What would be the product when 2,3-dimethylhexanoic acid is treated with SOCl2/pridine, followed LiAl [OC(CH3)3]3H ?

1 Answer
Mar 21, 2016

The dialdehyde results: H(O=C)CH(CH_3)CH(CH_3)CH_2CH_2C(=O)H

Explanation:

"Diacid + thionyl chloride "rarr" Diacid halide + sulfur dioxide"

"Diacid halide + hydride transfer reagent "rarr" Dialdehyde"

Li^+[HAl(OBu^t)_3]^- is a hydride transfer reagent that delivers 1 hydride instead of the 4 that lithium aluminum hydride (LiAlH_4) delivers. it will react with acid halides to give the formyl species, the aldehyde:

"Diacid halide + hydride transfer reagent" rarr "Dialdehyde + lithium chloride"