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Behaviour of Biomolecules lecture notes: Elimination Reactions

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Behaviour of Biomolecules module Lecture notes: Elimination Reactions

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  • November 7, 2023
  • 23
  • 2023/2024
  • Class notes
  • Ramon rios
  • Elimination reactions
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BIOL1021: Behaviour of Biomolecules
Dr. 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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