23 - into another functional group during the course of the...

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CH 310M/318M – TTh 8am – Lecture 23 – T 4/8/2008 Reading Assignment : Sections 8.6, 8.8 Graded Homework : HW#16 deadline = 3:00 p.m. on Thu 4/10 HW#17 deadline = 3:00 p.m. on Mon 4/14 (last graded HW due before Midterm Exam #3) Last Time : Alkylation of acetylide anions Preparation of alkynes from vicinal and geminal dihalides Electrophilic addition reactions of alkynes Textbook Problems : 7.11, 7.14, 7.17, 7.18, 7.20-7.25 Today : Keto-enol tautomerism Oxymercuration (acid-catalyzed hydration) of alkynes Reduction reactions of alkynes Solving synthesis problems in organic chemistry (download the online handout!!!)
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There are 3 types of operations involved in organic synthesis: Functional group transformations Most of the reactions you have learned at this stage are examples of a functional group transformation – one functional group is converted
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Unformatted text preview: into another functional group during the course of the reaction Control of stereochemistry If a particular stereoisomer of the target is desired, use of stereoselective reactions will be necessary during the course of the synthesis. Several of the reactions you have learned thus far allow for stereochemical control (syn addition vs. anti addition) Formation of CC bonds Since the goal of organic synthesis (in the real world, at least) , is to build up complex target compounds from simple (and inexpensive) starting materials, reactions that form carboncarbon bonds are typically of tremendous importance in synthesis. At this stage you only know one reaction that leads to formation of a new CC bond alkylation of an acetylide ion by treatment with a methyl or 1 alkyl halide....
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23 - into another functional group during the course of the...

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