Comments on: Nucleophilic Aromatic Substitution (2) – The Benzyne Mechanism

By: Xaid

Xaid — Tue, 14 Apr 2026 20:13:23 +0000

I have a little problem with the fact that electron delocalization via resonance is irrelevant . I feel like it should have a significant impact . Even though the negative charge on the carbon after nucleophilic attack cant be stabilized through conjugation , the electron density at ortha and para positions for electron withdrawing groups should be less than that without them. This reasoning stems from the electrophilic substitution reactions. So why doesnt this have any effect

By: James Ashenhurst

James Ashenhurst — Fri, 20 Mar 2026 00:56:46 +0000

In reply to Rishad. There is no strong preference. A mixture is obtained. If your instructor says ortho is favored exclusively over meta I would love to hear why, because that's not what's observed.

By: Rishad

Rishad — Thu, 19 Mar 2026 16:21:30 +0000

In that text of benzyne mechanism given that nucleophilic attack on o chloro toulene forms meta and ortho products both without favoring anyone of them.
Pls confirm what should be major as in my exam ortho was given pls clarify!

By: Shweta

Shweta — Wed, 05 Mar 2025 07:11:07 +0000

This is a very informative post! However there’s a doubt with CF3 substituent. Cf3 shows negative hyperconjugation which doesn’t act at meta positions(only at ortho and para)..So shouldn’t that stabilize the anion/negative charge at para position more as opposed to at meta position. Shouldn’t -Nh2 then be attached to meta position in the major product and not to para position then..?

By: Hina

Hina — Sat, 13 Jan 2024 07:33:43 +0000

How protic and aprotic solvent effect benzyne formation. (Brief explanation needed)

By: James Ashenhurst

James Ashenhurst — Sun, 30 Apr 2023 23:49:32 +0000

In reply to RUPANKITA MUKHERJEE. Thank you

By: RUPANKITA MUKHERJEE

RUPANKITA MUKHERJEE — Sun, 30 Apr 2023 15:26:00 +0000

So wellexplained and helpful! Your clear and lucid language really helps me a lot in understanding many important topics. Whenever I look for doubt clearance with respect to organic chemistry and I find your post, I know they're gonna be well looked after. With tons of thanks, from India.

By: Amen Bibi

Amen Bibi — Sat, 11 Mar 2023 08:28:33 +0000

Thankyou so much. All content in this website is very informative

By: Ashif Hussain

Ashif Hussain — Wed, 08 Mar 2023 15:54:35 +0000

Thank you sir.It helps me to understand this concept which is very important for indian competitive exams.

By: Shweta

Shweta — Tue, 29 Nov 2022 12:28:30 +0000

Excellent ..the way you divided & explained the concept