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SubstitutñonlENminatjon Decision Map

Methyl Halide (~ J S~2

Primary Haloalkane I 1=~ [~uOi~ =~ ~E2l

0 ~HSN2I

~YD’=~I5N’__11*

* Note: With Very WeakBases, SN2 can competehere, but for the purposes ofthis class, assume SN1 / Elpredominate

** Note: If tHuOK is the verystrong base, an appreciableamount of a non-Zaitsevproduct can be formedbecause the bulky tBuOK willtend to react with the mostaccessible H atom.

Secondary

or

aloalkane =~ L~en’ Weak Base1] rz~>

8AllyIic/Benzylic Hal ‘des [yery Strong asel]

8~~JSN21

Tertiary Haloalkane ] cz~ [yery Weak ase cz>

11 ___

ii For SN2 Remember Chiral Center InVERSIONFor E2 Remember anti- riplanar and ZaitsevFor SN1 Remember Chiral Center ScramblingFor El Remember Zaitsev

Table ofNucleophiles

Strong Nucleophiles -

Br,I ;R-s,H-s~,NEc,N,

~ R-C~C, ~it-o’, H-& Strong Bases

Medium NucleophilesR-COj , R S-H, R2S,14H3, RNH2, R2NH, NR3

Thrt-Butoxide (tBuO) Is a strong base, butis not a nucleophile due to non-bonded

interaction strain.

R-CO2H, R-O-H, H20 Very Weak Bases

Special Case