KOH aqueous heat under reflux SN

dihaloalkane
poly(alkene)
high pressure catalyst

diol

Br2, Cl2 room temp EAdd

alkane alkene
1 H2SO4 EAdd 2 H2O warm hydrolysis
conc. H2SO4 or conc. H3PO4 El, dehydration KOH aqueous heat under reflux NuSub

HBr, HCl room temp EAdd

Br2, Cl2 UV light Fr Sub

KOH alcoholic heat under reflux El

alcohol
NaBH4 Red Nu Add NaBH4 Red Nu Add Alcoholic KCN heat under reflux NuSub

haloalkane
Alcoholic NH3 heat under pressure NuSub LiAlH4 red haloalkane NuSub

If primary Na2Cr2O7/H+ heat and distill p.ox

If secondary Na2Cr2O7/H+ heat ox

nitrile
Caboxylic acid + H2SO4 heat esterification

1o amine

aldehyde

ketone
NaCN + H2SO4
Nu Add

2o amine 3o amine Quaternary salt

Acyl chloride room temp Nu add/elim

(If primary) Na2Cr2O7/H+ heat under reflux + excess oxidising agent Ox

hydroxynitrile
Alcohol + H2SO4 heat esterification

Esters and amides can be hydrolysed by NaOH and acids

secondary amide
1o amine room temp Nu add/elim

carboxylic acid

ester
Alcohol room temp Nu add/elim

H2O room temp Nu add/elim

Primary amide
NH3 room temp Nu add/elim

Acyl chloride/ acid anhydride

Copyright N Goalby Bancroft's School

Aromatic synthetic routes

NO2
conc nitric acid + conc sulphuric acid Electrophilic substitution acyl chloride in the presence of anhydrous aluminium chloride catalyst Electrophilic substitution

NH2
Sn and HCl reduction CH3Cl Nu sub

NH

CH3

CH3COCl Nucleophilic add-el

O C CH3
O
NaCN + H2SO4
Nu Add

NH
H

O C

CH3

C CN CH3

NaBH4 Red Nu Add

H O CH CH3

LiAlH4 reduction

OH C CH2 NH2 CH3

CH3CO2H + H2SO4 heat esterification

O H3C CH O C CH3

Functional group Alkene Aldehyde Aldehyde Carboxlic acid 1o 2o alcohol and aldehyde haloalkane Acyl chloride

Reagent Bromine water Fehlings solution Tollens Reagent Sodium carbonate Sodium dichromate and sulphuric acid Warm with silver nitrate Silver nitrate

Result Orange colour decolourises Blue solution to red precipitate Silver mirror formed Effervescence of CO2 evolved Orange to green colour change Slow formation of white precipitate Vigorous reactionsteamy fumes- rapid white precipitate

2
Copyright N Goalby Bancroft's School