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Standard XII

Chemistry

Sulphur

An organic co...

Question

An organic compound $A$ has molecular formula $C_{5} H_{10} O$ and it neither decolourise bromine water solution nor evolve any gas on heating with $N a$ -metal. $A$ on refluxing with aqueous $H I$ yields $B (C_{5} H_{10} I_{2})$ which is non-resolvable. $B$ on treatment with $N a C N$ in acetone yield $C (C_{5} H_{10} I N)$ in significant amount while $B$ on treatment with aqueous $H_{2} O$ yields $D (C_{5} H_{11} I O)$ in significant amount. $D$ does not change the orange colour of acidic dichromate solution. Deduce structures of $A$ to $D$ .

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Solution

Let us understand the importance of the given data:
It does not decolorize $K_{2} C r_{2} O_{7} ⟶ E t h e r$ this is confirmed with $B r_{2} / H_{2} O$ which indicates there is no double bond present.
Only one $I$ -group is substituted so the compound is asymmetric.

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Let us understand the importance of the given data:It does not decolorize K2Cr2O7⟶Ether this is confirmed with Br2/H2O which indicates there is no double bond present.Only one I-group is substituted so the compound is asymmetric.

Let us understand the importance of the given data:
It does not decolorize $K_{2} C r_{2} O_{7} ⟶ E t h e r$ this is confirmed with $B r_{2} / H_{2} O$ which indicates there is no double bond present.
Only one $I$ -group is substituted so the compound is asymmetric.