In the reduction of acetaldehyde to ethanol, the carbonyl carbon acquires a hydrogen atom. Given the polarization of the carbonyl group, it should not be surprising that reagent which delivers the hydrogen to the electron deficient carbonyl carbon delivers it as a hydride ion, :H-. Chemists have developed a multitude of reagents that serve as hydride ion donors. We will consider two, sodium borohydride, NaBH4, and lithium aluminum hydride, LiAlH4. The latter compound is a highly reactive, extremely powerful reducing agent. It is capable of reducing the carbonyl group in aldehydes, ketones, carboxylic acids, esters, amides, and acid halides. NaBH4 is a less reactive, more selective, reagent. It will convert aldehydes and ketones into alcohols, but it will not reduce carboxylic acids, esters, or amides. Equation 1 depicts the reduction of aldehydes and ketones by NaBH4 in general terms. The reaction involves addition of a hydride ion to the carbonyl carbon and transfer of a proton from the oxygen of the solvent to the