SN1/SN2/E1/E2: Don't Guess, *Know* Which Mechanism!
Chemistry in a Nutshell
107,151 views
What mechanism is going to happen? You'll know by the end of this video! A flow chart for deciding between SN1, SN2, E1, and E2 mechanisms is explained. The ultimate decision matrix for discerning which reaction pathway prevails under various conditions!
š„Download the FREE Flow Chart: Patreon: sn2-sn1-e2-e1-145286298
šMaster the Mechanisms! Grab the Organic Chemistry Reaction Mechanisms Survival Guide: https://payhip.com/b/rYbBp
š§ Full Mechanisms Playlist: Reaction Mechanisms in Organic Chemistry: ...
šµBuy the Professor a tea to keep the videos coming: Patreon: ChemistryinaNutshell
š§¬If you need a refresher on chirality for mechanisms to make sense, start here: Chirality & Stereochemistry Full Unit (R/S...
š§ŖFor all of my ochem videos in one place: Organic Chemistry: Full Video Library
š¦ If you need to take the MCAT: MCAT Chemistry Review: General & Organic C...
š„½As an Amazon Affiliate, I earn from qualifying purchases at no extra cost to you.
š„¼Need a molecular model kit or other chem supplies? https://www.amazon.com/shop/chemnut?c...
š¬Start any shopping journey here: https://amzn.to/3IXuAcS
0:00 The Big Question: SN1, SN2, E1, or E2?
0:39 SN1 and E1: The Carbo-cation Common Ground
1:20 Carbocation Stability (Tertiary vs. Secondary)
2:06 SN1: Nucleophilic Substitution Mechanism
2:33 E1: Beta-Elimination Mechanism
3:16 The Temperature Trick: Heat vs. Room Temp
3:45 SN2: The Famous Backside Attack & Inversion
5:23 E2: Strong Base Mechanism
6:34 E2 Conditions: Tertiary, Secondary, and Bulky Bases
7:42 The Ultimate Flow Chart (Actionable Steps)
7:56 Rule 1: Methyl Substrates (SN2 Only)
8:34 Rule 2: Primary Substrates (SN2 vs. Bulky Base E2)
9:38 Rule 3: Secondary Substrates (The 4-Way Split)
10:59 Rule 4: Tertiary Substrates (No SN2 Allowed!)
11:38 Practice Problems & Mechanism Identification
11:51 Problem A Walkthrough (Primary + Medium Base)
12:28 Problem B Walkthrough (Secondary + Strong Base)
13:20 Problem C Walkthrough (Tertiary + Weak Nucleophile)
14:10 Final Major Products Revealed
Citations:
Paula Yurkanis Bruice, "Organic Chemistry" 8th ed
https://openstax.org/details/books/or...
https://openstax.org/details/books/ch...
Music: Electron Clouds with a Chance of Swing
20 Comments
What a great job. Thank you for each droplet of quality in all your vids!
i am at uni studying bio, never learned anything about chemistry in school except maybe basic knowledge of the periodic table. so uni chemistry is A LOT for me! after barely passing inorganic chemistry, here i am losing my mind over OC. the thing is, i even like it! its just sooo much and i pretty much feel overwhelmed by the mass of information.
anyways, thanks a lot for this video as it helped me grasp some of the mess that lays before me! i am looking forward to watching more videos of your channel! its very much appreciated!
SN1/SN2/E1/E2: Don't Guess, *Know* Which Mechanism!
Chemistry in a Nutshell
107,151 views
What mechanism is going to happen? You'll know by the end of this video! A flow chart for deciding between SN1, SN2, E1, and E2 mechanisms is explained. The ultimate decision matrix for discerning which reaction pathway prevails under various conditions!
š„Download the FREE Flow Chart: Patreon: sn2-sn1-e2-e1-145286298
šMaster the Mechanisms! Grab the Organic Chemistry Reaction Mechanisms Survival Guide: https://payhip.com/b/rYbBp
š§ Full Mechanisms Playlist: Reaction Mechanisms in Organic Chemistry: ...
šµBuy the Professor a tea to keep the videos coming: Patreon: ChemistryinaNutshell
š§¬If you need a refresher on chirality for mechanisms to make sense, start here: Chirality & Stereochemistry Full Unit (R/S...
š§ŖFor all of my ochem videos in one place: Organic Chemistry: Full Video Library
š¦ If you need to take the MCAT: MCAT Chemistry Review: General & Organic C...
š„½As an Amazon Affiliate, I earn from qualifying purchases at no extra cost to you.
š„¼Need a molecular model kit or other chem supplies? https://www.amazon.com/shop/chemnut?c...
š¬Start any shopping journey here: https://amzn.to/3IXuAcS
0:00 The Big Question: SN1, SN2, E1, or E2?
0:39 SN1 and E1: The Carbo-cation Common Ground
1:20 Carbocation Stability (Tertiary vs. Secondary)
2:06 SN1: Nucleophilic Substitution Mechanism
2:33 E1: Beta-Elimination Mechanism
3:16 The Temperature Trick: Heat vs. Room Temp
3:45 SN2: The Famous Backside Attack & Inversion
5:23 E2: Strong Base Mechanism
6:34 E2 Conditions: Tertiary, Secondary, and Bulky Bases
7:42 The Ultimate Flow Chart (Actionable Steps)
7:56 Rule 1: Methyl Substrates (SN2 Only)
8:34 Rule 2: Primary Substrates (SN2 vs. Bulky Base E2)
9:38 Rule 3: Secondary Substrates (The 4-Way Split)
10:59 Rule 4: Tertiary Substrates (No SN2 Allowed!)
11:38 Practice Problems & Mechanism Identification
11:51 Problem A Walkthrough (Primary + Medium Base)
12:28 Problem B Walkthrough (Secondary + Strong Base)
13:20 Problem C Walkthrough (Tertiary + Weak Nucleophile)
14:10 Final Major Products Revealed
Citations:
Paula Yurkanis Bruice, "Organic Chemistry" 8th ed
https://openstax.org/details/books/or...
https://openstax.org/details/books/ch...
Music: Electron Clouds with a Chance of Swing
šMaster the Mechanisms! Grab the Organic Chemistry Reaction Mechanisms Survival Guide: https://payhip.com/b/rYbBp
š§ This video is part of my full mechanisms playlist: https://www.youtube.com/playlist?list=PLvUW25kBaMMtvqt_IBtezyBX_kk447pxZ
To viewers asking about solvents: I left them out on purpose! Most college exams use solvents that simply "confirm" the mechanism:
ā¢ SN1/E1 prefer polar protic (water, alcohols) to stabilize the carbocation.
ā¢ SN2/E2 prefer polar aprotic (DMSO, acetone, DMF) to boost nucleophile reactivity.
I didn't see "mismatched" solvents or heavy nuance until I was in a PhD-level class. For now, use the flowchart's core logic. It will get you the right answer >99.99% of the time!