Organic Oxidation-Reduction Flashcards
Level 0
alkanes
Level 1
alcohols, alkyl halides, amines
Level 2
aldehydes, ketones, imines
Level 3
carboxylic acids, anhydrides, esters, amides
Level 4
carbon dioxide
Oxidation
loss of electrons, fewer bonds to hydrogens, more bonds to heteroatoms
Reduction
gain of electrons, more bonds to hydrogens, fewer bonds to heteroatoms
Oxidizing Agents
have a high affinity for electrons, or unusually high oxidation states
Reducing Agents
low electronegativities and ionization energies
Oxidation of Primary Alcohol
PCC takes it to an anhydride, stronger will take it to a carboxylic acid
Oxidation of Secondary Alcohol
results in a ketone
Oxidation of Tertiary Alcohol
cannot occur without breaking a carbon-carbon bond
Mesylates and Tosylates
Alcohols can be converted to mesylates (derived from methanesulfonic acid) or tosylates (derived from toluenesulfonic acid) to make them better leaving groups for nucleophilic substitution reactions
Protecting Groups
alcohols can be used as protecting groups for carbonyls, as reaction with a dialcohol forms an unreactive acetal, which can then be reverted after