Organic Chemistry Question 1,2 / 1,4 addition

[AMSRebel]

Little unsure as to where to put this thread, but I was hoping somebody could provide me with some insight.

Walked out of my OChem 2 exam today and this was the mechanism (attached below). Basically, we had to outline all the potential products on a cyclohexane conjugated diene reacting with HI.

I ended up writing out 6 products. 4 of which are below attached on the image. The other 2 were if the double bond attacking the hydrogen, placing the charge on the carbon that was too far from the other double bond resulting in no resonance. Would that be correct or are the products only as below? What I was thinking was it'd be possible, but you'd just have low yield so I listed it anyway.

Feeling kinda ****ty right now about my first test results.

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[K9TestRun]

In a conjugated system as the one above, you will get a thermodynamic product and a kinetic product: the 1,4 and 1,2 product. since there are two double bonds, both can attack the H in HBr and form 2 products each. so 4 products total.The addition you listed wouldn't happen due to a disruption in the pi system, where electrons can be shared, making the carbocation more stable.

 

[AMSRebel]

Holy hell, man. Talk about depressing.

My exam logic was although it's incredibly unfavorable, it could still occur. Guess I overthought that one.

Thanks for the response :/

 

[moisne]

Why would you post a OCHEM question here??

Don't you think pre-meds are scarred enough? lol

 

[704]

Why would you post a OCHEM question here??

Don't you think pre-meds are scarred enough? lol

I haven't taken Ochem yet and reading this was terrifying.[/DEADSERIOUS]

 

[moisne]

I haven't taken Ochem yet and reading this was terrifying.[/DEADSERIOUS]

It's not THAT bad.
I did both Ochem 1/2 in a summer... however, I now remember nothing.

If you put a gun to my head and tell me I have 24 hrs to solve a EM physics problem... I may not remember but I can probably rederive most of the equation.

If you put a gun to my head and tell me I have 24 hours to synthesize some compound with it's full mechanism... I'd take the gun and shoot myself. lol