Question 26.SE.6: Name and draw the structural formula for the major product f...
Name and draw the structural formula for the major product formed when 1-methylcyclohexene reacts with HCl. Justify your choice for the major product.
Analyse We are asked for several things here, including knowing something about nomenclature and converting names into structures, as well as the reactivity of alkenes.
Plan Begin by drawing the structure of the reactants and identify the reaction as the addition of HCl to the double bond:
Solve Using Markovnikov’s rule, the hydrogen atom of HX should add to the double bond on the side with the most number of hydrogens:
Hence our answer is 1-chloro-1-methylcyclohexane. Our justification comes from the relative stabilities of the possible carbocation intermediates. Our chosen product forms a 3° carbocation intermediate over the alternative 2° carbocation intermediate because it is more stable due to enhanced inductive effects. To say “because Markovnikov said so” is not satisfactory.