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Formation of Enamines

Compound X C,...

Question

Compound (X) (C, H, O) gives a red precipitate with cupric ions in basic medium. This compound on keeping in excess of acetic acid with some catalyst forms a polyacetal (Y). (Y) does not respond to $C u^{2 +} / O H$ . (X) on $H I O_{4}$ oxidation forms formic acid (4 moles) and formaldehyde (1 mole only). With $P h N H N H_{2} / H C l$ , forms red coloured product (Z). By consuming 2 moles of the $P h N H N H_{2} / H C l$ , (Z) is also obtained by the given compound (W).
The compound (Y) does not give a positive test with $C u^{2 +} / O H^{-}$ , because:

A

it has cyclic hemiacetal structure

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B

it has cyclic acetal type of structure which does not tautomerise into acyclic form

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C

it is an acyclic polyacetate and does not have any aldehydic group

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D

it is a ketone

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Solution

The correct option is B it has cyclic acetal type of structure which does not tautomerise into acyclic form
Since 'Y' does not give a positive test with $C u^{2 +} / O H^{-}$ (Felling's test). Therefore, it should not contain any aldehyde and ketone functional group.
Therefore 'Y' must have cyclic polyacetal structure which does not tautomerise into acylic form.

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