1. Tardigrade
  2. Question
  3. Chemistry
  4. An unknown alkyl halide [ X ] reacts with alcoholic KOH and produces a hydrocarbon ( C 4 H 8) as the major product. Ozonolysis of this hydrocarbon affords one mole of propanaldehyde and one mole of formaldehyde. Suggest which organic compound among the following has the correct structure of the above alkyl halide [ X ] ?

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Q. An unknown alkyl halide $[ X ]$ reacts with alcoholic $KOH$ and produces a hydrocarbon $\left( C _{4} H _{8}\right)$ as the major product. Ozonolysis of this hydrocarbon affords one mole of propanaldehyde and one mole of formaldehyde. Suggest which organic compound among the following has the correct structure of the above alkyl halide $[ X ]$ ?

ManipalManipal 2015

Solution:

As the ozonolysis gives propanaldehyde and formaldehyde thus the hydrocarbon is $\underset{\text{1-butene}}{CH _{3} CH _{2} CH} = CH _{2}\left( C _{4} H _{8}\right)$
1-butene can be obtained by $CH _{3}- CH _{2}- CH _{2}- CH _{2}- Br \xrightarrow[-HBr]{Alc.KOH}CH _{3} CH _{2} CH = CH _{2}$.