Chemistry - Reaction Pathways (All)

conc. HNO3, conc. H2SO4 catalyst, 50-60 C

nitration / electrophilic substitution

Sn / conc. HCl

reduction

Br2

Electrophilic Substitution

Br2 / AlBr3 or Fe or FeBr3

Bromination / Electrophilic Substitution

CH3Cl, AlCl3 catalyst, anhydrous

alkylation / electrophilic substitution

Cl2 / AlCl3 or Fe or FeCl3

chlorination / electrophilic substitution

CH3COCl, AlCl3 catalyst, anhydrous

acylation / electrophilic substitution

NaBH4

reduction

dilute HNO3

nitration / electrophilic substitution

Br2

bromination / electrophilic substitution

NaOH(aq)

H2 / Ni, 150 C

Electrophilic Addition / hydrogenation

Alkene → Alkane

Hydrogen halide, room temp

electrophilic addition

Alkene → Haloalkane

H2O (steam) / H3PO4

hydration

Alkene → Alcohol

Halogen, UV

free radical substitution

Alkane → Haloalkane

NaCN or KCN in ethanol

nucleophilic substitution

Haloalkane → Nitrile

NH3 in ethanol

nucleophilic substitution

Haloalkane → Amine

NaOH(aq), reflux

nucleophilic substitution

Haloalkane → Alcohol

K2Cr2O7 / H2SO4, distill

oxidation

Alcohol → Aldehyde

K2Cr2O7 / H2SO4, reflux

oxidation

Alcohol → Carboxylic Acid

Al2O3 or conc. H2SO4 or conc. H3PO4 / heat

elimination / dehydration

Alcohol → Alkene

Sodium Halide / H2SO4, heat under reflux

nucleophilic substitution

Alcohol → Haloalkane

Carboxylic acid/ conc. H2SO4 or Acid anhydride or Acyl chloride

Esterification

Alcohol → Ester

NaCN(aq) / H+(aq)

nucleophilic addition

Adlehyde / Ketone → Hydroxynitrile

NaBH4 / H2O

Reduction

Aldehyde / Ketone → Alcohol

hot aqueous alkali

alkaline hydrolysis

Ester → Carboxylate salt

Alcohol / conc. H2SO4

esterification

Carboxylic acid → Ester

SOCl2

chlorination

Carboxylic acid → Acyl chloride

H2O

hydrolysis

Acyl chloride → Carboxylic acid

NH3

nucleophilic addition elimination

Acyl chloride → Primary amide

Primary amine

nucleophilic addition elimination

Acyl chloride → Secondary amide

Alcohol

Acyl chloride → Ester

H2 / Ni

Nitrile → Amine

dilute hot aqueous acid

acid hydrolysis

Ester → Carboxylic acid

H2O, HCl, heat

hydrolysis

Nitrile → Carboxylic acid

K2Cr2O7 / H2SO4, reflux

oxidation

Aldehyde → Carboxylic Acid

K2Cr2O7 / H2SO4, reflux

oxidation

Alcohol → Ketone

H2 / Ni

Hydroxynitrile → Amine