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Substitution Reaction: Organic Chemistry Notes by Abdul Wasay

The document discusses substitution reactions, which involve replacing one atom or group with another. It describes three main types: nucleophilic, free radical, and electrophilic substitution reactions. Nucleophilic substitution reactions proceed by either an SN1 or SN2 mechanism. The SN1 is a unimolecular reaction that takes place in tertiary substrates, proceeding through a carbocation intermediate. The SN2 is a bimolecular reaction that occurs simultaneously, with nucleophilic attack from the opposite side in primary substrates. Factors like solvent, nucleophile strength, and substrate structure determine whether the SN1 or SN2 pathway is favored.

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146 views6 pages

Substitution Reaction: Organic Chemistry Notes by Abdul Wasay

The document discusses substitution reactions, which involve replacing one atom or group with another. It describes three main types: nucleophilic, free radical, and electrophilic substitution reactions. Nucleophilic substitution reactions proceed by either an SN1 or SN2 mechanism. The SN1 is a unimolecular reaction that takes place in tertiary substrates, proceeding through a carbocation intermediate. The SN2 is a bimolecular reaction that occurs simultaneously, with nucleophilic attack from the opposite side in primary substrates. Factors like solvent, nucleophile strength, and substrate structure determine whether the SN1 or SN2 pathway is favored.

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Organic Chemistry notes by Abdul Wasay

 Substitution Reaction
The substitution reaction is defined as a reaction in which the functional group of
one chemical compound is substituted by another group or it is a reaction which
involves the replacement of one atom or a molecule of a compound with
another atom or molecule.

Types of Substitution Reaction


1. Nucleophilic Substitution Reaction (with Sn1 & Sn2 Mechanism)
 Nucleophilic aliphatic substitution reaction
 Nucleophilic aromatic Substitution reaction
2. Free Radical Substitution Reaction
3. Electrophilic Substitution Reaction
 Electrophilic aliphatic substitution reaction
 Electrophilic aromatic substitution reaction

1. Nucleophilic Substitution Reaction:


A Nucleophilic substitution reaction in organic chemistry is a type of reaction
where a nucleophile gets attached to the positive charged atoms or molecules of the
other substance.

 The reaction in which Halogen(X) of A lkly halide is substituted by a


nucleophile then it is called nucleophilic substitution reaction.
 They behave like saturated compounds, that’s why they undergoes
substitution reaction.
1) Substrate: The molecule on which substitution takes place known as
“substrate”.
2) Nucleophile: A nucleophile is an electron rich species that will react with
an electron poor species.
i) Very good nucleophiles: HS, I, RS
ii) Good nucleophiles: BR, HO, RO, CN, N3
iii) Fair nucleophiles: NH3, Cl, F, RCO2
iv) Weak nucleophiles: H2O, ROH
v) Very weak nucleophiles: RCO2H
 Weak nucleophiles are neutral and don’t bear a charge. Some
examples are CH3OH, H2O and CH3SH.
3) Leaving Group
1. Good Leaving Group (Weaker bases are better leaving groups)
Eg; TsO, NH3, I, H2O, Br, Cl, etc.
2. Bad Leaving Group (The conjugate base of weak are poor leaving groups).
Eg; F, OH, NH2, Alkane, H etc.

4) Solvents
1. Polar protic solvents (all those solvents which includes H2 bonding).
Eg; H2O, CH3OH, Formamide, N-methyl formamide, CH2CH3OH, Acetic acid,
n-propanol, t-butanol.

2. Polar aprotic solvents (those solvents which do not includes H2 bonding)


Eg; Acetone, Ethanenitrile(Acetonnitrile), N,N Dimethly formamide(DMF), Dimethly
Sulfoxide(DMSO), Nitro-Methane, Pentane, Hexane, Benzene, Toulene, Chloro-Methane, Diethlyether.
Mechanism of Nucleophilic substitution reaction:
Two mechanisms of nucleophilic substitution reaction are discussed here. SN1
reaction and the SN2 reaction, where S represents chemical
substitution, N represents nucleophilic, and the number stands for the kinetic
order of a reaction.

SN2 Reaction:

In this reaction, the elimination of the leaving group and the addition of
the nucleophile occur simultaneously. SN2 takes place where the central
carbon atom has easy access to the nucleophile.

Eee

Name of Mechanism Bi-molecular substitution reaction

Molecularity/Order: 2 (RX) (NU)


(number of molecules taking part in slow step/rate
determining step)

Which R-X will undergoes this


mechanism? 1º RX(Primary Alkyl Halides)

Steps One Step(slow)

Transition State:
(A state in which bonds are half broken) Yes

NU attacks from which side? Left

Rate Expression: dt/dx ∝ [RX][NU]


Example: Reaction of Ethyl Chloride with aqueous KOH

Another Example:
SN1 Reaction:
The SN1 reaction is a type of nucleophilic substitution reaction in which an electron-
rich nucleophile displaces the halogen atom bonded to the central carbon of an alkyl
halide molecule. The halide ion that is displaced from the carbon atom is called the
leaving group. SN1 reaction takes place at the site of a saturated carbon atom.
Name of Mechanism Unimolecular substitution reaction

Molecularity/Order: 1(RX)
(number of molecules taking part in slow step/rate
determining step)

Which R-X will undergoes this 3º RX (Tertiary)


mechanism?

Steps Two steps

Transition State:
(A state in which bonds are half broken) No

NU attacks from which side? Right

Rate Expression: dx/dt ∝ [RX]

Example: Reaction of Tertiary Butyl Chloride with aqueous KOH


Another Example:

Strong nucleophile Sn2


Weak nucleophile Sn1
Polar protic solventSn1 e.g H2O, CH3OH
Polar aprotic solventsSn2 e.g Acetone, HCl
Weak bases favors Sn1
Strong bases favors Sn2
The Trend of Substrate reactivity for Sn1 & Sn2
Sn1: 3º>2º>1º>methyl(CH3)
Sn2: methyl>1º>2º >3º

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