6 - 9/14/2011 Why do ketones react faster with strong bases...

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Unformatted text preview: 9/14/2011 Why do ketones react faster with strong bases than esters? Which C=O group is more stabilized by resonance? very fast ketone A strong base ester B fast Why do ketones react faster with strong bases than esters? ester Is there an analogous resonance stabilization of the product? A. yes B. no fast very fast ketone A B energy ∆E‡ reaction reaction Which C=O group is more stable? Does Does the greater stability of the ester C=O group make it A. more or B. less reactive? A ∆E‡ energy B reaction reaction 1 9/14/2011 What functional group is not present in rapamycin? A. amine B. ether C. ester general synthesis of esters D. amide E. ketone acid chloride alcohol ester Will rapamycin undergo the above reaction? A. yes B. no What is the major product of the following reaction? rapamycin What functional group is the product of this reaction? acid chloride A. amine alcohol B. ether C. ester ester D. amide E. ketone general synthesis of esters acid chloride alcohol Can these general organic reactions be understood? What is the product of the following reaction? ester O Li C C A What is the major product of the following reaction? O C + Li C ? B A B C D 12 2 9/14/2011 Is Is there more than one way to write curved arrows? How are organo halides compounds prepared? What happens when the product of this reaction is treated with lots of water? organo bromine H O C H H O C Br + H Br─C H Br Br O C C H Li Li O C + Li C C H O O + Li C C H O H C O C C + Li Br Why is this an important synthetic reaction? alkane Li OH How are carbonyl compounds prepared? alcohol carbonyls O=C C ─C + C─OH H Br Br O C C H Li Li O O C + Li C Li H C H O H C OH O C C C HPy CrO3 C + Li H + C C H O C H O C C + + Li Br Li OH How are organo metallic compounds prepared? H O O Li OH Carbon-carbon bond forming reactions are very important for converting simple organic compounds into complex organic compounds! organolithium organolithium Li─C Br C Li Li C H O O + Li C C H C O H H O O C C + + Li C O H O C C + Li Br C H Li OH 3 9/14/2011 Functional Groups and Organic Synthesis. Other reactions. hydrocarbon C ─C ll HH H2 C C C C H Pd/C H 19 22 Functional Groups and Organic Synthesis. Other reactions. alkenes C ═C H C OH C C C + H2O + Br Br hydrocarbon hydrocarbon C ─C ll HH H2 C C C C H Pd/C H 20 Functional Groups and Organic Synthesis alkenes H C OH C Br alkanes C C C OH haloalkanes C OH alcohols C Li organolithium H C C Br C H Pd/C aldehydes ketones C C H2 H PCC H Br 1. C O 2. H2O Li C C O Br C C C Li OH 21 4 ...
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