7.3 SN1 vs SN2 | Organic Chemistry

Chad compares and contrasts SN1 and SN2 reactions in this lesson. Chad begins by explaining that vinyl and aryl halides (sp2 halides) are not reactive in both SN1 and SN2 reactions. He then summarizes the differences between the two regarding the substrate, nucleophile, solvent, and the similarity in the leaving group trend.

Chad also reminds the student that rearrangements are only possible in SN1 reactions and that while inversion occurs in SN2 reactions, racemization occurs in SN1 reactions. Chad then proceeds to work 7 examples showing how to determine which mechanism, SN1 or SN2, is more likely and then how to predict the product(s) of the substitution reaction. Chad even includes an example of an SN1 reaction involving a carbocation rearrangement and one involving a resonance-stabilized carbonation.

If you want all my study guides, quizzes, and practice exams, check out my premium course at https://www.chadsprep.com/organic-che...

00:00 Lesson Introduction
00:56 Vinyl and Aryl Halides are Unreactive
02:24 SN1 vs SN2: Substrate, Nucleophile, Solvent, and Leaving Group Trends
05:20 SN1 vs SN2 Example #1 - Strong Nucleophile
07:16 SN1 vs SN2 Example #2 - Tertiary Substrate
09:21 SN1 vs SN2 Example #3 - Weak Nucleophile
11:52 SN1 vs SN2 Example #4 - Strong Nucleophile with Inversion
13:19 SN1 vs SN2 Example #5 - SN1 with Rearrangement
15:58 SN1 vs SN2 Example #6 - Substitution with Allylic Substrate
18:59 SN1 vs SN2 Example #7 - Strong, Neutral Nucleophile

https://www.chadsprep.com/