318-9 - 1 CH 318 N T Th 8 9:30 LECTURE 9 Textbook...

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Unformatted text preview: 1 CH 318 N T Th 8 9:30 LECTURE 9 Textbook Assignment: Chapter 15 Homework (for credit): POW 4 posted Todays Topics: Organometallics Notice & Announcements: EXAM 1 Grading in Progress Organic Lecture Series Organic Lecture Series Organic Lecture Series Organic Lecture Series 2 Organometallic Organometallic Compounds Compounds Organic Lecture Series Organic Lecture Series Organic Lecture Series 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 2 Organic Lecture Series Organic Lecture Series Organic Lecture Series 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) Organic Lecture Series Organic Lecture Series Organic Lecture Series Organic Lecture Series 5 RMgX and RLi Grignard reagents dissolve as coordination compounds solvated by ether ethylmagnesium bromide, EtMgBr Organic Lecture Series Organic Lecture Series Organic Lecture Series 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 3 Organic Lecture Series Organic Lecture Series Organic Lecture Series 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 =...
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318-9 - 1 CH 318 N T Th 8 9:30 LECTURE 9 Textbook...

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