Which of the following alkenes cannot be prep | vedclass

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(D) The reaction of $n-butylamine$ $(CH_3-CH_2-CH_2-CH_2-NH_2)$ with $NaNO_2/HCl$ produces a diazonium salt,which loses $N_2$ to form a primary carboc

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$Iso-butene$

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(D) The reaction of $n-butylamine$ $(CH_3-CH_2-CH_2-CH_2-NH_2)$ with $NaNO_2/HCl$ produces a diazonium salt,which loses $N_2$ to form a primary carbocation: $CH_3-CH_2-CH_2-CH_2^+$.This primary carbocation undergoes a $1,2-hydride$ shift to form a more stable secondary carbocation: $CH_3-CH_2-CH^+-CH_3$.Elimination of a proton from the primary carbocation yields $1-butene$.Elimination of a proton from the secondary carbocation yields both $cis-2-butene$ and $trans-2-butene$.$Iso-butene$ $(2-methylpropene)$ cannot be formed because it would require a carbon skeleton rearrangement (branching),which does not occur in this simple $1,2-hydride$ shift.

Which of the following alkenes cannot be prepared by the deamination of $n-butylamine$ $(n-BuNH_2)$ with $NaNO_2/HCl$?

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