synthesis map

alkane → haloalkane

free radical substitution
UV light
X2

alkene → alkane

electrophilic addition
H2
nickel catalyst

alkene → haloalkane

Hx
X2

haloalkane → nitrile

NaCN/ethanol

haloalkane → amine

excess NH3/ethanol

haloalkane → alcohol

NaOH(aq)
nucleophilic substitution

alkene → alcohol

H2O(g), H3PO4/H+

alcoho → alkene

H2sO4 or H3PO4, heat

alcoho → haloalkane

NaX
H2SO4

secondary alcohol → ketone

H+/Cr2O72-, reflux

primary alcohol → aldehyde

H+/Cr2O72-, distillation

aldehyde → primary alcohol

NaBH4(aq), nucleophilic addition

primary alcohol → carboxylic acid

H+/Cr2O72-

aldehyde → carboxylic acid

reflux, Cr2O72-

ketone → secondary alcohol

NaBH4(aq), nucleophilic substitution

aldehyde → hydroxynitrile

NaCn(aq)/H+, nucleophilic addition

ketone → hydroxynitrile

NaCN(aq)/H+

hydroxynitrile → amine

H2
Ni

nitrile → amine

H2, Ni

nitrile → carboxylic acid

HCl/H2O, heat

alcohol → ester

carboxylic acid, concentrated H2SO4, heat

carboxylic acid → ester

alcohol, H2SO4, heat

ester → carboxylic acid

H+, heat

ester → carboxylate

OH-

acyl chloride → ester

alcohol

acyl chloride → carboxylic acid

H2O

carboxylic acid → acyl chloride

SOCL2

acyl chloride → primary amide

NH3

acyl chloride → secondary amide

primary amide