Organic synthesis equations

Alkene to alkane

H2/Ni catalyst 150’C 5 atm

Addition

alkene to haloalkane

Hydrogen halide room temp

Electrophillic addition

alkene to alcohol

H2O (steam)/H3PO4

alcohol to alkene

H3PO4 or H2SO4, heat

Electrophilic addition (dehydration)

alkane to haloalkane

Halogen, UV light

alcohol to ester

Carboxylic acid and conc H2SO4 reflux OR acid anhydride (eg with Phenol)

alcohol to haloalkane

Potassium halide/H2SO4 reflux

haloalkane to alcohol

NaOH(aq) and reflux

primary alcohol to aldehyde

K2Cr2O7/H2SO4 distil

partial oxidation

aldehyde to primary alcohol

NaBH4

Reduction

secondary alcohol to ketone

K2CrO7/H2SO4 reflux

Oxidation

aldehyde to carboxylic acid

K2CrO7/H2SO4 reflux

Oxidation

carbox to acyl chloride

SOCl2

DATA SHEET

acylchloride to ester

alcohols/phenols room temperature

carbox to ester

alcohol/conc H2SO4 reflux

ester to carbox

diluted acid and heat

ester to carboxylate

OH- and heat

acyl chloride to primary amide

conc NH3 room temperature

acyl chloride to secondary amide

Primary amine

ACYLATION

aldehyde to hydroxynitrile

NaCN/H+

hydroxynitrile to amine

H2/Ni catalyst

Ketone to hydroxynitrile

NaCN/H+

hydroxynitrile to carboxylic acid

H2O/HCl and heat

nitrile to carboxylic acid

conc H2SO4/HCl and heat

Hydrolysis

haloalkane to nitrile

KCN in ethanol solution

haloalkane to amine

NH3/ethanol reflux

nucleophilic substitution

nitrile to amine

H2/Ni catalyst

Benzene to Bromobenzene

Br2 FeBr3 (Or just Fe) Room temp

Substitution

Benzene to chlorobenzene

Cl2 AlCl3 Catalyst warn

Chlorination

Benzene to Benzene sulfonic acid

Fuming H2SO4 40’C

Sulfonation

Benzene to alkyl benzene thing (C6H5R)

RCl AlCl3 catalyst Reflux

Alkylation

Benzene to aromatic ketone (eg C6H5COR)

ROCl AlCl3 catalyst Reflux

acylation

Benzene to nitrobenzene

H2SO4/HNO3 55’C

Nitration

Nitrobenzene to Aminobenzene

DATASHEET

Aminobenzene to diazonium ion

HNO2/HCl less than 5’C

Diazonium ion to azo compound

Phenol/NaOH less than 5‘C

Phenol to Sodium phenoxide

NaOH 20’C

Phenol to Ester (eg phenyl ethanoate)

CH3COCl 20’C