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Chemistry LibreTexts

Benzyne

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Hydrocarbon 1 is called benzyne.

benzyne1.png

Derivatives of 1 are called benzynes or arynes.

eg:

benzyne2.png

If each triply bonded carbon atom in a benzyne molecule is sp-hybridized, as is typical of triply bonded carbon atoms, there would be severe angle strain in the molecule. It is more likely that each triply bonded carbon atom in a benzyne molecule is sp2-hybridized, in which case two sp2-hybridized orbitals that are not parallel to each other overlap laterally to form the pi bond that is not part of the loop of pi electrons (2).

benzyne3.png

In either case, the pi bond in a benzyne molecule that is not part of the loop of pi electrons would be very weak, which is consistent with the observation that, despite being aromatic, benzynes are extremely unstable and reactive. If generated in isolation, benzynes undergo rapid dimerization.

eg:

benzyne4.png

Mechanism

Step 1:

benzyne5.png

Step 2:

benzyne6.png

see also benzyne mechanism

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This page titled Benzyne is shared under a All Rights Reserved (used with permission) license and was authored, remixed, and/or curated by Gamini Gunawardena via source content that was edited to the style and standards of the LibreTexts platform.

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