Comments on: Hidden Hydrogens, Hidden Lone Pairs, Hidden Counterions

By: The Most Important Question To Ask When Learning a New Reaction | Straight A Mindset

Thu, 07 Dec 2023 22:16:46 +0000

[…] or two of Org 1 is devoted to just that topic. In this case you’ll need to know about all the atoms that are hidden in these line […]

By: How To Determine Hybridization: A Shortcut | Straight A Mindset

How To Determine Hybridization: A Shortcut | Straight A Mindset — Tue, 17 Oct 2023 23:25:08 +0000

[…] arrows point to (A, B, C, D, E). A and B especially. If you haven’t mastered line diagrams yet (and “hidden” hydrogens) maybe get some more practice and come back to this […]

By: Alen

Alen — Mon, 26 Sep 2016 11:51:47 +0000

Hi James,

I really like your site, it is very informative. However, I didnt notice any topics on hydrogen bonding and I was wondering if you could try answering my somewhat peculiar question. Is it possible to get a hydrogen bonding between a hydroxy (R-OH) group and alkoxide (R-O-) group if pKa values of both are somewhat similar or if they differ greatly? or do we get a simple proton transfer reaction?

To be more specific, I have a material which has alkoxide functionality on the surface and I am wondering if an alcohol (phenol) could form a stronger H-bond in comparison to the material with hydroxyl functionality?

Cheers

By: Robert Grossman

Robert Grossman — Thu, 06 Aug 2015 19:54:19 +0000

Thanks for the kind words. The resonance structure rule is Meier’s rule, named after my colleague Mark Meier, who says, “When in doubt, draw in all the lone pairs, and then draw resonance structures until the cows come home.” The “cows come home” part is very important.

By: Grossman’s Rule

Grossman’s Rule — Thu, 06 Oct 2011 08:31:45 +0000

[…] few months ago after putting up this post on “Hidden Hydrogens, Hidden Lone Pairs, and Hidden Counterions”, commenter Stewie Griffin made me aware of this little gem: With regards to hidden hydrogens, […]

By: Chemjobber

Chemjobber — Wed, 28 Sep 2011 12:57:51 +0000

4th! on Grossman’s rule. A very useful thought, early in the book.

[I bumped into him at NOS 2003 literally. I excused myself, looked at his name tag and said, “I have your book — it’s great!” He’s terribly modest.]

By: azmanam

azmanam — Wed, 29 Jun 2011 16:25:24 +0000

3rd for Grossman’s rule and the resonance rule in his book (I don’t know if he attributes it to himself or someone else):

The 2nd best resonance structure usually defines a molecules reactivity.
-It explains Markovnikov’s rule, Electrophilic Aromatic Substitution, enolate chemistry…

By: James

James — Wed, 29 Jun 2011 02:23:11 +0000

In reply to Texascarbon. since 2 people have mentioned it I'll have to do a post on Grossman's rule. thanks for the input.

By: Texascarbon

Texascarbon — Tue, 28 Jun 2011 23:49:03 +0000

Grossmans rule is super useful. It also helps prevent that accidental dropping of carbons. Whenever I tutor I always encourage addingin everything to help avoiding mistakes.

By: James

James — Tue, 28 Jun 2011 20:42:55 +0000

In reply to Stewie Griffin. that *is* effective, thanks for bringing it to my attention. I have the Grossman book but don't recall the rule. Thanks!