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(D) The reaction proceeds in two steps: $1$. Electrophilic addition of $HCl$ to $1$-methylcyclohex-$1$-ene follows Markovnikov's rule. The proton $(H^

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$1-$methyl$-1-$nitritocyclohexane

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(D) The reaction proceeds in two steps: $1$. Electrophilic addition of $HCl$ to $1$-methylcyclohex-$1$-ene follows Markovnikov's rule. The proton $(H^+)$ adds to the carbon with more hydrogens,and the chloride ion $(Cl^-)$ adds to the more substituted carbon (the one with the methyl group),forming $1$-chloro-$1$-methylcyclohexane. $2$. The reaction of $1$-chloro-$1$-methylcyclohexane with $AgNO_2$ is a nucleophilic substitution reaction ($S_N1$ mechanism). The $Cl^-$ is replaced by the nitrite group $(-ONO)$ or nitro group $(-NO_2)$. Since $AgNO_2$ is an ionic reagent,it primarily acts as a source of nitrite ions $(NO_2^-)$,which can bond through oxygen to form a nitrite ester $(-ONO)$ or through nitrogen to form a nitro compound $(-NO_2)$. In the case of tertiary alkyl halides,the formation of the nitrite ester $(-ONO)$ is often the major product due to the ambident nature of the nitrite ion and the stability of the tertiary carbocation intermediate. Thus,the major product is $1$-methyl-$1$-nitritocyclohexane.

Identify the major product formed from the following reaction: $1$-methylcyclohex-$1$-ene $\xrightarrow[(ii) AgNO_2]{(i) HCl} ?$

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