CHEM 208 Exam 3

Formaldehyde

Acetaldehyde

Benzaldehyde

Acetone

Acetophenone

Benzophenone

Primary alcohol —> aldehyde

PCC, CH2Cl2 (mild oxidizing agent)

Ozonolysis of alkene —> two ketones or aldehydes

1. O3, 2. DMS

Hydroboration oxidation of terminal alkynes—> aldehyde

1) BHF • THF 2) H2O2, NaOH

Anti markovnikov addition, tautomerization

Hydroboration oxidation of alkenes —> alcohol

1) BHF • THF 2) H2O2, NaOH

Anti markovnikov addition

oxidation of secondary alcohols —> ketones

Mild or strong oxidizing agents

Na2Cr2O7, H2SO4, H2O

Acid catalyzed hydration of terminal alkynes —> ketones

H2SO4, H2O, HgSO4

Markovnikov addition, tautomerization

Acid catalyzed hydration of terminal alkenes —> secondary alcohols

H2SO4, H2O

Markovnikov addition

Carbonyl reduction

Strong: 1) LiAlH4, ether 2) H3O+ work up

Weak: NaBH4, MeOH

Hydride attacks, H3O+ or methanol protonates alkoxide

Ketone hydration —> hydrate (germinal diol)

H3O+ (or water or NaOH H2O)

Depends on wether there’s base or acid sensitive FGs or if you want a prot/deprot product.

Naming aldehydes

Alkane -e to -al

2 aldehydes in alkane = -dial

Adjacent to ring = carbaldehyde

Naming ketones

Alkane -e to -one

Naming carboxylic acids

Alkane -e to -oic acid

2 = -dioic acid

Formic acid

Acetic acid

Propionic acid

Butyric acid

Valeric acid

Benzoic acid

Oxalic acid

Malonic acid

Succinic acid

Glutaric acid

Acid catalyzed acetal formation

H2SO4 or TSOH, ROH —> 2 OR off a carbon