12042009 - CH 310M/318M MWF 12:00 Lecture 41 F 12/4/2009...

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CH 310M/318M – MWF 12:00 – Lecture 41 – F 12/4/2009 Last Time : Reactions of alcohols (Chapter 10) Course evaluations 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 : More reactions of alcohols (finish Chapter 10) Ethers and epoxides (Chapter 11) The final exam is scheduled for Monday, 12/14 from 9:00 a.m. to 12:00 p.m. The exam will be comprehensive , but a stronger emphasis will be placed on “new” material…a detailed “End of Semester Info” handout has been posted in Blackboard, and was also e-mailed to everyone!!! The final exam is mandatory – failure to take the exam with your “official” NO MAKE- UP/CONFLICT EXAMS WILL BE GIVEN!!! Due to space constraints and grade reporting deadlines, it is NOT POSSIBLE to take the exam with another section!!! PLEASE READ AND UNDERSTAND SECTIONS 11.1-11.3 & 11.7. YOU WILL BE RESPONSIBLE FOR THIS MATERIAL, EVEN THOUGH WE WILL NOT SPEND TIME IN LECTURE DISCUSSING IT!!!
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Acid-Catalyzed Dehydration of Alcohols Alcohols lose H 2 O upon heating with concentrated H 2 SO 4 or H 3 PO 4 . The MAJOR product is the Zaitsev alkene: CH 3 OH conc. H 2 SO 4 OR H 3 PO 4 D a b b b CH 3 + Zaitsev alkene Here’s a pattern to recognize… When an oxygen-containing organic molecule is exposed to STRONG ACID , H 2 O typically boils away… the oxygen atom will typically be PROTONATED in an acid-base reaction CH 3 OH S O O O OH H CH 3 OH H S O O O OH (resonance!!!) CH 3 H 2 O H O H R another alcohol molecule acts as the base… CH 3 O H R H REPEAT!!! E1 Mechanism!!!
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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
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This note was uploaded on 01/08/2010 for the course CH 53675 taught by Professor Bocknack during the Fall '09 term at University of Texas at Austin.

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12042009 - CH 310M/318M MWF 12:00 Lecture 41 F 12/4/2009...

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