Chem241a_Lecture_22 - Or ganic Chemistry 241a Prof. Bogdan...

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Unformatted text preview: Or ganic Chemistry 241a Prof. Bogdan Olenyuk Contact Information Office: Old Chemistry 309 olenyuk@email.arizona.edu Phone: (520) 626-0754 Course web site: http://www.chem.arizona.edu/courseweb/074/CHEM241A1_2/FrameSet.html Chapter 8: Alkynes Alkynes: Hydroboration/oxidation of alkynes Reduction of alkynes Formation of cis-alkenes Formation of trans-alkenes Oxidative cleavage of alkynes Acidity of alkynes Alkylation of acetylide anions Introduction to organic synthesis Today we will cover: Reading Assignment: McMurry (the BOOK), Ch. 8.4-8.9 Hydroboration/Oxidation of Alkynes B H 3 (borane) adds to alkynes to give a vinylic borane Oxidation with H 2 O 2 produces an enol that converts to the ketone or aldehyde Process converts alkyne to ketone or aldehyde with orientation opposite to mercuric ion catalyzed hydration Comparison of Hydration of Terminal Alkynes Hydroboration/oxidation converts terminal alkynes to aldehydes because addition of water is non-Markovnikov The product from the mercury(II) catalyzed hydration converts terminal alkynes to methyl ketones Reduction of Alkynes...
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Chem241a_Lecture_22 - Or ganic Chemistry 241a Prof. Bogdan...

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