orgo question

[mgdent]

Advertisement - Members don't see this ad

hi guys, in the chair configuration of cyclohexane, if you had an OH group and t-butyl on the same C, which would be equatorial? Basically, when you have 2 groups on the same C, which is axial and which is eq? I know eq is favored so the more bulky hindered group is eq but i havent seen them on the same carbon.

 

[BRM3488]

I'm not sure if they would be on the same C due to steric hindrance. But if they are, I would go with the general rule of larger in eq, smaller in ax.

Just a guess though.

 

[Baylor2011]

Unlikely to find two large groups on the same carbon, that'd be more of a reaction intermediate type thing...but just hypothetically I'd say the t-butyl group would be equatorial

 

[LaFleur]

If there were two groups on the same carbon, the bulkier group should be equatorial more often.

Sent from my ADR6300 using Tapatalk

 

[DQLEUCD]

hi guys, in the chair configuration of cyclohexane, if you had an OH group and t-butyl on the same C, which would be equatorial? Basically, when you have 2 groups on the same C, which is axial and which is eq? I know eq is favored so the more bulky hindered group is eq but i havent seen them on the same carbon.

t-butyl has equitorial priority, check chads vids, he has a great explanation for it