Question

Consider the following compound with the molecular formula C4HgO2 OH a. Draw a constitutional isomer that you expect would be approximately one trillion (10) times more acidic than the compound above. What explains the increased acidity of this isomer? Draw a constitutional isomer that you expect will be less acidic than the compound above. Why would the acidity be decreased? b. Draw a constitutional isomer that you expect will have approximately the same pKa as the compound above. c. d. Draw a set of stereoisomers with the same molecular formula (CaHyO2). What is their relationship to the compound above?
Please answer all questions correctly especially question d. Also, explain if you can!

Answer 1

a. A constitutional isomer that should be approximately one trillion times more acidic than the given compound is,

он он oxetan-3-ylmethanol butyric acid

This is so because the main functional group of the given compound is alcohol, where butyric acid has -COOH group, hence it is more acidic and it can easily give H⁺ in aqueous solution and its conjugate base is also stable.

b. A constitutional isomer that should be less acidic than the given compound is,

он oxetan-3-ylmethanol ethyl acetate

Here ethyl acetate molecule does not have an acidic proton attached to a more electronegative atom. Hence it will not give proton easily and thus it is less acidic in nature.

c. A constitutional isomer that should have approximately the same pK_a is,

он он tetrahydrofuran-3-ol oxetan-3-ylmethanol

Both have similar functional groups, hence pK_a should be more or less the same.

d. A set of stereoisomers with the same molecular formula C4H8O2 are,

он ОН (S)-tetrahydrofuran-3-ol(R)-tetrahydrofuran-3-ol

These two isomers are constitutional isomers of the given molecule.