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Mechanisms Cheat Sheet (DRAFT) by

This is a draft cheat sheet. It is a work in progress and is not finished yet.


1. Proton Transfer
2. Carboc­ation Formation
3. Ion Attacks Carboc­ation
Favors 3rd and 2nd degree carboc­ations
Step 2 is RDS


Single Step:
- Cleavage of bond between C and leaving group
- Formation of bond between C and nucleo­phile
Favors methyl and 1st degree carboc­ations
Config­uration is inverted


1. Proton­ation of alcohol
2. Dissoc­iation to carboc­ation and water
3. Deprot­onation of cation
Favors 3rd degree carboc­ation
Often requires shifts
Dehydr­ation of OH


Single Step:
- Strong base takes proton
- Loss of halide
Can be used by any degree of alcohol w/ strong base
Favors third degree