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Nomenclature of Carbonyls

A ketone A ...

Question

A ketone A $(C_{4} H_{8} O)$ , which undergoes haloform reaction gives compound B on reduction. B on heating with sulphuric acid gives a compound C which forms mono-ozonide D. D on hydrolysis in presence of zinc dust gives only acetaldehyde E. Identify A, B, C, D and E. Write the reactions involved.

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Solution

A Ketone $A (C_{4} H_{8} O)$ undergoes haloform reaction, So the Ketone should have $- C ∥ - {C H}_{3}$ group.
$O$
So the structure of $A$ is ${C H}_{3} - {C H}_{2} - C ∥ - {C H}_{3}$ .
$O$
Now the reactions are :
A (butane $- 2 -$ ene) on reduction gives butan $- 2 - o l$
(B) Which on heating with $H_{2} {S O}_{4}$ gives a alkene named but $- 2 -$ ene (C). $C$ forms mono-ozonide $D$ which on hydrolysis in presence $Z n$ dust to form acetaldehyde $(E)$ .

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