Chapter 18_Class Notes - Chapter 18 Ethers Epoxides Thiols...

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Chapter 18: Ethers, Epoxides, Thiols and Sulfides Outline Slides 2-5_Chapter 18_Classification_IUPAC and Properties of Ethers_ Youtube Video 1 Slides 6-8_Chapter 18_Preparation of Ethers_ Youtube Video 2 Slides 9-13_Chapter 18_Reactions of Ethers_ Youtube Video 3 Slides 14-15_Chapter 18_Claisen Rearrangment_ Youtube Video 4 Slides 16-25_Chapter 18_ TO BE DONE IN CLASS 1
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Chapter 18: Ethers, Epoxides, Thiols and Sulfides 2 O O O CO 2 CH 3 O Eplerenone (trade name Inspra) A drug prescribed to reduce cardiovascular risk in patients who have already had a heart attack O CF 3 N H (R)-Fluoxetine (trade name Prozac) A powerful antidepressant SH HO SH Dimercaprol A drug used to treat mercury and lead poisoning H 3 C S SH (Methylthio)methanethiol A compound that male mice excrete in their urine to signal females that they are fertile 1. Smith J. G., Organic Chemistry, 3 rd Ed., McGraw-Hill, 2011. 2. Klein D., Organic Chemistry, John Wiley & Sons, Inc., 2012. 3. Chemical and Engineering News, Issue: Feb 13, 2012, pp 9, ACS
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Chapter 18: Ethers, Epoxides, Thiols and Sulfides Functional Groups: ° Ethers R-O-R’ e.g. ° Epoxides ° Thiols R-S-H e.g. ° Sulfides R-S-R’ e.g. Ethers ± Ethers are compounds of formula R-O-R’ where R and R’ may be ° alkyl groups or e.g. ° aryl (benzene ring) groups or ° vinylic groups O O O O diphenyl ether Vinyl ether (IUPAC: etheroxyethene) SH S O 3
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Classification of Ethers 1. Symmetrical ethers e.g., 2. Unsymmetrical ethers 3. Cyclic ethers Nomenclature/ Naming of Ethers Common and IPAC names) ° Simple ethers with no other functional groups are named by identifying the two organic substituents and adding the word ether. ° Rules Common name: alkyl alkyl ether names 1) For simple ethers a) The alkyl groups should be named in alphabetical order.
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