir ir

ADDITION
SET 2 An electrophilic addition reaction can be described as an addition
reaction in which a reactant with multiple bonds as in a double or

chloride
triple bond undergoes its π bond broken and two new σ bonds are
Br

Cl6yCH
CH formed.
C3CH:CH2
tert-butyl
-

Reactant Product

216, CI*-
Intermediate
CH2
CH3CH= CH3
electrophilic
2163
-

CH -

CH3 Br*D CH3 -CH -


213
Electrophiliv Br
REARRANGEMENT
Br OA
Product

+ HBr
Reactant

Electrophilic
I ⑪
A

1620:
)
Nucleophilic Of

BrO
⑪ - D HBr

BECkmann
Rearrangement
Beckmann rearrangement , an oxime is
converted to an amide . An oxime is

SET
easily obtained by treatment of

2 aldehyde or ketone with hydroxylamine.


The OH group of ketoximes can become
a leaving group. The Beckmann
rearrangement of cyclic oximes results

Hy
in lactams.

CH3

CHz -
- -

Be I/120p CH -

C -clb2 -Clb3
Reactant dis Product

I C13 Electrophilic CH3 C13


↑ b- cs-c-ce
p
Cit3 ⑪ 2

CH
DCHge
-

-
Be -

CH methyl ⑪
-

d
-

Shift
die Electrophilic
REFERENCES

Stephen Gibbings. (2018, January 10). Organic Lesson 8 Substitution, Addition, and Elimination Reactions [Video]. YouTube.
[Link]

Bhuyan, S. (2022, July 5). Elimination Reaction: Definition, Examples, Mechanism, and Applications. Chemistry Learner. [Link]
[Link]

D. (2021, April 20). Write mechanism of the following reaction: CH3Cl+OH^- rarrCH3OH+Cl^- [Video]. Doubtnut. [Link]
answer-chemistry/write-mechanism-of-the-following-reaction-ch3cl-oh-rarrch3oh-cl--643852485

A. (2022, July 18). Elimination Reaction - E1 & E2 Reaction Mechanisms. BYJUS. [Link]
#:~:text=Normally%2C%20elimination%20reactions%20are%20distinguished,Dehydrohalogenation

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