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An alkyl bromide A has molecular formula...

An alkyl bromide A has molecular formula `C_(8)H_(17)Br` and four different structures can be drawn for it, all optically active. A on refluxing with ethanolic `KOH` solution yields only one elimination product `B(C_(8)H_(16))` which it still enantiomeric. B on treatment with `H_(2)//Pt` yields `C(C_(8)H_(18))` which does not rotate the plane polarized light, B on ozonolysis followed by work-up with `H_(2)O_(2)` yields `D(C_(7)H_(14)O)` as one product which it still resolvable. Deduce structures of A to D.

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The correct Answer is:
`(##ALN_CHM_C08_E01_089_A01##)`
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An organic compound A has molecular formula C_(10)H_(17)Br and it is non-resolvable. A does not decolourise brown colour of bromine water solution. A on treatement with (CH_(3))_(2 COK//(CH_(3))_(3)COH yields B as majot product. B on treatment with H_(2)//Pt yields (C_(10)H_(16)) which on treatment with CI_(2)//hv yields three monochloro derivative. Also B on boiling with acidic permanganate solution yields C(C_(10)H_(16)O_(3))C . on heating with sodalime yields D(C_(9)H_(16)O).D on reducing with LiAIH_(4) followed by heating product with concentrated H_(2)SO_(4) yields E(C_(9)H_(16)) as major product. E on treatment with ozone followed by work-up with Zn-H_(2)O yields 6-Ketononanal. Compound B is:

An organic compound A has molecular formula C_(10)H_(17)Br and it is non-resolvable. A does not decolourise brown colour of bromine water solution. A on treatement with (CH_(3))_(2 COK//(CH_(3))_(3)COH yields B as majot product. B on treatment with H_(2)//Pt yields (C_(10)H_(16)) which on treatment with CI_(2)//hv yields three monochloro derivative. Also B on boiling with acidic permanganate solution yields C(C_(10)H_(16)O_(3))C . on heating with sodalime yields D(C_(9)H_(16)O).D on reducing with LiAIH_(4) followed by heating product with concentrated H_(2)SO_(4) yields E(C_(9)H_(16)) as major product. E on treatment with ozone followed by work-up with Zn-H_(2)O yields 6-Ketononanal. Compound D is:

An organic compound A has molecular formula C_(10)H_(17)Br and it is non-resolvable. A does not decolourise brown colour of bromine water solution. A on treatement with (CH_(3))_(2 COK//(CH_(3))_(3)COH yields B as majot product. B on treatment with H_(2)//Pt yields (C_(10)H_(16)) which on treatment with CI_(2)//hv yields three monochloro derivative. Also B on boiling with acidic permanganate solution yields C(C_(10)H_(16)O_(3))C . on heating with sodalime yields D(C_(9)H_(16)O).D on reducing with LiAIH_(4) followed by heating product with concentrated H_(2)SO_(4) yields E(C_(9)H_(16)) as major product. E on treatment with ozone followed by work-up with Zn-H_(2)O yields 6-Ketononanal. Compound C is:

An organic compound A has molecular formula C_(10)H_(17)Br and it is non-resolvable. A does not decolourise brown colour of bromine water solution. A on treatement with (CH_(3))_(2 COK//(CH_(3))_(3)COH yields B as major product. B on treatment with H_(2)//Pt yields (C_(10)H_(16)) which on treatment with CI_(2)//hv yields three monochloro derivative. Also B on boiling with acidic permanganate solution yields C(C_(10)H_(16)O_(3))C . on heating with sodalime yields D(C_(9)H_(16)O).D on reducing with LiAIH_(4) followed by heating product with concentrated H_(2)SO_(4) yields E(C_(9)H_(16)) as major product. E on treatment with ozone followed by work-up with Zn-H_(2)O yields 6-Keto nonanal. Compound A is: