A Level Conversion Map

ORGANIC FUNCTIONAL GROUP INTERCONVERSIONS

Hot, conc. KOH, alcoholic solution

H H R1

C

C

R2

ALKYL HYDROGENSULFATE

R

X

H2O, warm

H OSO3H

HALOALKANE NaOH (aq), reflux

R OH

ALCOHOL

H2SO 4, heat (1˚ alcohols only)

NaBH4 (aq, heat) or LiAlH4 (ether)

R1

O

O

R

C

H

R1

R

N

R

NH2

AMINE

C

R

R

C

R2

ACID ANHYDRIDE

C

OH

C

Cl

ACYL CHLORIDE

CARBOXYLIC ACID

H 2O SClO2, PCl3 or PCl5, reflux

O

O LiAlH4 (ether)

O R

ACYLATION

C

O

H2SO 4 & heat

H 2O

REDUCTION

OTHER

NITRILE

P2O5, distil

OXIDATION

ESTERIFICATION

R2

H+ (aq), H2O, reflux

LiAlH4 (ether)

C

O

KETONE

LiAlH4 in dry ether

SUBSTITUTION

HYDROLYSIS

C

1˚ only: Cr2O72-, H+, reflux

ADDITION

C

O

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

ELIMINATION

R1

Cr2O72-, H+, reflux

ALDEHYDE

2˚ only: Cr2O72-, H+, reflux

REACTIONS KEY

ETHER

R2

O

O

1˚ only: Cr2O72-, H+, distil

KCN, ethanolic solution, reflux Conc. NH3, heat in sealed tube

ADDITION POLYMER

ROH (anhydrous), reflux

Hydrogen halide (aq), room temperature

Polymerisation

EPOXIDE

R2 R4

H2O, reflux

R4

C

ROH, conc. H2SO 4 cat.

ALKENE

O

P2O5, distil

Hydrogen halide & UV light

C

R1 C R3

Reflux, H+ or OH -

R3

H2, Ni cat., 150˚C, 5 atm

H H

C

O2, Ag cat., 250-300˚C, 10-20 atm (ethene only); other alkenes: RCO3H in CH2Cl2

Al2O3, 300˚C, or conc. H2SO 4, reflux

ALKANE

R2

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

R1 C C R2

R1

Cracking (variety of products)

Conc. H2SO 4

H H

NH2

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AMIDE

Conc. NH3, room temp. (gives 1˚ amide)

ROH, room temp.

RNH2, reflux (gives 2˚ amide)

R1

C

OR2

ESTER

NH3, reflux (gives 1˚ amide); RNH2, reflux (gives 2˚ amide)

BY

NC

ND