Lecture 22 - chlorides react with R 2 CuLi Rxn. of...

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1 Reading for Wednesday ± Chapter 21: 21.1-21.6 ± We are skipping 21.4 ± Exams are ready for pickup ± Pickup Location: 4019 Malott (O-Chem Stockroom) ± You will need your KUID!!!! ± Note: Bruce is not there from 11am-noon!! ± Grades will be posted today Exam 2 No ARIS Quiz this Week! ± Quiz 5 will be available Wednesday March 30 Mon. 6:00-7:30 pm MAL 3092 Tues. 2:30-4:00 PM MAL 2007 Wed. 5:00-6:30 PM MAL 2001 Thurs. 9:30-10:50 AM MAL 1003 Sat. 11:30 AM-1:00 PM MAL 2007 PLUS Sessions THIS WEEK Chapter 20 Introduction to Carbonyl Chemistry Organometallic Reagents: Reaction with Aldehydes and Ketones (20.10) RMgX and RLi (including RC CLi) react with ketones and aldehydes to produce alcohols R 2 CuLi do not react Protic solvents must be avoided!
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2 Rxn. of Organometallic Reagents with Carboxylic Acid Derivs. (20.13) Esters and acid chlorides form 3º alcohols when reacted with 2 equiv. of RMgX or RLi A ketone is formed as an intermediate A ketone is the product when acid
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Unformatted text preview: chlorides react with R 2 CuLi Rxn. of Organometallic Reagents with Other Compounds (20.14) Grignard reagents react with CO 2 followed by H 3 O + to yield carboxylic acids RMgX, RLi and R 2 CuLi are all strong enough nucleophiles to open epoxides , -Unsaturated Carbonyl Compounds (20.15) Conjugated molecules Contain 2 electrophilic sites The carbonyl carbon The -carbon , -Unsaturated Carbonyl Compounds (20.15) RMgX and RLi attack at the carbonyl carbon (1,2-addition) Product is an allylic alcohol R 2 CuLi reagents attack at the -carbon (1,4-addition) Product is a ketone or aldehyde Synthesis (20.17) Ketones, aldehydes, alcohols (1, 2 or 3), alkenes, carboxylic acids and other classes of compounds can be obtained by synthetic sequences involving reactions with RMgX, RLi and R 2 CuLi...
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Lecture 22 - chlorides react with R 2 CuLi Rxn. of...

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