Helpful chart for SN1, SN2, E1 and E2 Organic Chemistry Reactions

Factors                        SN1                                SN2                         E1                             E2
nucleophile:               any(often weak)     ;    good, strong
base:                        any (often weak)    ;   must have strong
substrate                    3>2                      ;    methyl > 1 > 2          ;    3 > 2                ;       3 > 2> 1
leaving group:       good; conjugate base of stong acids --------------------------------------->
solvent:                     polar protic            ;     depends on               ;  good                   ;    wide variety
                              (maybe aprotic)            what you want               ionizing
kinetics:                1st order k[R-X]          ;2nd order k[R-X] [Nu:]   ;1st order k [R-X]   ; 2nd order k[R-X] [B:]
stereochemistry:         racemic                 ; inversion                       ;Zaitsev                 ;     Zaitsev
rearrangement:         common (2 --> 3)    ;impossible                     ;common (2 --->3) ; impossible
orientation:                                                                                    ; none                    ;  anti (180)


I’m confused. This table is essentially of use only to people who understand exactly what the table is meant to help elucidate. Some of it is not correct (or incomplete) for example:
The E2 reaction does not always end up with a Zaitzev product...that is the entire point of the Hoffman (anti-Zaitzev) regiochemical concept. If fluorine is the LG, if KOtBu is the base, if the Cope elimination is used...etc. Also, the SN1 reaction does not involve a base at all, let alone “any” base...
It’s an okay but very cursory and confusing attempt. 


Joshua J.

Math, Science, Reading, and Writing!

100+ hours
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