-1
$\begingroup$

enter image description here

enter image description here

Compare the acidities and basicities of the compounds in the first and second row respectively.

In aromatic compounds the methyl group would cause an "ortho" effect. Here we don't have an aromatic compound. Would there still be something like an ortho effect?

$\endgroup$
2
  • 2
    $\begingroup$ I think you can answer your own question if you look at the reasons behind the ortho effect in aromatic compounds. $\endgroup$
    – Zhe
    Commented May 23, 2020 at 13:33
  • $\begingroup$ We could assume ring flipping. $\endgroup$ Commented May 23, 2020 at 15:09

2 Answers 2

0
$\begingroup$

I think I got it, but I might be wrong so be prepared.

There will be difference because of the way the carbons in the ring are hybridized. An sp2 hybridization state would make conformations impossible. An sp3 carbon allows both axial and equatorial positions for each group. So there would be no way to ensure that the bulky groups always interact.

$\endgroup$
0
$\begingroup$

The ortho effect is an effect that is closely linked with planarity. Only aromatic/anti-aromatic rings are planar and only the groups attached to aromatic rings can stabilise themselves through the resonance effect. However, in non-aromatic rings like cyclohexane, there is no planarity. The carbons are also sp3 hybridised. So the interaction between the bulky groups will not matter anyways.

$\endgroup$

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service and acknowledge you have read our privacy policy.

Not the answer you're looking for? Browse other questions tagged or ask your own question.