HMK 4.91

$sp, sp^{2}, sp^{3}, dsp^{3}, d^{2}sp^{3}$

Girija_3E
Posts: 27
Joined: Fri Sep 29, 2017 7:07 am
Been upvoted: 1 time

HMK 4.91

This problem asks to draw the Lewis structure of benzyne (C6H4) using two double bonds and a triple bond, which I did, but then asks us to explain why this molecule is highly reactive. Could someone please explain why it would be highly reactive? Thank you!

ConnorThomas2E
Posts: 57
Joined: Fri Sep 29, 2017 7:04 am

Re: HMK 4.91

I believe it is because the triple bond in Benzyne results in a linear shape for that carbon, which in turn makes it highly reactive because the molecule typically is not linear. The triple bond will break because of this and form a double bond with a more stable shape.

Sara Sasaki 1K
Posts: 48
Joined: Fri Sep 29, 2017 7:05 am

Re: HMK 4.91

I could be mistaken but I think it's the opposite actually: the two sp hybridized carbon atoms are in a more constrained position since it's in a six-figure chain (at 120 degree angle), instead of the arrangement it would normally have, which is linear (with a 180 degree angle). Therefore, it's more highly reactive in that formation.

Hope this helps!

Rachel Formaker 1E
Posts: 86
Joined: Fri Sep 29, 2017 7:04 am
Been upvoted: 2 times

Re: HMK 4.91

The solutions manual also states that because the triple bonded carbons are strained in the ring formation, they may form a diradical in which the triple bond is replaced by a double bond with a single radical electron on each carbon. This would also result in a very reactive molecule because of the radicals.