Ochem 2 Final: Synthesis Strategies

Primary alcohol to carboxylic acid

Na2Cr2O7 (H2SO4/H2O)

Acyl chloride, anhydride or ester, amide, nitrile to carboxylic acid

H2O or H3O+

Carboxylic acid to primary alcohol

1) xs LiAlH4 2) H3O+

Carboxylic acid to acyl chloride

SOCl2

carboxylic acid to anhydride

acyl chloride (pyridine)

carboxylic acid to ester

ROH [H+]

acyl chloride to anhydride

carboxylic acid (pyridine)

anhydride to ester

ROH

ester to amide

NH2

amide to nitrile

SOCl2

acyl chloride to ester

ROH (pyridine)

acyl chloride to amide

excess NH2

acyl chloride to aldehyde

1) LiAl(OR)3H 2) H3O+

acyl chloride to primary alcohol

1) excess LiAlH4 2) H3O+

ester to aldehyde

1) DIBAL-H 2) H3O+

ester to primary alcohol

1) excess LiAlH4 2) H3O+

amide to primary amine

1) excess LiAlH4 2) H3O+

nitrile to primary amine

1) excess LiAlH4 2) H3O+

ketone to secondary alcohol

NaBH4 (MeOH)

aldehyde to primary alcohol

1) LiAlH4 2) H3O+

secondary alcohol to ketone

Na2Cr2O7 or CrO3/H3O+ or PCC

primary alcohol to aldehyde

1) CrO3 2) H3O+

aldehyde to carboxylic acid

1) CrO3 2) H3O+

alkene to alcohol

H3O+

ketone to tertiary alcohol

MeMgBr

aldehyde to ketone

1) MeMgBr 2) CrO3/H3O+

alkene to epoxide

RCO3H/MCPBA/1) Br2/H2O 2) NaOH