Summary Synthetic Routes Cheat Sheet

electrophilic addition alkane b s tit ution nitrile
hydrogenation
free radical halogen l e o p h ilic su
H2 /Ni catalyst nuc - / ethanol
substitution UV CN H2
Ni catalyst
hydrogen halide
alkene electrophilic addition
haloalkane reduction
nucleophilic sodium halide

hydration
substitution
NaOH (aq)
H2 SO4
nucleophilic substitution
amine
H 2 O (steam) / H 3 PO4 catalyst K 2 Cr2 O 7 / H 2 SO4 reflux
alcohol ketone
elimination / dehydration NaBH4 reduction reduction
H 3 PO4 or H 2 SO4 catalyst / heat 1° 2° H2 /
K 2 Cr2 O 7 / H 2 SO4
NaBH4 Ni catalyst
distillation
reduction oxidation
K 2 Cr2 O 7 / H 2 SO4 reflux NaCN (aq) / H+ (aq) nucleophilic addition
oxidation aldehyde hydroxynitrile
K 2 Cr2 O 7 / H 2 SO4
reflux
oxidation
hydrolysis H 2 O /HCl heat
ester carboxylic acid
OH -
alkaline H2 O SOCl2
nucleophilic addition
NH3 1° amine
heat hydrolysis hydrolysis chlorination
primary amine
carboxylate acyl chloride nucleophilic addition
2° amine