CHM 228H Ch 12 Oxidation + Reduction

LAH reduces carboxylic acids and esters to ______ _______

primary alcohols

Primary alcohols can be oxidized to

aldehydes to carboxylic acids

secondary alcohols can be oxidized to

ketones

Tertiary alcohols cannot be

oxidized

Primary alcohol ---> aldehyde

1.) PCC

2.) CH2Cl2

Primary alcohol ---> carboxylic acid

H2CrO4 or 1). KMnO4 2.) H3O+

Secondary alcohol ---> ketone

1.) PCC 2.) CH2Cl2

or

H2CrO4

or

1.) KMnO4 2.) H3O+

Aldehyde/ketone ---> alcohol + Nu

1.) R-MgBr

2.) H3O+ or (NH4+)

Ester + R-MgBr 2) H3O+ =

Alcohol + 2 Nu + R

Epoxide + R-MgBr 2). H3O+ =

Alcohol + Opposite side Nu

Ester --> primary alcohol

LAH, H3O+

Carboxylic acid ---> primary alcohol

LAH, H3O+

Aldehydes ---> primary alcohol

LAH or NaBH4 2). H3O+

Ketone --> secondary alcohol

LAH or NaB4 2). H3O+