Alkane to Alkyl Halide
X?, light, heat
Alkyl Halide to Alcohol
OH?
Alkyl Halide to Ether
RO?
Alkyl Halide to Ester
RCOO?
Alkyl Halide to Nitrile
NaCN
Alkyl Halide to Alkyne
RC ? C?
Alkyl Halide to Alkane
1. LiAlH? 2. H?O
Alkyl Halide to Grignard
Mg, diethyl ether
Alkyl Halide to Amine
NH?
Alkyl Halide to Thiol
HS?
Alkyl Halide to Thioether
RS?
Alkyl Halide to Alkene
OH?
Alcohol to Alkyl Chloride
SOCl?, pyridine
Alcohol to Alkyl Bromide
HBr, PBr?
Alcohol to Alkyl Iodide
HI
Alcohol to Tosylate
TsCl, pyridine
Halohydrin to Epoxide
OH?
Alcohol to Alkene
H?SO?
Alcohol to Alkene
POCl?, pyridine
Alcohol to Aldehyde
PCC
Alcohol to Carboxylic Acid
CrO3, H?SO?, H?O
Alcohol to Ketone
PCC or CrO?
Alkene to Vicinal Diol
KMnO?, H?O, OH?
Alkene to Epoxide and Carboxylic Acid
RCO?H
Alkene to Vicinal Diol
1. RCO?H 2. H?O
Alkene to Alkane
H?, Pd, Pt, Ni
Alkene to Alkyl Halide
HX (and H?O? for Anti-Markovnikov)
Alkene to Alcohol (Anti-Markovnikov)
1. BH? 2. H?O?, OH?
Alkene to Alcohol (Markovnikov)
H?SO?
Alkene to Vicinal Dihalide
X?
Alkene to Halohydrin
X?, H?O
Ether to Alkyl Halides
HX
Epoxide to Alcohol
1. LiAlH? 2. H?O
Epoxide to Vicinal Diol
OH?, H?O+
Epoxide to Alcohol Thiol
HSH
Epoxide to Alcohol Thioether
1. RS? 2. H?O
Alkyne to Geminal Dihalide
2 HX
Alkyne to Tetrahalide
2 X?
Alkyne to Carboxylic Acids
1. O? 2. H?O
Alkyne to Carboxylic Acid and Carbon Dioxide
1. O? 2. H?O
Alkyne to Ketone
1. H?O 2. H?SO?, HgSO?
Alkyne to Acetylide
NaNH?, NaH
Acetylide to Alkyne
RX
Alkyne to Alkane (trans)
2 H?, PdC
Alkyne to Alkene (cis)
H?, Lindlar
Alkyne to Alkene
Na, NH?