When ethyl acetoacetate is reduced with sodium borohydride the reaction yields?

The first biological method involves the reduction of ethyl acetoacetate with baker’s yeast, sucrose, and water into ethyl (S)3-hydroxybutane. The second method involves a chemical reduction utilizing sodium borohydride which yields a racemic mixture of ethyl-3- hydroxybutane.

Why does a reaction of ethyl acetoacetate with sodium borohydride yields a racemic mixture?

Ketones that have different R groups on either side of the carbonyl (achiral) form chiral alcohols. Since both NaBH4 and LiAlH4 are achiral, all reactions produce a racemic mixture. The activation energies leading to each enantiomer are of equal energy, so each will form in the same proportion.

Which one is major product after acidic hydrolysis of ethyl acetoacetate?

Reaction of ethyl acetoacetate with sodium ethoxide followed by addition of benzyl chloride gives an alkylated acetoacetate ester. Subsequent acid-catalyzed hydrolysis with heat leads to decarboxylation of the β-keto acid.

How is NaBH4 prepared?

In the Brown-Schlesinger process sodium borohydride is industrially prepared from sodium hydride (produced by reacting Na and H2) and trimethyl borate at 250–270 °C: B(OCH3)3 + 4 NaH → NaBH4 + 3 NaOCH.

Is ethyl acetoacetate polar?

Ethyl acetate is a polar compound, because the C=O. and C-O bonds are polar and the bond dipole moments don’t cancel each other out.

Is ethyl acetoacetate chiral?

After analyzing the IR and NMR spectra, and the polarimetry data we came to the conclusion that we were successful in reducing ethyl acetoacetate. Our chiral product is the S enantiomer: ethyl (3S)-3-hydroxybutanoate.

How is crotonic acid prepared from ethyl acetoacetate?

Crotonic acid, so named from the fact that it was erroneously supposed to be a saponification product of croton oil, may be prepared by the oxidation of croton-aldehyde, CH3CH:CHCHO, obtained by dehydrating aldol, or by treating acetylene successively with sulphuric acid and water; by boiling allyl cyanide with caustic …

What product is synthesized when vanillin acetate is reduced with NaBH4?

In this lab you will reduce vanillin (4-hydroxy-3-methoxybenzaldehyde) with sodium borohydride (NaBH4) to produce vanillyl alcohol (4-hydroxy-3-methoxybenzyl alcohol), scheme 1.