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Oxidation of Alcohols

One mole of p...

Question

One mole of polyhydroxy compound A consumes 2 moles of $H I O_{4}$ to produce 2 moles of B and 1 mole of C. B can be converted into C by oxidation with Fehling solution. B gives positive silver mirror test but C does not. Empirical formula of C is $C H_{2} O$ . The molar mass (in g/mol) of A is

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Solution

Lets, analyse the given informations and propose a mechanism as shown below.
As per the question given, B is converted to C so $R$ and $R_{1}$ must be same.
Since the empirical formula of C is $C H_{2} O$ , it will only be true when $R$ is $C H_{3}$ .
So compound A will be 3-methylpent-2,3,4-triol.

Molar mass of A is 134 g/mol.

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