Lecture notes
Behaviour of Biomolecules lecture notes: Elimination Reactions
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- (BIOL1021)
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- University Of Southampton (UOS)
Behaviour of Biomolecules module Lecture notes: Elimination Reactions
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BIOL1021: Behaviour of BiomoleculesDr. Ramon Rios: rrt1f11@soton.ac.uk
Behaviour of Biomolecules
Lecture 2: Elimination Reactions
, Summary Lecture 1
Nucleophilic Substitution at Saturated Carbon
2. Consider if the leaving group departs, then the nucleophile arrives.
The nucleophile
S Na
H H Leaving
Group H + Cl
Cl Departs S
H
Nucleophile H H
Arrives
The electrophile Intermediate + Na
Carbocation
This is a two-step mechanism: Step 1: The leaving group departs (SLOW)
Step 2: The nucleophile arrives (FAST)
The rate of reaction depends only on [PhCH2Cl] and the rate is NOT increased by
increasing [nucleophile] so the step involving PhCH2Cl is rate determining = Step 1.
The rate determining step is unimolecular (electrophile only) so this mechanism is
called SN1.
, Nucleophilic Substitution at Saturated Carbon
3. Consider if the arrival of the nucleophile and the departure of the leaving
group occur simultaneously.
bonds partly
The nucleophile formed/broken
S Nucleophile
H H Arrives - H H -
AND S Cl
Cl Transition state
+
Electrophile
Na Departs
The electrophile
This is a one-step mechanism: S
The rate is dependent on both the + Cl + Na
[nucleophile] and the [electrophile].
The rate determining (only) step is bimolecular (electrophile and nucleophile) so
this mechanism is called SN2. Inversion of the configuration!!!!
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