Chemistry 3BL

MechRocket
Wed, 12 May 2010 02:59:28 +0000

NaBH4 doesn’t do crap to either esters (no reaction at all) or carboxylic acids (simply deprotonates)

LAH does though, to carboxylic acids it will generate the dianion and then the O2- will leave forming an aldehyde, which then gets further attacked by H-; then for esters, it will attack and then kick out the OR leaving group, which generates another aldehyde and gets attacked again.