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Organic Chemistry Reactions
H-X (excess)
markovnikov if terminal

H2O and acid or H3O+
markovnikov if terminal

Hg(OAc)2, H2O
NaBH4
internal

Hg(OAc)2, H2O
NaBH4
markovnikov; terminal

BH3, THF
H2O2, NaOH, H2O
syn; internal

BH3, THF
H2O2, NaOH, H2O
anti-markovnikov; syn; terminal

X2 (excess)
anti

H2, Pd/C
syn

Na, NH3
anti

H2, Lindlar’s catalyst
syn

NaNH2
Primary Alkyl Halide

strong base (KOH, NaNH2) excess
anti (elimination)

H-X excess
markovnikov

H2O and acid or H3O+
markovnikov

Hg(OAc)2, H2O
NaBH4
markovnikov

BH3, THF
H2O2, NaOH, H2O
anti-markovnikov; syn

HBr, ROOR
anti-markovnikov

X2
anti

X2, H2O
markovnikov (oxygen); anti

H2, Pd/C
syn

mCPBA
syn

mCPBA
H3O+
anti

OsO4, NMO
syn

O3
Zn, H3O+ or DMS

Diol formation
HIO4, H2O

CH2I2, Zn(Cu)
syn

Methyl - strong nucleophile/weak base
Sn2
Methyl - strong nucleophile/strong base
Sn2
Primary - strong nucleophile/weak base
Sn2
Primary - strong nucleophile/strong base
Sn2, minor E2
Primary - weak nucleophile/strong base
E2
Secondary - strong nucleophile/weak base
Sn2*/E2 at high temperature
Secondary - strong nucleophile/strong base
E2/minor Sn2
Secondary - weak nucleophile/strong base
E2
Tertiary - weak nucleophile/weak base
Sn1/E1 at high temperature
Tertiary - strong nucleophile/weak base
Sn1
Tertiary - strong nucleophile/strong base
E2
Tertiary - weak nucleophile/strong base
E2
Weak base/weak nucleophile
H2O, HO-R, HS-R
Weak base/strong nucleophile
SH-, SR-, CN-, I-, Br-, Cl-
Strong base/weak nucleophile
KOtBu, DBU, DBN, LDA, NaH
Strong base/strong nucleophile
OH-, NH2-, acetylide