lecture 4 - Organic Lecture Series CH 310 N LECTURE 5...

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Organic Lecture Series 1 CH 310 N LECTURE 5 Textbook Assignment: Chapter 15 Organometallic Reagents Homework (for credit): Problem set 1 posted Today’s Topics: Basics of organometallic reagents Notice & Announcements: Organic Lecture Series 2 Organometallic Organometallic Compounds Compounds (Chapter 15) (Chapter 15)
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Organic Lecture Series 3 • Organometallic Organometallic compound: compound: a compound that contains a carbon-metal bond • The focus will be on organometallic compounds of Mg, Li, and Cu – these classes illustrate the usefulness of organometallics in modern synthetic organic chemistry – the use of organometallics can bring about transformations that cannot be accomplished in any other way Organometallic Organometallic compound compound Organic Lecture Series 4 Organometallic reagents have 2 general types of reactions: 1. As Strong bases (Bronsted-Lowry) 2. As nucleophilic reagents. Regard the alkyl group as “R -
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Organic Lecture Series 5 Grignard Reagents Grignard Reagents • Grignard reagent: Grignard reagent: an organomagnesium compound – prepared by addition of an alkyl, aryl, or alkenyl (vinylic) halide to Mg metal in diethyl ether or THF Organic Lecture Series 6 Mg + 1-Bromobutane Butylmagnesium bromide (an alkyl Grignard reagent) ether Br MgBr + ether Mg Br MgBr Bromobenzene Phenylmagnesium bromide (an aryl Grignard reagent) Examples:
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Organic Lecture Series 7 • Grignard reagents dissolve as coordination compounds solvated by ether – ethylmagnesium bromide, EtMgBr Organic Lecture Series 8 Organolithium reagents – prepared by reaction of an alkyl, aryl, or alkenyl halide with lithium metal Cl + + 1-Chlorobutane Butyllithium pentane 2Li LiCl Li Organolithium Organolithium reagents reagents
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Organic Lecture Series 9
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lecture 4 - Organic Lecture Series CH 310 N LECTURE 5...

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