Which of the following compounds is resistant to oxidation by periodic acid (HIO₄)?
A$$\mathrm{HOCH_2COCH_2OH}$$
B$$\mathrm{HOCH_2CH_2CH_2OH}$$
C$$\mathrm{HOCH_2CH(OH)CH_2OH}$$
D$$\mathrm{HOCH_2CH_2OH}$$
Answer & Solution
Correct answer: B. $$\mathrm{HOCH_2CH_2CH_2OH}$$
Periodic acid cleaves compounds that contain a vicinal diol, or an $\alpha$-hydroxy carbonyl system that can form the required cleavage intermediate.
Option $\mathrm{HOCH_2CH_2OH}$ has two neighboring $\mathrm{-OH}$ groups on adjacent carbons, so it is oxidized.
Option $\mathrm{HOCH_2CH(OH)CH_2OH}$ contains adjacent alcohol groups, so it is oxidized.
Option $\mathrm{HOCH_2COCH_2OH}$ is an $\alpha$-hydroxy ketone equivalent on both sides of the carbonyl and undergoes periodic acid oxidation.
Option $\mathrm{HOCH_2CH_2CH_2OH}$ is a $1,3$-diol, so the hydroxyl groups are not on adjacent carbons and it resists oxidation by periodic acid.
Therefore the correct option is $\mathrm{HOCH_2CH_2CH_2OH}$, which matches option $\mathrm{B}$.
Related questions
Order of boiling points of the given compound is:
(1) pentan-1-ol
(2) butan-1-ol
(3) butaIn the following aromatic compound, bromination in presence of $Fe$ occurs preferentially Given the diazonium salt shown, which product is formed on treatment with $NaNO_2$, Cu andNitrobenzene gives hydroxylamine by-
![](https://qallery.app/diagrams/v2_46c8b1655a73/imgThe correct IUPAC name of the compound,
![](https://qallery.app/diagrams/v2_248e9aa17a93/Which of the following resonating structures of 1-methoxy-1, 3-butadiene is least stable$$\mathrm{CH_3-CH=CH-CH=CH-C_2H_5}$$ isBenzene on treatment with a mixture of conc. $$\mathrm{HNO_3}$$ and conc. $$\mathrm{H_2SO_