Reaction

Mechanisms
LECTURE 13 Benzyne &
Ei Mechanism

NaNH2

solvent
NH3(I)
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 Reaction
Mechanisms
LECTURE 13 Benzyne &
Ei Mechanism

NaNH2

solvent
NH3(I)
Broad 3 Categories of Reactions and Mechanisms

ADDITION

Addition reaction occurs when two or more reactants combine to

form a product without the loss of any atoms present in the
reactants.

SUBSTITUTION
A chemical reaction during which one functional group in a
chemical compound is replaced by another functional group.

ELIMINATION

An elimination reaction is a type of organic reaction in which two

substituents are removed from a molecule.
 Type of nucleophilic substitution reaction:

Type of nucleophilic substitution reaction:

● SN1
● SN2
● SNi
● SN2Ar
● SN2Th
 Type of Elimination Reactions

There are three types of elimination reactions

(I) E1
(II) E2
(III) E1cB
 Benzyne Mechanism

Two mechanisms have been proposed for nucleophilic aromatic substitution,

- SN2Ar
- Benzyne mechanism
Benzyne Mechanism
 Benzyne Mechanism

sp2 orbitals involved in the triple bond are at 90o to the p orbitals of the aromatic pi system

Poor overlap leads to a very weak triple bond, easily broken by a nucleophile
Benzyne Mechanism
Benzyne Mechanism

NaNH2
solvent
NH3(I)
 Nucleophilic Substitution

Mechanism

Step 1
 Nucleophilic Substitution

Mechanism

Step 2
 Nucleophilic Substitution

Mechanism

Step 3
Nucleophilic Substitution

Na+ -NH2

NH3, -33oC
Example Propose mechanisms and show the expected products of the following
reactions.

A. 2,4-dinitrochlorobenzene + sodium methoxide (NaOCH3)

Example Propose mechanisms and show the expected products of the following
reactions.

2,4-dimethylchlorobenzene + sodium hydroxide, 350 °C

Example Propose mechanisms and show the expected products of the following
reactions.

p-nitrobromobenzene + methylamine (CH3— NH2)

Example
Nucleophilic Substitution

ortho- meta- para-

Never formed
 Nucleophilic Substitution

CH3 doesn’t have effect on nucleophilic attack but electron withdrawing groups (-I) like CF3 and
OCH3 affect the position of nucleophile
 Ei Elimination Reaction Mechanism

● Ei mechanism (Elimination Internal/Intramolecular) Also known as a thermal syn

elimination or a pericyclic syn elimination

● Two vicinal substituents on an alkane framework leave simultaneously via a cyclic

transition state to form an alkene in a syn elimination.
 Pyrolytic Syn Elimination Ei (Elimination Intramolecular)

● This type of elimination is unique because it is thermally activated and does not require
additional reagents. This reaction mechanism is often found in pyrolysis reactions.

● A number of organic compounds such as an amine oxide, ester or xanthate undergo pyrolytic
elimination of HX (in the absence of any reagent), either in an inert solvent or, in some cases,
in the gas phase.
 Pyrolytic Syn Elimination Ei (Elimination Intramolecular)

● In general these eliminations follow the rate law: Rate = K [substance]

 Ei Elimination Reaction Mechanism - Cope Elimination

When a tertiary amine oxide is heated at approximately 100oC, elimination reaction takes place as
follows:
Example
Example
Cope Elimination Regioselectivity
Cope Elimination Regioselectivity
 Ei Elimination Reaction Mechanism - Ester Pyrolysis

● When subjected to temperatures above 400 °C, esters containing β-hydrogens can eliminate
a carboxylic acid through a 6-membered transition state, resulting in an alkene.
Example
Example
Example
Ei Elimination Reaction Mechanism - Xanthate Ester Pyrolysis
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