C341F2011Chapter7NS

Whichstepistherdsandwhy page 8 of 24 whatistheratelaw

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Unformatted text preview: a. Br Br Br Br Br b. Br Br Page 7 of 24 C341/Fall 2011 Chapter 7: Nucleophilic Substitution Reactions The SN1 Reaction This is a two‐step reaction mechanism. Which step is the RDS and WHY? Page 8 of 24 What is the rate law? C341/Fall 2011 Chapter 7: Nucleophilic Substitution Reactions SN1 Reactions & Substrate Reactivity Page 9 of 24 C341/Fall 2011 Chapter 7: Nucleophilic Substitution Reactions SN1 Reactions & Stereochemistry What accounts for the 35%/65% product ratio? Cl OH NaOH OH + 35% Page 10 of 24 65% C341/Fall 2011 Chapter 7: Nucleophilic Substitution Reactions SN1 vs. SN2 Overview Summary of considerations to make: • Will proton transfers be necessary? – Look at the quality of the leaving group. – Look at the stability of the final product. • Will the mechanism be SN1 or SN2? – Look at how crowded the electrophilic site is . – Look at how stable the resulting carbocation would be. • Are rearrangements likely? – Look for ways to improve the stability of the carbocation. • Will the product have inversion or racemization? – SN1=racemization while SN2=inversion. Page 11 of 24 C341/Fall 2011 Chapter 7: Nucleophilic Substitution Reactions 1. Predict the reagents nece...
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