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Question 67 of 76

Q.HO−CH2−CH2−OHHO-CH_2-CH_2-OH on heating with periodic acid gives :

(a) Methanal
(b) Methanoic acid
(c) CO2CO_2
(d) Glyoxal
Puducherry TnboardTamil Nadu HSC (DGE) Board 2022MCQ· 1mImportance★★★★★
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Periodic acid cleaves the C–C bond of the vicinal diol HO−CH2−CH2−OHHO-CH_2-CH_2-OH, converting each −CH2OH-CH_2OH carbon into −CHO-CHO, so the product is methanal (HCHO); HIO4HIO_4 itself is reduced to HIO3HIO_3.

The general reaction of a 1,2-diol with periodic acid is R2C(OH)−C(OH)R2′+HIO4→R2C=O+R2′C=O+HIO3+H2OR_2C(OH)-C(OH)R_2' + HIO_4 \rightarrow R_2C=O + R_2'C=O + HIO_3 + H_2O, cleaving the bond between the two hydroxyl-bearing carbons. For ethylene glycol, HO−CH2−CH2−OHHO-CH_2-CH_2-OH, both carbons are −CH2OH-CH_2OH (each bearing 2 H, 1 OH, and the C–C bond to be cleaved), so cleavage converts each into H2C=OH_2C=O, i.e. methanal. No further oxidation to methanoic acid or CO2CO_2 occurs under these specific cleavage conditions, and glyoxal (OHC–CHO) would only …

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