7.2 SN1 Reactions | Organic Chemistry

Chad comprehensively covers SN1 reactions beginning with the SN1 reaction mechanism and the SN1 rate law. He shows how the leaving group leaves forming a carbocation in the slow step, and how the substrate is the only reactant in the rate law as SN1 reactions are 1st order. He then explains SN1 reaction stereochemistry, how and why racemization occurs in SN1 reactions when a chiral center is formed, and how the SN1 reaction reactivity order for substrates is from most substituted to least substituted as more substituted carbocations are stable intermediates and form faster in the slow step.

Chad then shows the energy diagram for a typical SN1 reaction and explains how most SN1 reactions involve a weak nucleophile. He then explains how carbocation rearrangements are possible in SN1 reactions, how to predict when they should occur, and the arrow-pushing needed to represent the carbocation rearrangement in the mechanism including for both hydride shifts and alkyl shifts. Finally, Chad concludes the lesson by showing that a polar protic solvent is required in SN1 reactions to stabilize the carbocation intermediate, and that a good leaving group (Cl, Br, I, OTs) is also required.

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00:00 Lesson Introduction
00:53 SN1 Reaction Mechanism and SN1 Rate Law
06:30 SN1 Reaction Stereochemistry - Racemization
09:24 Substrate Effects in SN1 Reactions
11:44 Energy Diagrams for SN1 Reactions
14:45 Nucleophile Effects in SN1 Reactions
16:16 Carbocation Rearrangements in SN1 Reactions
21:38 Polar Protic Solvents in SN1 Reactions
23:37 Good Leaving Groups in SN1 Reactions

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