310-7 - CH 310 N T Th 2-3:30 LECTURE 7 Textbook Assignment:...

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CH 310 N T Th 2-3:30 LECTURE 7 Textbook Assignment: Chapter 15 Begin Homework (for credit): POW 3 posted Today’s Topics: Organometallic Reagents-Begin Aldehydes & Ketones Notice & Announcements: Exam I: Monday 9/21 7-9 PM Last Name A-L: WEL 1.308 Last Name M-Z: WEL 2.224
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Organic Lecture Series 2 Organometallic Organometallic Reagents Reagents
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Organic Lecture Series 3 A Simple Example: H 3 C CH 3 O 3 2 2 H 3 C 3 O 3 2 2 alkoxide MgBr H OH H 3 C 3 O H 3 2 2 alcohol MgBrOH H 2 O Mg(OH) 2
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Organic Lecture Series 4 • Lithium diorganocopper reagents, known more commonly as Gilman reagents Gilman reagents – prepared by treating an alkyl, aryl, or alkenyl lithium compound with Cu(I) iodide 2CH 3 CH 2 2 2 Li + CuI or THF diethyl ether (CH 3 2 2 2 ) 2 Cu - Li + + LiI Butyllithium Copper(I) iodide Lithium dibutylcopper (a Gilman reagent) Gilman Reagents Gilman Reagents
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Organic Lecture Series 5 • Coupling within organohalogen compounds – form new carbon-carbon bonds by coupling with alkyl and alkenyl chlorides, bromides, and iodides Example Example I 1. Li, pentane 2. CuI CuLi Br 2-Methyl-1-dodecene 1-Iododecane or THF diethyl ether 2 R'Br R 2 CuLiBr R'-R RCu LiBr or THF + ++ Reactions Reactions
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Organic Lecture Series 6 I CuLi 2 diethyl ether + or THF Lithiu m dibutylcopper trans- 1-Iodo-1-nonene 5-Tridecene coupling with a vinylic halide is stereospecific: the configuration of the carbon-carbon double bond is retained Reactions Reactions
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This note was uploaded on 10/31/2009 for the course CH 310n taught by Professor Iverson during the Spring '08 term at University of Texas.

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310-7 - CH 310 N T Th 2-3:30 LECTURE 7 Textbook Assignment:...

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