Mechanism Determination Flashcards
strong vs weak nuc/base, determine whats SN1 SN2 E1 and E2
Strong nuc, weak base 1*
SN2
Strong nuc, weak base 2*
SN2
Strong nuc, weak base 3*
SN1
Weak nuc, strong base 1*
E2
Weak nuc, strong base 2*
E2
Weak nuc, strong base 3*
E2
Strong nuc, strong base 1*
E2 (minor) + SN2 (major)
Strong nuc, strong base 2*
E2 (major) + SN2 (minor)
Strong nuc, strong base 3*
E2
Weak nuc, weak base 1*
SN2 + E2 (impractical?)
Weak nuc, weak base 2*
All reactions (impractical)
Weak nuc, weak base 3*
SN1 + E1
NaOH
strong nuc, strong base
NaOMe
strong nuc, strong base
NaOEt
strong base, strong nuc
H2SO4 + heat
E1
H2O
weak nuc, weak base
NaSH
strong nuc, weak base
tBuOK - Potassium Tertbutoxide
(draw out)
E2 ONLY - sterically hindered so hofmann is major
NaSMe
strong nuc, weak base
LOA
E2
MeOH
weak nuc, weak base
How to determine if a weak or strong nuc:
If negative charge, then strong.
If no negative charge, then weak.
How to determine a weak or strong base:
strong: negatively charged oxygens, less electronegative atoms
weak: neutral, high electronegative atoms (halides - Cl, Br, I), resonance stabilized
LDA - Lithium Diisopropyl Amine
(draw out)
Elimination, E2
weak nuc, strong base
NaH
weak nuc, strong base
NaCN
strong nuc, weak base
MeOH
weak nuc, weak base
If weak nuc, weak base, and bad LG then
NR
If neopentyl
NR
