Comments on: Disubstituted Benzenes: The Strongest Electron-Donor “Wins”

By: Hassan Riyaznur alom

Hassan Riyaznur alom — Thu, 05 Sep 2024 18:17:31 +0000

Today was my reaction mechanisms exam. And thankfully I go through your article. Ohh I can’t express my happiness. Just thank you.

By: James Ashenhurst

James Ashenhurst — Tue, 16 Jan 2024 09:17:14 +0000

In reply to tej gandhi. Thank you. I am so glad you are finding it helpful! James

By: tej gandhi

tej gandhi — Sat, 13 Jan 2024 14:54:22 +0000

i cant describe how wonderful this site is. its helped me understand and fall in love with organic chemistry

By: lea

lea — Wed, 15 Nov 2023 14:31:21 +0000

Hello again! I’m unable to reply to my previous comment (regarding catechol). I’ve understood now that out of the four of the possible products there are only two different ones. Thank you!. I have one more question, if there is a CHO group attached to catechol at position C-3 relative to one of the OH groups, what would be the product formed in the reaction with excess aqueous bromine. According to the markscheme there would be 2 bromines each at position adjacent to the 2 OH groups, if possible could you explain why? (Apologies if my questions sounds confusing it’s much easier to draw the structure)

By: James Ashenhurst

James Ashenhurst — Wed, 15 Nov 2023 14:11:12 +0000

In reply to lea.

Try this exercise. Draw out catechol (ortho-dihydroxybenzene). Label the two hydroxyl groups A and B. Now draw 4 products.
#1: Bromine is ortho to A
#2: bromine is para to A
#3: bromine is ortho to B
#4: bromine is para to B.

Now compare the four. Are they four different products?

By: lea

lea — Wed, 15 Nov 2023 10:50:48 +0000

This webpage has been really helpful! Thank you. However I still have a doubt. If two OH groups are attached to a benzene ring adjacent to each other and this is reacted with aqueous bromine, what will the major product be? In this case the two groups (OH) are the same and so where will they direct the incoming group? I’ve read somewhere that in this case we have to consider the symmetry of the molecule, however I’m still very confused about this.

By: James Ashenhurst

James Ashenhurst — Tue, 17 Jan 2023 11:48:36 +0000

In reply to Shreyansh Sharma. Thank you for the kind comment.

By: James Ashenhurst

James Ashenhurst — Tue, 17 Jan 2023 11:48:22 +0000

In reply to Shreyansh Sharma. Glad you found it useful and thanks for stopping by!

By: Alexandre Leroy

Alexandre Leroy — Sun, 15 Jan 2023 18:42:51 +0000

I got perfectly what I wanted in two minutes. Thanks.

By: James Ashenhurst

James Ashenhurst — Thu, 04 Aug 2022 15:46:51 +0000

In reply to Jacqueline.

I believe it would be ortho to the nitrile group because nitrile is less deactivating than NO2 according to this paper. https://pubs.acs.org/doi/pdf/10.1021/ja00775a028