Ch 20 Reagents

1. NaCN

2. H3O+, heat

alkyl halide to carboxylic acid

1. Mg

2. CO2

3. H3O+

alkyl halide to carboxylic acid

1. xs LiAlH4

2. H3O+

reduces carboxylic acid

BH3 * THF

reduction of carboxylic acid selectively

SOCl2, pyr

carboxylic acid to acid chloride

H2O, pyr

acid chloride to carboxylic acid

xs NH3

acid chloride to amide

xs RNH2

acid chloride to amide

1. xs LiAlH4

2. H2O

reduction of acid chloride

1. LiAl(OR)3H

2. H2O

acid chloride to aldehyde

1. xs RMgBr

2. H2O

adds R groups to acid chloride, replaces with alcohol

R2CuLi

acid chloride to ketone

ROH, pyr

acid chloride to ester

1. NaOH

2. CH3COCl

carboxylic acid to acid anhydride

heat

carboxylic acid to acid anhydride

H2O

acid anhydride to carboxylic acid

1. NaOH

2. CH3I

carboxylic acid to ester

[H+], MeOH

carboxylic acid to ester

NH3

ester to amide

1. DIBAH

2. H2O

ester to aldehyde

1. NaOH, heat

2. H3O+

ester to carboxylic acid

H3O+

ester to carboxylic acid

1. xs LiAlH4

2. H2O

(amide)

reduces amide to amine

1. NaOH, heat

2. H3O+

(amide)

amide to carboxylic acid

H3O+

(amide)

amide to carboxylic acid

NaCN

alkyl halide to nitrile

SOCl2

amide to nitrile

H3O+ (nitrile)

nitrile to carboxylic acid

1. NaOH, heat

2. H3O+

(nitrile)

nitrile to carboxylic acid

1. RMgBr

2. H3O+

(nitrile)

nitrile to ketone

1. xs LiAlH4

2. H3O+

(nitrile)

nitrile to amine reduction

1. KOH, H2O, heat

2. H2O, H2SO4

nitrile to carboxylic acid

P4O10

amide to nitrile