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 Haloalkanes
Alkyl Group
Example
R-X Halogen
(F, Cl, Br, I)

sp3 hybridized
carbon
Nature of
C-X
Bond
 Nature of C-X Bond
ꞵ ꞵ-
C+ X Polar Covalent
Bond

“Due to electronegativity
difference”
 Order of Dipole Moment
Dipole Moment (μ) =qxd
CH3Cl > CH3F > CH3Br > CH3I
“Due to shorter C-F bond length”

μCH3Cl > μCH3F

 Methods of
Preparation of
Haloalkanes
 Preparation of Haloalkane
From Alcohols
HCl + ZnCl2
R-Cl + H2O
NaBr + H2SO4
R-Br + NaHSO4 + H2O
PCl5
R-OH R-Cl + POCl3 + HCl
Red P/X2
R-X
SOCl2
R-Cl + SO2 + HCl
PX3
3R-OH 3R-X + H3PO3 (X=Cl,Br)
 Preparation of Haloalkane
From Alkanes
Cl2/h𝜈 Cl2/h𝜈 Cl2/h𝜈 Cl2/h𝜈
CH4 CH3Cl CH2Cl2 CHCl3 CCl4
 Preparation of Haloalkane
From Alkenes

Example
CH3CH=CH2 + HCl CH3CHClCH3 + CH3CH2CH2Cl
 Preparation of Haloalkane
From Alkenes

∝
NBS CH2
R CH2 CH CH2 R CH CH

Allylic Carbon Br

N – Br (N – Bromo Succinimide)

O
 Preparation of Haloalkane
Finkelstein Reaction
Acetone, Δ
CH3X + NaI CH3I + NaX
X= Cl, Br
 Preparation of Haloalkane
Swarts Reaction

CH3-Br + AgF CH3F + AgBr

 Preparation of Haloalkane
Hunsdiecker Reaction
CCl4, Reflux
CH3CH2COOAg + Br2 CH3CH2-Br + CO2 + AgBr
 Chemical
Reactions of
Haloalkanes
 Chemical Reactions

Nucleophilic Elimination Reaction with

Substitution Reactions Metals
 Chemical Reactions
Nucleophilic Substitution Rxn.

SN2 Reaction SN1 Reaction

Substitution nucleophilic Substitution nucleophilic
Bimolecular Unimolecular

Rate = k[R-X] [Nu] Rate = k[R-X]

 SN2
Reaction
Chemical Reactions
SN2 Reaction
 Chemical Reactions
SN2 Reaction
CH3Br + NaOH CH3OH + NaBr
Mechanism

ꞵ- ꞵ-
Chemical Reactions
SN2 Reaction
 Chemical Reactions
SN2 Reaction
Reactivity order - Methyl > 1° > 2° > 3° Alkyl halide
 Chemical Reactions
SN2 is favoured by

Strong Good Leaving

Polar aprotic
Nucleophile group
solvent
● Aq KOH ● Acetone
● I- ● DMSO I- > Br- > Cl- > F-
● CN–
Important
SN2
Examples
 Important SN2 Examples
Reaction with KCN

KCN
CH3-CH2-Br CH3-CH2-CN + KBr
 Important SN2 Examples
Reaction with AgCN
AgCN
CH3-CH2-Br CH3-CH2-NC + AgBr
Important SN2 Examples
Reaction with KNO2
Important SN2 Examples
Reaction with AgNO2
Important SN2 Examples
Williamson Synthesis
 SN1
Reaction
Chemical Reactions
SN1 Reaction
 Chemical Reactions
SN1 Reaction

(CH3)3CBr + -OH (CH3)3COH + Br-

2-Bromo-2-methyl propane 2-Methylpropan-2-ol

Rate = k[(CH3)3CBr]
 Chemical Reactions
SN1 Reaction
Mechanism
Chemical Reactions
SN1 Reaction
Chemical Reactions
SN1 Reaction
 Chemical Reactions
SN1 Reaction
Reactivity order - 3° > 2° > 1° > Methyl halide

“Due to more stability of 3° carbocation”

 Chemical Reactions
SN1 is favoured by

Weak Good Leaving

Polar protic
Nucleophile group
solvent
● H 2O
● ROH ● Methanol I- > Br- > Cl- > F-
● H 2O ● Ethanol
Elimination
Reaction
Chemical Reactions
ꞵ -Elimination Reaction
 Chemical Reactions
ꞵ -Elimination Reaction
Example

Alc. KOH, Δ
Reaction
With
Metals
 Reaction with Metals
Reaction with Mg
Mg/dry ether
CH3-CH2-Br CH3-CH2-MgBr
 Reaction with Metals
Reaction with Na

Dry ether
CH3Br + 2Na + CH3Br C2H6 + 2NaBr
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