OCR Synthetic Routes - Lecture notes 1 PDF

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Synthetic Routes: Aliphatic Compounds Alkane

150°C H2/Ni

hydrogen halide 20°C

Alkene

300°C, 60-70atm steam / H3PO4

Haloalkane

dilute KOH/ NaOH, H2O, heat, reflux

conc. H3PO4 or H2SO4, heat 170°C

K2Cr2O7/H2SO4 heat with reflux

NaBH4 water

Amine

K2Cr2O7/H2SO4, reflux

Ketone NaBH4 water

K2Cr2O7/H2SO4 distillation

HCN

HCN

LiAlH4, dilute acid

Hydroxynitrile

Aldehyde K2Cr2O7/H2SO4 reflux

Carboxylic acid

Ester

Carboxylate

H2/Ni

excess ethanolic ammonia/heat

2°

alcohol/conc. H2SO4

OH– heat

Nitrile

sodium halide H2SO4 20°C

Alcohol 1°

carboxylic acid/ conc. H2SO4 OR acid anhydride OR acyl chloride

NaCN/KCN reflux with ethanol

halogen UV

dilute acid, heat dilute alkali, reflux alcohol 20°C

cold H2 O

SOCl2

Acyl chloride

dilute HCl, water, heat, reflux

20°C NH3

primary amine 20°C

1o Amide

2o Amide

Synthetic Routes: Aromatic Compounds NH2 Br2

Sn/conc. HCl

CH3

CH3Cl/ Al Cl3

conc. HNO3 conc. H2SO4 warm

Br2 warm reflux CH3COCl A lCl3

NaBH4

Al Br3 or FeBr3

C l 2/ Al Cl3 or FeCl3 warm

Br

Synthetic Routes: Phenolic Compounds

bromine water, 20°C

2-nitrophenol

&

dilute nitric acid, 20°C NaOH(aq) 20°C

4-nitrophenol

Synthetic Routes: Aliphatic Compounds Alkane Nitrile Alkene

Haloalkane Amine Alcohol 1°

2°

Aldehyde

Ester

Ketone

Hydroxynitrile

Carboxylic acid 1o Amide

Carboxylate

Acyl chloride

2o Amide

Synthetic Routes: Aromatic Compounds NH2

CH3

Br

Synthetic Routes: Phenolic Compounds

OH NO 2

OH

and

OH -

O Na

NO 2

+...