Preparations of Aldehydes, Ketones and Carboxylic Acids

PCC (or DMP), CH2Cl2

OR

1) DMSO, (COCl)2

2) Et3N

Oxidation of primary alcohol to aldehyde

1) R2B-H

2) H2O2, NaOH

anti-markovnikov Hydroboration - oxidation of terminal alkyne to aldehyde

(secondary OH)

Na2Cr2OH

H2SO4, H2O

Oxidation of secondary alcohol to ketone

H2SO4, H2O

HgSO4

markovnikov acid-catalyzed hydration of terminal alkyne to ketone

RCOCl

AlCl3

Friedel-crafts acylation of benzene to aryl ketone

(primary OH)

Na2Cr2OH

H2SO4, H2O

Oxidation of primary alcohol to aldehyde

(alkylbenzene)

Na2Cr2O7

H2SO4, H2O

Oxidation of alkylbenzene to carboxylic acid

(alkyne)

1) O3

2) H2O

Oxidative cleavage of alkynes to form carboxylic acids

(alkene)

1) O3

2) DMS

Ozonolysis of alkenes to aldehydes and ketones (check for presence of hydrogens to determine)