Addition-Elimination Substitution on Aromatic Chloride Facilitated by a para-nitro group

Sn2

Click the structures and reaction arrows in sequence to view the 3D models and animations respectively

The hydroxide anion attacks para to the nitro group. The negative charge is delocalised around the ring to the nitro group which helps stabilise the transition state. The chloride anion is then eliminated.

Related Halex reaction and alternative benzyne intermediate mechanism.

See the effect of two nitro groups

M. Mąkosza, Russ. Chem. Bull., 1996, 45, 491–504.

516

()

How useful was this page?

Click on a star to rate it!

Average rating / 5. Vote count:

No votes so far! Be the first to rate this page.

As you found this page useful...

Follow us on social media!

We are sorry that this page was not useful for you!

Let us improve this page!

Tell us how we can improve this page (in your own language if you prefer)? If you would like a response, please include your email address e.g. [email protected]

Provided by the