Which of the following compounds does not undergo oxidative cleavage with periodic acid?

Options

A.
B.
C.
D.

Answer

D

Explanation

Compounds that have hydroxyl group on adjacent atoms undergo oxidative cleavage when they are treated with aqueous periodic acid `(HIO_(4))`. The reaction breaks carbon-carbon bonds are produce carbonyl compounds (aldehydes, ketones, or acids). The stoichiometry of the reaction is
Since the reaction usually takes place in quantitative yield, valuable infomation can often be gained by measuing the number of molar equivalents of periodic acid that is consumed in the reaction as well as by identifying the carbonyl products.
The reagent lead tetracetate, `Pb(O_(2) C CH_(3))_(4)`, brings about cleavage reactions similar to those of periodic acid. The two reagents are complementary as periodic gives good results in organic solvents.
Periodate oxidations are thought to take plane place through a cyclic intermediate:
Notice that in the these periodate oxidations, a `C == O` bonds is formed at each carbon, for every `C - C` bond broken.
(A) When three or more `-CHOH` groups are contiguous, the internal ones are obtained as formic acid. For example, periodate oxidation of glycerol gives tow molar equivlents of formaldehyde and one molar equivalent of formic acid.
(B) Oxidative cleavage also takes place when an `-OH` group is adjacent to carbonyl group of an aldehyde or ketone (but not that of an aicd a or an ester). Thus, glyceraldehyde yields two molar equivalents of formic acid acid and one molar equivalent of formaldehyde:
One the other hand, dihydroxyacetone gives two molar equivalents of formaldehyde and one molar equivalent of carbon dioxide:
(C ) Periodic does not cleave compounds in which the hydroxyl groups are separated by an intervening `-CH_(2)-` group, nor those in which a hydroxyl group is adjacent to an ether of acetlyl function: