Reaction Summary
Nucleophilic substitution: alkyl-leaving group -> alkyl-nucleophile
Nucleophile LG Nu Aprotic polar solvent Concerted reaction (Sy2)
Nucleophile - Protic solvent
Via carbocation intermediate (Syl)
Elimination: alkyl-leaving group -> alkene
Strong base G heat
H2SO4 heat
Concerted reaction (E2)
Via carbocation intermediate (E1)
Halogen addition: alkene -> vicinal dihaloalkane or halohydrin HO Br Anti addition Br2 Br2 (cyclic bromonium H2O CH2Cl2 ion) Br Br
ROH addition: alkene -> alcohol or ether OH H,SO4 H2SO4
R.
Markovnikov addition (no stereochem constraints)
H2O ROH Via carbocation intermediate
Oxymercuration/reduction: alkene -> alcohol or ether OH 1.Hg(OAc)2/HO 1.Hg(OAc)2/ROH 2.NaBH4 2.NaBH4
Markovnikov addition (Anti addition)
Hydroboration/oxidation: alkene -> alcohol
Anti-Markovnikov addition (Syn addition)
1.BH3
OH
2.NaOH/H2O2
Ozonolysis: alkene - > carboxylic acids or aldehydes OH HO 1.03 1.03
2.H2O2
2.(CH3)2S
Tosylate synthesis: alcohol -> tosylate Tosyl chloride Q (TsCl) C1 CH3 OH 0
R-OTs
CH3
Pyridine
Alkyl halide synthesis: alcohol -> alkyl halide
PBr3
OH
SOCl2
Pyridine
Alcohol oxidation: alcohol -> aldehyde
(PCC) CrO3
OH
Pyridine
Alcohol oxidation: alcohol -> carboxylic acid or ketone
OH
K,Cr2O7
HO
K,Cr2O7
OH
Glycol oxidation: glycol -> aldehyde and/or ketone
HO
OH
H:IO6
Nucleophilic substitution: alkyl-leaving group > alcohol
0 CH3 Aprotic polar solvent
NaOH/H2O
For secondary substrates
CH
OH
Concerted reaction (SN2)
Hydrogenation: alkene -> alkane
H2
Pd/C
Hydrogenation: alkyne -> alkane
H2
Pd/C
Hydrogenation: alkyne -> alkene
trans
Na
H2
NH3
Lindlar
Hydrogenation: aromatic -> aromatic or to alkane
H2
H2
Pd/C
Pt, high pressure
Glycol synthesis: alkene -> glycol OsO4
HC
H
H2O/t-butyl alcohol pyridine/TMAO
Syn addition
Epoxide synthesis: alkene -> epoxide
m-chloro- peroxy- C benzoic acid (MCPBA)
OH
Syn addition
Epoxide synthesis: halohydrin -> epoxide
Br
NaOH (1 equiv)
Sy2 attack by hydroxyl on carbon with Br
HO