An organic compound ${{\rm{C}}_5}{{\rm{H}}_{11}}X$ on dehydrohalogenation gives pentene-2 only. What is halide?

${\rm{C}}{{\rm{H}}_3}{\rm{C}}{{\rm{H}}_2}{\rm{CH}}X{\rm{C}}{{\rm{H}}_2}{\rm{C}}{{\rm{H}}_3}$

${\left( {{\rm{C}}{{\rm{H}}_3}} \right)_2}{\rm{CHCH}}X{\rm{C}}{{\rm{H}}_3}$

${\rm{C}}{{\rm{H}}_3}{\rm{C}}{{\rm{H}}_2}{\rm{C}}{{\rm{H}}_2}{\rm{CH}}X{\rm{C}}{{\rm{H}}_3}$

${\rm{C}}{{\rm{H}}_3}{\rm{C}}{{\rm{H}}_2}{\rm{C}}{{\rm{H}}_2}{\rm{C}}{{\rm{H}}_2}{\rm{C}}{{\rm{H}}_2}X$

JEE CHEMISTRY MCQ: HYDROCARBONS

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An organic compound

{\mathrm{C}_5}{\mathrm{H}_{11}}X

on dehydrohalogenation gives pentene-2 only. What is halide?

View answer and explanation

Correct option: A

\mathrm{C}{\mathrm{H}_3}\mathrm{C}{\mathrm{H}_2}\mathrm{CH}X\mathrm{C}{\mathrm{H}_2}\mathrm{C}{\mathrm{H}_3}

Option A (

\mathrm{C}{\mathrm{H}_3}\mathrm{C}{\mathrm{H}_2}\mathrm{CH}X\mathrm{C}{\mathrm{H}_2}\mathrm{C}{\mathrm{H}_3}

) is correct because 3-halopentane will only give pent-2-ene upon dehydrohalogenation due to the symmetrical nature of the molecule.