ORGANIC FUNCTIONAL GROUP INTERCONVERSIONS

H H R1 O
Cracking (variety of products) R2 O2, Ag cat., 250-300˚C, 10-20 atm (ethene only); other alkenes: RCO3H in CH2Cl2
R1 C C R2 ALKANE C C ALKENE R1 C C R2 EPOXIDE
R3 R4 R3 R4
H2, Ni cat., 150˚C, 5 atm
H H
Polymerisation
ADDITION POLYMER
Hydrogen halide & UV light

Steam, 300˚C, 60 atm, conc. H3PO 4 cat.

Conc. H2SO 4

Al2O3, 300˚C, or conc. H2SO 4, reflux

Hydrogen halide (aq), room temperature

Hot, conc. KOH, alcoholic solution

O O
H2SO 4, heat (1˚ alcohols only) O
R1 R2 ETHER R1
C
O
C
R2
ACID ANHYDRIDE
H H
R1 C C R2 ALKYL HYDROGENSULFATE

H OSO3H

H2O, warm
R X HALOALKANE
O
1˚ only: Cr2O72-, H+, distil Cr2O72-, H+, reflux

H2O, reflux
P2O5, distil
NaOH (aq), reflux
R OH ALCOHOL C ALDEHYDE
KCN, ethanolic solution, reflux
NaBH4 (aq, heat) or LiAlH4 (ether)
R H
O
Conc. NH3, heat in sealed tube 2˚ only: Cr2O72-, H+, reflux
C KETONE
R1 R2

ROH (anhydrous), reflux

NaBH4, alcoholic or alkaline aq. solution, heat; or LiAlH4 in dry ether

REACTIONS KEY 1˚ only: Cr2O72-, H+, reflux

O
CARBOXYLIC ACID
C
ADDITION LiAlH4 in dry ether R OH
H+ (aq), H2O, reflux
SUBSTITUTION R C N NITRILE
LiAlH4 (ether)

OXIDATION

ROH, conc. H2SO 4 cat.

H2SO 4 & heat

Reflux, H+ or OH -
REDUCTION
P2O5, distil

O
H 2O

ELIMINATION
R NH2
H 2O
AMINE
C ACYL CHLORIDE
HYDROLYSIS R Cl SClO2, PCl3 or PCl5, reflux

ACYLATION O
O
Conc. NH3, room temp. (gives 1˚ amide) ROH, room temp. C ESTER
ESTERIFICATION LiAlH4 (ether) C AMIDE R1 OR2
RNH2, reflux (gives 2˚ amide)
R NH2
OTHER
NH3, reflux (gives 1˚ amide); RNH2, reflux (gives 2˚ amide)

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