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a ketone (A) which undergo iodoform reaction give compound B on reduction. B on heating with conc H2SO4 give compound C ,which form mono-ozonide D. the compound D on hydrolysis in presence of Zn dust give only acetaldhyde. give reaction and name of A B C D???

a ketone (A) which undergo iodoform reaction give compound B on reduction. B on heating with conc H2SO4 give compound C ,which form mono-ozonide D. the compound D on hydrolysis in presence of Zn dust give only acetaldhyde. give reaction and name of A B C D???

Grade:12

1 Answers

subrat
61 Points
6 years ago
If a ketone gives haloform reaction, then it must have -COCH3 group. The compound is RCOCH3 (say). All we need to do is figure out R (The Alkyl group). After haloform reaction the products are RCOOH + CHX3. RCOOH upon reduction gives RCH2OH (alcohol). Upon dehyration we get cation RCH2+, which forms an alkene (position of double bond is unknown,depends on further information). Now the ozonolysis products is CH3CHO only, so the alkene must be a symmetrical alkene with 4 carbon atoms. CH3CH=CHCH3 is the alkene (must have been obtained after a 1,2 H- shift to form 2nd degree cation). So R is CH3CH2CH2- and the ketone is CH3CH2CH2COCH3.

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