05072010 - CH 310M/318M - Lecture 43 F 5/7/2010 Textbook...

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CH 310M/318M - Lecture 43 F 5/7/2010 The final exam is scheduled for Wednesday, 5/12 from 7:00 to 10:00 p.m. Room & seat assignments will be posted in the “My Grades” area of Blackboard this weekend. You must go to your assigned room, and sit in your assigned seat to take the exam!!! The exam will be comprehensive , but a stronger emphasis will be placed on “new” material…the detailed “End of Semester Info” handout is now available in Blackboard… READ IT!!! The final exam is mandatory failure to take the exam at the NO MAKE-UP/CONFLICT EXAMS WILL BE GIVEN!! ! Last Time : Reactions of alcohols (continued…) Textbook Problems : 11.10-11.12, 11.15-11.17, 11.19, 11.21, 11.23, 11.24, 11.27, 11.29-11.37, 11.39, 11.42-11.44 Today : Le Chatelier’s Oxidation reactions of alcohols (end Chapter 10) Ethers and epoxides (Chapter 11)
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Acid-catalyzed dehydration works BEST for 3° and 2° alcohols (carbocation stability) 1° alcohols react via a combination of E1 and E2 mechanisms see page 392 in the textbook for an example Acid-catalyzed DEHYDRATION of an alcohol is the REVERSE of the acid- catalyzed HYDRATION of an alkene: CH 3 + H 2 O H 2 SO 4 (cat.) CH 3 OH conc. H 2 SO 4 , D AN EQUILIBRIUM!!! To control which structures are favored when the system reaches equilibrium, use Le Chatelier’s principle… …when a stress is applied to a system at equilibrium, the position of the equilibrium shifts in the direction that relieves the stress To favor the ALCOHOL, use a large excess of H 2 O (e.g. as solvent) To favor the ALKENE… …use CONCENTRATED acid (i.e. little H 2 O present as solvent) REMOVE H 2 O as it forms (by heating)
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Oxidation Reactions of Alcohols In organic chemistry, OXIDATION typically involves formation of MORE C O bonds and/or FEWER C H bonds Alcohols are oxidized to CARBONYL COMPOUNDS upon treatment with an
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05072010 - CH 310M/318M - Lecture 43 F 5/7/2010 Textbook...

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