Chem 51C: Ch.17 - Carbonyls, Organometallics, Oxidation & Reduction

what do aldehydes/ketones get reduced to

alcohols

what do carboxylic acids reduce to

aldehydes and primary alcohols

what do aldehydes oxidize to

carboxylic acids

what does NaBH4 and LiAlH4 do for aldehydes and ketones

aldehyde — primary alcohol

ketone — secondary alcohol

Note: LAH is harsh

what does H2/Pdc do for aldehydes and ketones

aldehyde — primary alcohol

ketone — secondary alcohol

what does LiAlH4 do for acid chlorides, esters, CA

convert to alcohols

what does LiAlH4 do for amides

converts to amines

what does LAH[OC(CH3)3]3 for acid chlorides

convert to aldehydes

what does DIBAL—H do for esters

convert to aldehyde

what are the types of organometallic reagents

1. R—Li

2. RMgX

3. R2CuLi

how does organometallic reagents react as a nucleophile

1. aldehydes/ketones — alcohol

2. carboxylic acids — ketones/alcohols

what is the protecting group process

1. protect

2. run desired reaction

3. deprotect

what is an example of a PG

1. TDMS

2. pTsOH

how to organometallic reagents react w/ CA

adds to carbonyl group and creates an OH

organo w/ CO2 gives…

carboxylic acids

organo w/ epoxides gives…

opens epoxide ring into carbon chain