Uploaded November 2025 | Updated September 2026, 2 weeks ago
We cover the complete reaction mechanism for E2 (biomolecular elimination) in organic chemistry: mechanism, Zaitsev's Rule for determining major products, when Zaitsev's Rule FAILS (Hofmann Elimination), and tricky cases like cyclic structures and choosing the major product between a pair of cis/trans isomers. (Zaitsev's Rule is also called Zaytsev's Rule, Saytzeff's Rule, or Saytzev's Rule.)
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0:00 Bimolecular Elimination Reactions
0:25 E2 Overall Equation
1:45 E2 Generic Pattern
4:29 Symmetrical (Easier) Example
6:42 Zaitsev's Rule Example
9:53 Hofmann Elimination (4 Exceptions to Zaitsev's Rule)
10:16 1 Conjugated Double Bond Systems
11:35 2 Bulky Bases
12:17 3 Leaving Group is too Basic
13:31 Fluorides...
13:54 4 Anti- & Syn-
16:42 Cyclic Systems
20:51 cis- vs trans- Major & Minor Products
21:31 Newman Projection Leading to Major Product
22:28 Newman Projection Leading to Minor Product
22:58 Why these lead to major vs minor
24:23 Newman Projections You Can Ignore
25:26 & when you can't ignore
Citations:
Paula Yurkanis Bruice, "Organic Chemistry" 8th ed
Chapter 9, base reactivity data from table 9.5
openstax.org/details/books/organic-chemistry
openstax.org/details/books/chemistry-2e
Music: youtu.be/lL6AsbG07xY
We cover the complete reaction mechanism for E2 (biomolecular elimination) in organic chemistry: mechanism, Zaitsev's Rule for determining major products, when Zaitsev's Rule FAILS (Hofmann Elimination), and tricky cases like cyclic structures and choosing the major product between a pair of cis/trans isomers. (Zaitsev's Rule is also called Zaytsev's Rule, Saytzeff's Rule, or Saytzev's Rule.)
📘Master the Mechanisms! Grab the Organic Chemistry Reaction Mechanisms Survival Guide: payhip.com/b/rYbBp
🧠Full Mechanisms Playlist: youtube.com/playlist?list=PLvUW25kBaMMtvqt_IBtezyBX_kk447pxZ
🍵Buy the Professor a tea to keep the videos coming: patreon.com/c/ChemistryinaNutshell
🧬If you need a refresher on chirality for mechanisms to make sense, start here: youtube.com/playlist?list=PLvUW25kBaMMupOdw1Wgy8YauiQ40J_5nx
⚗️For all of my ochem videos in one place: youtube.com/playlist?list=PLvUW25kBaMMuKRkW9gDV7vlAk4Y9WRU7c
🥼If you need to take the MCAT: youtube.com/playlist?list=PLvUW25kBaMMuJZI5IVWO8X0syBANn-YqY
🥽As an Amazon Affiliate, I earn from qualifying purchases at no extra cost to you.
🥼Need a molecular model kit or other chem supplies? amazon.com/shop/chemnut?ccs_id=11f20bce-5f74-427b-85fb-bdf66849405a
🔬Start any shopping journey here: amzn.to/3IXuAcS
0:00 Bimolecular Elimination Reactions
0:25 E2 Overall Equation
1:45 E2 Generic Pattern
4:29 Symmetrical (Easier) Example
6:42 Zaitsev's Rule Example
9:53 Hofmann Elimination (4 Exceptions to Zaitsev's Rule)
10:16 1 Conjugated Double Bond Systems
11:35 2 Bulky Bases
12:17 3 Leaving Group is too Basic
13:31 Fluorides...
13:54 4 Anti- & Syn-
16:42 Cyclic Systems
20:51 cis- vs trans- Major & Minor Products
21:31 Newman Projection Leading to Major Product
22:28 Newman Projection Leading to Minor Product
22:58 Why these lead to major vs minor
24:23 Newman Projections You Can Ignore
25:26 & when you can't ignore
Citations:
Paula Yurkanis Bruice, "Organic Chemistry" 8th ed
Chapter 9, base reactivity data from table 9.5
openstax.org/details/books/organic-chemistry
openstax.org/details/books/chemistry-2e
Music: youtu.be/lL6AsbG07xY





![SN2 Trap: Why (R) Doesnt Always Invert to (S)
Think SN2 always inverts R/S configuration? Dont fall for the (R) to (R) trap on your midterm! If youve been taught the Golden Rule that SN2 must flip between R/S, this video is required viewing.
Were dissecting a textbook lie utilizing a 1970s breakthrough from the H.C. Brown lab. Ill show you exactly how an (R) reactant can produce an (R) product through a perfectly standard SN2 mechanism, WITHOUT breaking a single rule.
📘Master the Mechanisms! Grab the Organic Chemistry Reaction Mechanisms Survival Guide: https://payhip.com/b/rYbBp
🧠Full Mechanisms Playlist: https://www.youtube.com/playlist?list=PLvUW25kBaMMtvqt_IBtezyBX_kk447pxZ
🍵Buy the Professor a tea to keep the videos coming: https://www.patreon.com/c/ChemistryinaNutshell
🧬If you need a refresher on chirality for mechanisms to make sense, start here: https://www.youtube.com/playlist?list=PLvUW25kBaMMupOdw1Wgy8YauiQ40J_5nx
⚗️For all of my ochem videos in one place: https://www.youtube.com/playlist?list=PLvUW25kBaMMuKRkW9gDV7vlAk4Y9WRU7c
🥼If you need to take the MCAT: https://www.youtube.com/playlist?list=PLvUW25kBaMMuJZI5IVWO8X0syBANn-YqY
What youll master in this gotcha question breakdown:
• The CIP Trap: Why (R) to (R) isnt a mechanism failure, but a priority change.
• Super-Hydride Logic: Dissection lithium triethylborohydride (LiEt3BH) to see why its the surgical strike of nucleophiles.
• The Spatial Literacy Test: Using 3D molecular models to see the backside attack when the 2D drawings fail you.
0:00 The 5-Point SN2 Chirality Trap
0:23 Tiebreakers: Assigning Priorities to the Reactant
1:00 The Hand Rule: Confirming the (R) Configuration
1:26 Is Super-Hydride too bulky for SN2?
1:48 [SOURCE] Krishnamurthy & Brown Paper (1982)
2:08 3D Model Walkthrough: Geometry of the Nucleophile
2:54 The Mechanism: Concerted Backside Attack
3:55 The Umbrella Inversion vs. Configuration
4:30 Re-evaluating Priorities for the Product
4:56 The Hand Rule: Why the Product is (R)
5:10 The Verdict: Why (R) stayed (R)
5:23 Pro-Tip: How to assign R/S in seconds
📖The Research (Primary Source for LiEt3BH): Selective reductions. 31. Lithium triethylborohydride as an exceptionally powerful nucleophile. A new and remarkably rapid methodology for the hydrogenolysis of alkyl halides under mild conditions
S. Krishnamurthy and Herbert C. Brown
The Journal of Organic Chemistry 1983 48 (18), 3085-3091
DOI: 10.1021/jo00166a031
https://pubs.acs.org/doi/pdf/10.1021/jo00166a031
🥽As an Amazon Affiliate, I earn from qualifying purchases at no extra cost to you.
🥼My recommendations: https://www.amazon.com/shop/chemnut?ccs_id=11f20bce-5f74-427b-85fb-bdf66849405a
🔬Start any shopping journey here: https://amzn.to/3IXuAcS
Citations:
Paula Yurkanis Bruice, Organic Chemistry 8th ed
https://openstax.org/details/books/organic-chemistry
https://openstax.org/details/books/chemistry-2e
Music: https://youtu.be/lL6AsbG07xY SN2 Trap: Why (R) Doesnt Always Invert to (S)](https://i.ytimg.com/vi/IHSRGx_GlZA/mqdefault.jpg)




