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NEET CHEMISTRYMedium

CH2OHCH2OHCH_2OH \cdot CH_2OH (Ethylene glycol) on heating with periodic acid gives:

A

2CO22CO_2

B

2HCOOH2HCOOH

C

CHOCHOCHO-CHO

D

2HCHO2HCHO

Step-by-Step Solution

The reaction of 1,2-diols (vicinal diols) with periodic acid (HIO4HIO_4) is known as Malaprade oxidation. It involves the oxidative cleavage of the carbon-carbon bond between the two hydroxyl groups.

  1. Mechanism: The reaction proceeds through a cyclic periodate ester intermediate.
  2. Product Prediction: The bond between the carbons bearing the -OH groups breaks. Each -OH group is converted into a carbonyl group (C=OC=O). A primary alcohol group (CH2OH-CH_2OH) becomes Formaldehyde (HCHOHCHO). A secondary alcohol group (CHROH-CHROH) becomes an Aldehyde (RCHORCHO).
  • A tertiary alcohol group (CR2OH-CR_2OH) becomes a Ketone (R2COR_2CO).
  1. Application: Ethylene glycol has the structure HOCH2CH2OHHO-CH_2-CH_2-OH. Both carbon atoms are part of primary alcohol groups. Therefore, the cleavage yields two molecules of Formaldehyde (2HCHO2HCHO). Reaction: CH2OHCH2OH+HIO42HCHO+HIO3+H2OCH_2OH-CH_2OH + HIO_4 \rightarrow 2HCHO + HIO_3 + H_2O.
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