MWF_30 - Organic Lecture Series CH 310/318 M Textbook...

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Organic Lecture Series 1 CH 310/318 M LECTURE 30 Textbook Assignment: Chapter 9- Nucleophilic Substitution Today’s Topics: The Sn1 and Sn2 Reactions The Sn1 and Sn2 Reactions Notice & Announcements: Office Moved to WEL 4.242 Organic Lecture Series 2 Nucleophilic Nucleophilic Substitution Substitution and and β β - - Elimination Elimination Chapter 9 Chapter 9
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Organic Lecture Series 3 • For an S N 1 reaction at a chiral center, the R and S enantiomers are formed in equal amounts, and the product is a racemic mixture. C H Cl -Cl - C+ H CH 3 OH -H + 3 OC H CO C H 3 H R Enantiomer S Enantiomer + R Enantiomer A racemic mixture Planar carbocation (achiral) Stereochemistry Stereochemistry Organic Lecture Series 4 •Fo r S N 1 reactions at a chiral center – examples of complete racemization have been observed, but – partial racemization with a slight excess of inversion is more common. Approach of the nucleophile from this side is less hindered + R 1 C H R 2 - nucleophile from this side is partially blocked by leaving group, which remains associated with the carbocation as an ion pair Stereochemistry Stereochemistry
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Organic Lecture Series 5 1 2 Cl - Chloride ion can partially block this face of the ion pair When the two ions are close toeachother, they are called "contact ion pairs" 1 2 Cl - As solvent molecules interact to push the ions apart, they are called "solvent separated ion pairs" Organic Lecture Series 6 • For an S N 2 reaction at a chiral center, there is inversion of configuration at the chiral center.
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MWF_30 - Organic Lecture Series CH 310/318 M Textbook...

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