Question

Draw the products obtained from the reaction of 1 equivalent of HBr with 1 equivalent of 2,5-dimethyl-1,3,5-hexatriene. Draw the molecules on the canvas by choosing buttons from the Tools (for bonds and charges), Atoms, and Templates toolbars

Answer 1

Here's what I get.

Step-by-step explanation:

According to Markovnikov's rule, the H will add to a terminal carbon, generating three resonance stabilized carbocations.

The Br⁻ ion will add to any of the three carbocations.

There are three possible products:

1. 5-bromo-2,5-dimethylhexa-1,3-triene (1)
2. 3-bromo-2,5-dimethylhexa-1,4-triene (2)
3. 1-bromo-2,5-dimethylhexa-2,4-triene (3)