lecture 25 - Organic Lecture Series CH 310/318 M LECTURE 25...

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Organic Lecture Series 1 CH 310/318 M LECTURE 25 Textbook Assignment: Chapter 10- Alcohols Today’s Topics: Dehydration; oxidations Dehydration; oxidations Notice & Announcements: XM3 Grading in Progress Organic Lecture Series 2 Alcohols Alcohols Chapter 10 Chapter 10
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Organic Lecture Series 3 • Reaction of an alcohol with SOCl 2 in the presence of a 3° amine is stereoselective. – It occurs with inversion of configuration. OH SOCl 2 Cl SO 2 HCl + 3° amine + + ( S )-2-Octanol Thionyl chloride ( R )-2-Chlorooctane Reaction with SOCl Reaction with SOCl 2 N R R(H) SOCl 2 1 o &2 o ROH OH H R Cl H 1 o o Chloride Pyridine or N(Et) 3 Organic Lecture Series 4 • An alcohol can be converted to an alkene by acid-catalyzed dehydration (a type of β - elimination). – 1° alcohols must be heated at high temperature in the presence of an acid catalyst, such as H 2 SO 4 or H 3 PO 4 . 2° alcohols undergo dehydration at somewhat lower temperatures. – 3° alcohols often require temperatures at or only slightly above room temperature. Dehydration of ROH Dehydration of ROH
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Organic Lecture Series 5 180°C CH 3 2 OH H 2 SO 4 2 =CH 2 + H 2 O 140°C Cyclohexanol Cyclohexene H 2 O H 2 SO 4 3 COH 3 3 H 2 SO 4 3 C=CH 2 3 + H 2 O 50°C 2-Methyl-2-propanol ( tert- Butyl alcohol) 2-Methylpropene (Isobutylene) Dehydration of ROH Dehydration of ROH Ease of formation of C+ Organic Lecture Series 6 – Where isomeric alkenes are possible, the alkene having the greater number of substituents on the double bond (the more stable alkene) usually predominates (Zaitsev rule).
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This note was uploaded on 03/20/2011 for the course CHEMISTRY 310m taught by Professor Iverson during the Fall '08 term at University of Texas at Austin.

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lecture 25 - Organic Lecture Series CH 310/318 M LECTURE 25...

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