Which of the following compounds will undergo racemization on prolonged digestion of either of its enantiomers with a dilute acid or base?

Options

A. `CH_(3)CH_(2)CHCICH_(3)`
B. `CH_(3)CH_(2)CHBrCH_(3)`
C. `overset(CH_(3))overset(|)(CH_(3)CH_(2)CHCH(CH_(3))_(2)`
D. `CH_(3)CH(OH)COOH`

Answer

D

Explanation

The `C-O` bond is broken and reformed:

The `-OH` of an alcohol is basic and accepts a proton to from the protonated alcohol. When the `C-O` bond of this breaks, one of the products is `H_(2)O`. Since `H_(2)O` is the solvent, there is plenty of it to attack the enantiotopic faces of the flat carboncation `(R^(+))`. These attacks occur with equal probability, resulting in equal amounts of `R` and `S` (a racemicfrom).