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An organic compound (A) (C(8)H(14)O) for...

An organic compound (A) `(C_(8)H_(14)O)` forms an oxime and gives a positive haloform reaction. On ozonolysis, it gives acetone and a compound (B) `(C_(5)H_(8)O_(2))` . (B) forms a dioxime and on subjecting to oxidation reaction gives an acid (C ) `(C_(4)H_(6)O_(4))`. On treatment with excess of ammonia and strong heating, (C ) gives a neutral compound (D) `(C_(4)H_(5)O_(2)N)`. (D) on distillation with zinc dust forms pyrrloe. Suggest the possible structures of (A), (B), (C ), and (D). Explain the chemical reactions involved.

Text Solution

Verified by Experts


Structure of (B):
i. On oxidation, one is lost, so (B) must contain a `(Me-overset(O)overset(||)C-)` group and aldehyde group.
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CENGAGE CHEMISTRY-ALIPHATIC AND AROMATIC ALDEHYDES AND KETONES-Exercises Subjective
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  2. Complete the following reaction

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  3. Convert HCHO to glycol in one step only.

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  4. Convert and vice versa.

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  5. Convert benzence to PhCHO in one step only.

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  6. An aromatic kentone (X) has the molecular formula C(10)H(12)O(2). On v...

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  7. A natural compound (A) (C(7)H(6)O) forms an oxime. When (A) is treated...

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  8. An organic compound (A) (C(8)H(14)O) forms an oxime and gives a positi...

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  9. Compound (A) (C(6)H(12)O(2)) on reduction with LiAlH(4) yielded two co...

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  10. Hydrocarbon (X), C(7)H(12), on reaction with boron hydride followed by...

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  11. An organic compound (A) (C(6)H(10)) on reaction with CH(3)MgBr followe...

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  13. A 0.535 gm mixture of ethanol and acetaldehyde when heated with Fehlin...

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  14. An orgnic compound (A) contains 79.25% C, 5.66% H, and 15.09% O. It ha...

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  15. An organic compound (A) containing 60.12% (C ) and 13.3% H has vapour ...

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  16. Two organic compounds (A) and (B) containing 62.01% C and 10.3% H reac...

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  17. An organic compound (A) (C(5)H(7)OCl) reacts rapidly with ethanol to g...

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  18. An organic compound (A) contains 87.27% C and 13.73% H. Its vapour den...

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  19. An organic compound (A) C(4)H(9)Cl on reacting with aqueous KOH gives ...

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