Question

Draw the primary alcohol with molecular formula C5H12O that cannot be synthesized by the hydroboration–oxidation of an alkene.

Answer 1

The answer is neopentyl alcohol. (CH₃)₃C-CH₂-OH

Step-by-step explanation:

This alcohol cannot be synthesized by the hydroboration–oxidation of an alkene since the reaction of hydroboration–oxidation go through steps that involved the addition of BH₃ into the original structure. In the case of neopentyl alcohol, if we carry out retro synthetic by the hydroboration–oxidation, we will find the original alkene is (CH₃)₃C=CH₂ which is impossible since the center carbon atom has 5 bonds.

The condition for hydroboration–oxidation reaction is that the alkene must have the structure of R-CH=CH₂