Anti-Markovnikov

I've got a question about this molecule http://www.chemspider.com/Chemical-Structure.557853.html
How would I explain the product that would be obtained if HCL was added and the Cl bonds to the less substituted C?

Reply 1

adsuudixfra

7

two intermediates can form when the H+ joins, one where carbon 2 (of the pentene chain) accepts the H, and one where carbon 3 accepts it. the carbon with the most hydrogens (carbon 2) is most likely to accept it, so the major intermediate has a positive charge on carbon 3 which then forms a bond with the Cl-

Reply 2

jordanwu

OP

13

Original post by adsuudixfra

two intermediates can form when the H+ joins, one where carbon 2 (of the pentene chain) accepts the H, and one where carbon 3 accepts it. the carbon with the most hydrogens (carbon 2) is most likely to accept it, so the major intermediate has a positive charge on carbon 3 which then forms a bond with the Cl-

Hmm, I know about the major product but what about the other one where the Cl- bonds to carbon 2 instead? I've been asked to explain the regioselectivity but I'm not sure about this one, only that it's Anti-Markovnikov

Reply 3

adsuudixfra

7

Original post by jordanwu

Hmm, I know about the major product but what about the other one where the Cl- bonds to carbon 2 instead? I've been asked to explain the regioselectivity but I'm not sure about this one, only that it's Anti-Markovnikov