Paaras Thakur

Organic Chemistry

SN1 and SN2

Reactions - 3
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Example In a nucleophilic substitution reaction:

Which one of the following undergoes complete inversion of configuration?

(a) C6H5CHC6H5Br (b) C6H5CH2Br
(c) C6H5CH2CH3Br (d) C6H5CCH3C6H5Br
(JEE Main Online 2014)
Example The order of reactivity of the following halides towards a SN1 reaction is

(a) II > III > I (b) III > II > I

(c) III > I > II (d) I > III > II
Example Predict the compound in each pair that will undergo solvolysis (in aqueous
ethanol) more rapidly.
Example Vinyl and aryl halides generally don't undergo SN1 or SN2 reactions.
Explain why ?
Nucleophilic Substitution
Ion pair effect in SN1 reaction
Example KI in acetone, undergoes SN2 reactions with each P, Q, R and S. The rates of
the reactions vary as

(a) P > Q > R > S

(b) S > P > R > Q
(c) P > R > Q > S
(d) R > P > S > Q (JEE
Advanced, 2013)
Example Draw perspective structures or Fischer projections products of the substitution
products of the following reactions.
Example Predict the products of the following SN2 reactions.

(1)

(2)

(3)

(4)
Example Predict the products of the following SN2 reactions.

(5)

(6)

(7)

(8)
Example The order of reactivities of the following alkyl halides for a S N2 reaction is
(a) RF > RCl > RBr > RI
(b) RF > RBr > RCl > RI
(c) RCl > RBr > RF > RI
(d) RI > RBr > RCl > RF (IIT 2007)
Example An SN2 reaction at an asymmetric carbon of a compound always gives
(a) An enantiomer of the substrate
(b) A product with opposite optical rotation
(c) A mixture of diastereomers
(d) A single stereoisomer (IIT 2007)
Example (a) Mixture of (i) and (ii)
(b) Mixture of (i) and (iii)
(c) Only (iii)
(d) Only (i)
Example
 Internal Nucleophilic Substitution - SNi

Case 1: Retention Of Configuration

 Internal Nucleophilic Substitution - SNi

Case 2: Inversion Of Configuration

 Elimination Reactions of Alkyl Halides

General Reaction
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