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Summary Mechanisms of Organic Chemistry Reactions

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Summary of Mechanisms of Organic Chemistry Reactions

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B17CA A Guide to Substitution and Elimination

Summary

Haloalkane Notes


Methyl SN2 is the ONLY substitution reaction observed
CH3–X
Elimination is not possible!



Primary SN2 is the main reaction with moderate and strong nucleophiles e.g. OH–, EtO–,
RCH2–X CH3CO2–, CN–

E2 competes as a minor pathway where the nucleophile is basic e.g. OH–, EtO–

E2 becomes the major pathway with bulky alkoxides e.g. tert-butoxide Me3CO–

SN1 / E1 reactions do NOT occur



Secondary SN2 is the main reaction with good nucleophiles that are weak bases e.g.
R2CH–X CH3CO2–, CN–

E2 is the main reaction with stronger bases e.g. OH–, EtO–

SN1 / E1 reactions may occur with weak nucleophiles in polar protic solvents e.g.
water and alcohols



Tertiary SN2 reactions are never observed because of extreme crowding
R3C–X
E2 is the main reaction with strong bases e.g. OH–, EtO–

SN1 / E1 are the main reactions with weakly basic nucleophiles in polar protic
solvents e.g. water and alcohols




Foundations in Organic Chemistry • B17CA 19

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