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LDA
E2
Concen. HCl + Heat
Sn1
HCl
Addition (most sub) + epoxide opener
Concen. H2SO4 / H3PO4 + Heat
E1 alcohol eliminator
NaH + LG
Epoxide creator
A) NaH B) BrCH2CH3
Carbon chain addition to Oxygen
Excess NaNH2 + Heat
Double E2
A) NaNH2 B)…
Deprotonater
Br2
Addition (opp. stereochem.)
Br2, H2O
Addition (Br least sub., OH most sub.)
A) Hg(OAc)2, H2O B)NaBH4
Addition (OH to most sub carbon)
Grignard
Epoxide opener (least stable carbon), ketone breaker to add carbon chain
LiAlH4
Alcohol, Amine, Alkane creator
A) NaBH4 B) H+
Alcohol creator
mCPBA
Makes epoxides (from alkenes)
Mg, Li
Grignard creators from LG - R
A) BH3 B)HOO-
Adds OH to Alkenes on Least Sub carbon
A) O3 B) DMS
Adds oxygen to double bond ends
A) OsO4 / KMnO4 B)NaOH, H2O
Addition of 2 OH groups to alkene (same stereochem.)
CH2N2
Alkene to “carbon epoxide”
H+, H2O + heat / HgSO4, H2SO4, H2O
Alkyne to Ketone
A) Hb(Sia)2 B)HOO-
Alkyne to Aldehyde
Br2 + light
Br addition to most sub. carbon
Cl2 + Light
Non-regiospecific Cl addition
HBr, ROOR + Light
Addition (Br on least sub. of double)
H2Pd
Alkyne, Alkene to Alkane
H2, Lindlars
Alkyne to Z Alkene
Li, NH3 (l)
Alkyne to E Alkene
PositiveMoleculeCN, H2O
Sn2 (C - - -N)