InterviewSolution
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InterviewSolution
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A compound (A) having molecular formula C_4H_9Cl, on heating with alcoholic KOH solution, gives two isomeric alkenes (B) & (C ) . The mixture of (B) & ( C) ,on ozonolysis produces three compounds : 1 HCHO, 2CH_3CHO, 3 CH_3CH_2CHO. Ascertain structures of (A) , (B) and ( C) . |
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Answer» SOLUTION :The compound (A), when heated with alcoholic KOH solution, undergoes dehydrochlorination to give two isomeric alkenes (B) and (C ). So the molecular formula of these two alkenes is `C_4H_8` . `C_4H_9Cl (A) overset("Alcoholic KOH")underset("heat") to C_4H_8(B)+C_4H_8(C )` Mixture of (B) and (C ) on, OZONOLYSIS, produces three carbonyl COMPOUNDS `(HCHO,CH_3CHO &CH_3CH_2CHO)`. Now, the TOTAL number of carbon atoms of the compound or compounds obtained by ozonolysis must be equal to the number of carbon atoms present in the compoundundergoing ozonolysis. so , let us suppose that as a result of ozonolysis of the alkene B ,1 molecule of `CH_3CH_2CHO`and 1 molecule of HCHO (total number of carbon atomsof the two compounds = 4) are obtained and the ozonolysis of ( C) produces 2 molecules of `CH_3CHO` (total number of carbon atom of the two molecules =4 ) . So, the structure of the alkene B is `CH_3CH_2CH=CH_2` (1-butene) & the structure of alkene C is `CH_3CH=CHCH_3` (2-butene). `[{:(CH_3CH_2CH=O+O=CH_2rArrCH_3CH_2CH=CH_2),(CH_3CH=O+O=CHCH_3rARrCH_3CH=CHCH_3):}]` Since the compound (A) on dehydrochlorination, produces 1-butene and 2-butene, the structure of (A ) is: `CH_3CH_2CH(Cl)CH_3` (2-chlorobutene) 
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