1.

Compound A treated with NaNH_(2) followed by CH_(3)CH_(2)Br gave compound B. Partial hydrogenation of compound B produced compound C, which on ozonolysis gave a carbonyl compound D, (C_(3)H_(6)O). Compound D did not respond to iodoform test with I_(2) // KI and NaOH. Find ont the structure of C.

Answer»

`CH_(3)-CH_(2)-CH_(2)-CH=CH-CH_(3)`<BR>`CH_(3)-CH_(2)-CH=CH-CH_(2)-CH_(3)`
`CH_(3)-C-=C-CH_(2)-CH_(2)-CH_(3)`
`CH_(3)-CH_(2)-C-=C-CH_(2)-CH_(3)`

Solution :`UNDERSET((A))(CH_(3)CH_(2)C -= CH)underset((II) CH_(3)CH_(2)Br)overset((i) NaNH_(2))to underset((B))(CH_(3)CH_(2)C -= C-CH_(2)CH_(3)) overset("PARTIAL hydrogenation")to underset((c))(CH_(3)CH_(2)CH=CHCH_(2)CH_(3)) underset((ii) Zn+H_(2)O)overset((i) O_(3) "(ozonolysis)")to underset((D))(2CH_(3)CH_(2)CHO) underset((ii) NaOH)overset((i) I_(2) // KI,)to "No iodoform test"`


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