4.91 Benzyne

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Danah Albaaj 1I
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Joined: Fri Sep 29, 2017 7:07 am

4.91 Benzyne

Postby Danah Albaaj 1I » Sat Nov 18, 2017 2:49 pm

This problem asks me to draw a Lewis structure of benzyne (C6H4) including the hybridization of each carbon atom, then use my knowledge of bonding to explain why benzyne might be a reactive molecule. I know that the triple bond within the molecule would play a significant role, I'm just not exactly sure as to how/why. Could someone please elaborate on this for me?

Lianna Kishi 1A
Posts: 23
Joined: Thu Jul 27, 2017 3:00 am

Re: 4.91 Benzyne

Postby Lianna Kishi 1A » Sat Nov 18, 2017 9:42 pm

The carbons that are triple bonded to each other are sp hybridized. While their hybridization would normally like to adopt a linear arrangement with 180 degree angles, the angles are closer to 120 because they're in the ring. Because of this, benzyne has a very strained structure and is highly reactive.

Remi Lathrop 1G
Posts: 51
Joined: Fri Sep 29, 2017 7:07 am

Re: 4.91 Benzyne

Postby Remi Lathrop 1G » Sat Nov 18, 2017 9:48 pm

As mentioned in the comment above, the reason this molecule is highly reactive because the triple bond between the 2 carbons not attached to hydrogens are being forced into a shape that their sp hybridization would not normally produce. Because they are in a ring with all the other carbons, which are sp2 hybridized, the triple bond between the two carbons has bond angles closer to 120, even though under normal circumstances their bond angles would be 180.

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