[HusamEddin]

Hi everybody wanna ask U please

adding two moles of HCl to 1,4-hexadiene
C=C-C-C=C-C + 2HCl

will give me only one product ,, or 2 products I'm really confused look the first step is unclear to me ...
when adding the first mole of HCl
H+ + Cl-
what bond will we break first ? bond on carbon 1 or that on carbon 4 ? -this is my first Question-
assuming we started by breaking bond number 1 ,,, the Hydrogen (according to Markovnikov's rule) will bind to the carbon number 1 ,, it is clear but if we started by breaking the other bond ,, where to put the Hydrogen , Carbon 4 or 5 ? they are the same to me if I want to follow Marko's rule ,,, but if done ,, this will give me a 2 products with different structures

would you help me please ?

*{MOD EDIT - remove white space}*

[Schrödinger]

Practially when you do this in the lab, you will not be happy with what you see. You will get atleast 3 to 4 products. Onechlorinated at (1,4), another at (2,4), (1,5), (2,5), some monochlorinated, etc.
It's not a neat reaction at all. And since C-4 and C-5 aren't a lot different, the ratio of chlorination on 4 and 5 will be close to 1. Once again, this depends on whether the other site reacts first, and if so which C gets chlorinated (1 or 2), etc.