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JEE Advanced levelNumerical answerDifficulty 3 of 3ro259

The compound shown is treated with excess periodic acid. Assume that every carbon-carbon bond joining two carbons that each carry an oxygen function (hydroxyl or carbonyl) is cleaved, using one mole of $HIO X_{4}$ per bond cleaved. How many moles of $HIO X_{4}$ are consumed per mole of the compound? Give the answer as an integer.

Numerical answer type, tolerance 0.5.

Answer: 4

The compound is a pentulose (a 2-keto-pentose, five carbons all oxygenated). All four C-C bonds link adjacent oxygenated carbons (

CH X_{2} OH - C (= O)

,

C (= O) - CHOH

,

CHOH - CHOH

,

CHOH - CH X_{2} OH

), so four cleavages occur and 4 mol of

HIO X_{4}

are used (counted by substructure search).

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