318-9 - CH 318 N LECTURE 9 Textbook Assignment: Chapter 15...

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CH 318 N LECTURE 9 Textbook Assignment: Chapter 15 Homework (for credit): POW 4 posted Today’s Topics: Organometallic Reagents Notice & Announcements: Organic Lecture Series 2 Organometallic Organometallic Compounds Compounds
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Organic Lecture Series 3 Organometallic Compounds • Organometallic compound: Organometallic 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 Organic Lecture Series 4 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 Mg + 1-Bromobutane Butylmagnesium bromide (an alkyl Grignard reagent) ether Br MgBr + ether Mg Br MgBr Bromobenzene Phenylmagnesium bromide (an aryl Grignard reagent)
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Organic Lecture Series 5 RMgX and RLi • Grignard reagents dissolve as coordination compounds solvated by ether – ethylmagnesium bromide, EtMgBr Organic Lecture Series 6 RMgX and RLi • Organolithium reagents – prepared by reaction of an alkyl, aryl, or alkenyl halide with lithium metal Cl + + 1-Chlorobutane Butyllithium pentane 2Li LiCl Li
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Organic Lecture Series 7 RMgX and RLi The carbon-metal bonds in RMgX and RLi are polar covalent 2.5 - 1.2 = 1.3 2.5 - 1.0 = 1.5 2.5 - 1.5 = 1.0 2.5 - 1.6 = 0.9 2.5 - 1.8 = 0.7 2.5 - 1.9 = 0.6 Difference in Electronegativity C-M Bond Percent Ionic character* 60 52 40 36 28 24 C-Li C-Mg C-Al C-Zn C-Sn C-Hg *Percent ionic character = E C -E M E C x 100 2.5 - 1.9 = 0.6 24 C-Cu Increasing Ionic Character Organic Lecture Series 8
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This note was uploaded on 04/20/2009 for the course CH 318N taught by Professor Willson during the Spring '08 term at University of Texas at Austin.

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318-9 - CH 318 N LECTURE 9 Textbook Assignment: Chapter 15...

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