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Q. Compound $A , C _5 H _{10} O _5$, given a tetraacetate with $AC _2 O$ and oxidation of $A$ with $Br _2- H _2 O$ gives an acid, $C _5 H _{10} O _6$. Reduction of $A$ with $HI$ gives isopentane. The possible structure of $A$ is:

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Solution:

(i) Formation of tetraacetete with $Ac _2 O$ means compound $A$ has four $- OH$ linkage.
Reduction of A with $HI$ gives Isopentane i.e. molecule contains five carbon atom.