This is a question from my textbook:
Why does the alkylation of benzene with 1-chloropropane give (propan-2-yl)benzene and not (propan-1-yl)benzene?
The book shows the reaction with chloromethane and chloroethane, and there is no such ambiguity in the two cases as the obvious products are methylbenzene and ethylbenzene respectively.
Is there a rule which I need to know in order to figure out which substituted benzene of the two would be more stable? Up till now I've only encountered Markovnikov's rule, Kharash/peroxide effect, Zaitsev's rule and Popoff's rule in the book; none of these seem to be applicable in this case.