Question

Orgo II Tutorial: Alcohol Reactions

Answer 1

\({\bf{Reduction~of~Carbonyls:}}\)
> LiAlH4. will reduce esters, carboxylic acids, aldehydes, ketones
> LAH (strong reducing agent, reacts violently, produces H2, so not the most desirable unless there is no other choice)
> NaBH4 (preferred reagent for reducing aldehydes/ketones). not strong enough for esters or carboxylic acids

Answer 2

LiaLH4 can also be used to replace halide with a hydrogen

Answer 3

\({\bf{Oxidation~of~Carbonyls:}}\)
*** note: this requires a hydrogen on the alcohol carbon to occur ***
basic mechanism:



aldehydes can also be oxidized, albeit through a different mechanism involving addition of water to form an aldehyde hydrate

Answer 4

\({\bf{Swern~Oxidation:}}\) synthesizes alcohols from aldehydes and ketones, using DMSO and COCl2 at low temperatures + Et3N

Answer 5

\({\bf{Chromic~Acid~Oxidation:}}\) follows a similar mechanism (addition of leaving group and electron pushing to form a ketone)

Answer 6

the mechanism is beyond the scope of this class but PCC + CH2CL2 will oxidize a primary alcohol into an aldehyde and a secondary alcohol into a ketone

Answer 7

Anyway, that's the end of my tutorial, I hope it was a helpful resource. Source material is Organic Chemistry 12th edition by Solomons, et. al.