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Organic Chemistry Tips and Tricks
How (and why) electrons flow
Last updated: January 23rd, 2024 |
So what is the key “driving force” involved in chemistry? A chemist would say that “opposite charges attract, like charges repel.” But how can we make that concept more concrete and specific?
I’ve been going through Daniel Levy’s excellent book “Arrow Pushing in Organic Chemistry” (fuller review to come). The following excerpt nicely summarizes the driving force for electron flow (and therefore, chemical reactivity). Emphasis is from the author:
As a rule, electrons will flow from atomic centers high in electron density to atomic centers low in electron density. This dependence on polarity is similar to the way that electricity flows in an electric circuit. If there is no difference in electrical potential between the ends of a wire, electricity will not flow. If we imagine a simple hydrocarbon such as ethane, we can analogously relate this system to a nonpolarized wire. Both carbon atoms possess the same density of electrons and thus ethane has no polarity. However if functionality is added to ethane through introduction of groups bearing heteroatoms, the polarity changes and electron flow can be used to induce chemical reactions. These heteroatom bearing groups are known as functional groups and serve to donate or withdraw electron density.
While functional groups can be either electron donating or electron withdrawing, these properties rely upon the specific heteroatoms the functional group is composed of as well as the configuration of these heteroatoms relative to each other. With respect to the specific heteroatoms, electronegativity of the heteroatoms is the driving force influencing polarity. Thus the more electronegative the atom, the greater the affinity of electrons for this atom. As a calibration for electronegativity, the periodic table of the elements serves as an excellent resource. Specifically, moving from left to right and from bottom to top, electronegativity increases…
Dr. Levy’s book is an excellent guide to understanding the main types of reactions you’ll encounter in a typical organic chemistry course. You can buy it here.
00 General Chemistry Review
01 Bonding, Structure, and Resonance
02 Acid Base Reactions
03 Alkanes and Nomenclature
04 Conformations and Cycloalkanes
05 A Primer On Organic Reactions
06 Free Radical Reactions
07 Stereochemistry and Chirality
08 Substitution Reactions
09 Elimination Reactions
10 Rearrangements
11 SN1/SN2/E1/E2 Decision
12 Alkene Reactions
13 Alkyne Reactions
14 Alcohols, Epoxides and Ethers
15 Organometallics
16 Spectroscopy
17 Dienes and MO Theory
18 Aromaticity
19 Reactions of Aromatic Molecules
20 Aldehydes and Ketones
21 Carboxylic Acid Derivatives
22 Enols and Enolates
23 Amines
24 Carbohydrates
25 Fun and Miscellaneous
26 Organic Chemistry Tips and Tricks
- Common Mistakes: Formal Charges Can Mislead
- Partial Charges Give Clues About Electron Flow
- Draw The Ugly Version First
- Organic Chemistry Study Tips: Learn the Trends
- The 8 Types of Arrows In Organic Chemistry, Explained
- Top 10 Skills To Master Before An Organic Chemistry 2 Final
- Common Mistakes with Carbonyls: Carboxylic Acids... Are Acids!
- Planning Organic Synthesis With "Reaction Maps"
- Alkene Addition Pattern #1: The "Carbocation Pathway"
- Alkene Addition Pattern #2: The "Three-Membered Ring" Pathway
- Alkene Addition Pattern #3: The "Concerted" Pathway
- Number Your Carbons!
- The 4 Major Classes of Reactions in Org 1
- How (and why) electrons flow
- Grossman's Rule
- Three Exam Tips
- A 3-Step Method For Thinking Through Synthesis Problems
- Putting It Together
- Putting Diels-Alder Products in Perspective
- The Ups and Downs of Cyclohexanes
- The Most Annoying Exceptions in Org 1 (Part 1)
- The Most Annoying Exceptions in Org 1 (Part 2)
- The Marriage May Be Bad, But the Divorce Still Costs Money
- 9 Nomenclature Conventions To Know
- Nucleophile attacks Electrophile
This website answered all my questions that I keep on overthinking about. This is so much better than the textbooks! Thank you for this. The practice questions are so helpful too!
Glad you find it useful Francesca!
A Fantastic website. I was struggling with reaction mechanisms lately. I found this site as a recommendation on quora. I just visited it for a glance and absolutely fell in love with the website. You explain everything so clearly. Thank you for everything. Thank you for helping me learn OC
Thanks for everything. I’m working through the site and filling in all of the gaps in my understanding. One quick note: In the first sentence of your second quoted paragraph, it refers to “functional gorups”. I’m pretty sure this should be “functional groups”. Not sure if it’s a typo on your part or the author’s part, but it should probably be changed either way.
Fixed, thank you!
This website is brilliant. That’s exactly what I need to perfectly understand organic chemistry!
Thank you for this.
Happy you find the website useful, Michaela!
A common miss-conception we gleefully pass on to U/grads via VSEPR etc.. In the Heitler-London bonding theory, the main driving force is quantum mechanical electron delocalization. Electrostatic energy only accounts for about 20% of the BE.
Thank you for this.
Thank you very much. All content is so easy to grabe and concept clearing. I’m loving this site. Thanks for teaching us :)
Thank you for this resource are there any animations in the courses
Nice analogy to electrical conductivity! It’s also interesting to look at the periodic table as a map of chemical potential. Helps explain why, e.g., organolithiums are very “jazzed up” compounds; yet, in isolation, they just sit around. Putting an organolithium in the presence of water is the equivalent of hooking a load up to a 10 MW power source!