Chem241a_Lecture_22

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 [email protected] 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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