SN1 SN2

Alkyl Halide 3°>2°>1° 1°>2°>3°

Leaving group

Nucleophile --- Strong Nu

Solvent PPS PAS

 NSR in alkyl halide
Generally,
SN1 reaction
SN2 reaction
Undergo both SN1 and SN2 reaction.

SN1 SN2
favoured by a poor nucleophile favoured by srong nucleophile
(H2O, ROH) & PPS (Anionic nucleophiles) & PAS

Benzyl halide and allyl halide show both SN1 and SN2 reaction.
 1. Reaction with H2O or CH3OH
If the solvent acts as nucleophile then the reaction is known as solvolysis.
If the solvent is water then is known as hydrolysis.
(Hydrolysis )
 Major Product ?

(1) (2) (3) (4)

2. Reaction with aq. KOH / aq. NaOH
 Major Product ?

(1) (2) (3) (4)

(1) (2) (3) (4)
(1) (2) (3) (4)
(2) WITH OR (ALKOXIDE ION) WILLIAMSON ETHER SYNTHESIS (SN2)
sodium ethoxide
Q: How to form alkoxide ion ?
Ans: Reaction of OH group with Na metal or base

alkoxide ion
 Phenetole
sodium phenoxide (ethoxybenzene)

sodium phenoxide anisole (methoxybenzene)

 Major Product ?

(1) (2)

(3) (4)
 Which set is preferred ?

(1) =

(2) =

HINT: Halide part should be smaller for williamson ether synthesis

due to greater SN2 reactivity
 Which set is preferred ?

(1) =

(2) =

HINT: Halide part should be smaller for williamson ether synthesis

due to greater SN2 reactivity
 Which set is preferred ?

(1) =

(2) =
Q. Which of the following ethers cannot be synthesized
using Williamson ether synthesis?

(1) (2)

(3) (4)

(5) (6)

Trick : Atleast one of R or R’ must be primary & sp3 hybridized.

4. Reaction of alkyl halide with NaNO2 / KNO2 and AgNO2

Ionic Covalent
Silver nitrite
Ambident nucleophile

(Major)

(Major)
5. Reaction of alkyl halide with NaCN / KCN and AgCN

Ionic Covalent

(Major) (alkane nitrile)

(Major) (alkane isonitrile)

Q: Butanenitrile may be prepared by heating ?

(1) Propyl alcohol with KCN

(2) Butyl alcohol with KCN

(3) Butyl chloride with KCN

(4) Propyl chloride with KCN

 5. HALOGEN EXCHANGE REACTION

FINKELSTEIN REACTION (Preparation of alkyl iodide)

NaI is soluble in dry acetone whereas NaCl and NaBr are insoluble.
NaCl and NaBr precipitate out in dry acetone which shifts the reaction in forward
direction according to Le-Chateliar’s Principle

SWARTS REACTION (Preparation of alkyl fluoride)

The synthesis of alkyl fluorides is best accomplished by heating an alkyl chloride/
bromide in the presence of a metallic fluoride such as AgF , Hg2F2 , CoF2 or SbF3
 Major Product ?

(1) (2) (3) (4)

Major Product ?

(1) (2) (3) (4)

6. Reaction of alkyl halide with dry Ag2O and moist Ag2O
7. Reaction of alkyl halide with NH3

Quaternary ammonium salt

This process is known as Hoffmann ammonolysis process

8. Reaction of alkyl halide with other nucleophiles-
(1) (2)

(3) (4)
 Major Product ?

(1) (2) (3) (4)

 Major Product ?

(1) (2) (3) (4)

NEET 2016

X and Y are respectively ?

(1) X= 1-Butyne and Y= 3-Hexyne

(2) X= 2-Butyne and Y= 3-Hexyne

(3) X= 2-Butyne and Y= 2-Hexyne

(4) X= 1-Butyne and Y= 2-Hexyne

NSR OF ALCOHOLS
 (1) REACTION WITH CONC. H-X

(SN1)

(SN1)

Generally, All alcohol react with HX through SN1 mechanism except CH3OH
and less bulky primary alcohol which react through SN2
IMPORTANT POINTS
1. Rate of reaction : H-I H-Br H-Cl H-F (for questions)
2. The reactivity order of alcohols towards H-X

Q: Compare reactivity of the following alcohols towards H-X?

1.

2.
 Major Product ?

(1) (2) (3) (4)

 Major Product ?

(1) (2) (3) (4)

 Major Product ?

(1) (2)

(3) (4) None

 Major Product ?

Neopentyl alcohol

(1) (2)

(3) (4)
 Major Product ?

(Ethylene glycol)

(1) (2) (3) (4)

(Ethylene glycol) (vicinal iodides are

unstable)
 Major Product ?

(1) (2) (3) (4)

(glycerol)

(2-iodopropane)
Brainstorming Questions

Major Product ?
SN 2

(1) (2)

(3) (4)
 HOME WORK on 02-01-2021

Module 3: chapter 4 (rxn mechanism ii )

Ex 1= Q 33 to 51, 53 to 55
Ex 2= Q 29, 31, 38, 41, 46, 51
Ex 3= 15 to 19

12th NCERT :
• Chemical properties of alkyl halide