MWF_22 - Organic Lecture Series CH 310/318 M LECTURE 22...

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Organic Lecture Series 1 CH 310/318 M LECTURE 22 Textbook Assignment: Chapter 7- Alkynes Today’s Topics: Alkyne Alkyne reactions reactions Notice & Announcements: POW 7 posted Organic Lecture Series 2 Alkynes Alkynes Chapter 7 Chapter 7
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Organic Lecture Series 3 • Alkynes add one mole of bromine to give a dibromoalkene. – Addition shows anti stereoselectivity. CH 3 CC C H 3 Br 2 3 COOH, LiBr H 3 C 3 anti addition ( E )-2,3-Dibromo-2-butene 2-Butyne + Addition of X Addition of X 2 Organic Lecture Series 4 – The intermediate in bromination of an alkyne is a bridged bromonium ion. Addition of X Addition of X 2 H 3 H 3 Br Br Br H 3 C CH 3 Br H 3 H 3 Br H 3 C Br Br CH 3
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Organic Lecture Series 5 • Alkynes undergo regioselective addition of either 1 or 2 moles of HX, depending on the ratios in which the alkyne and halogen acid are mixed. 2,2-Dibromopropane 2-Bromopropene Propyne CH 3 CCH Br HBr 3 C=CH 2 3 3 Addition of HX Addition of HX Follows Markovnikov Markovnikov ’s rule, but why? rule, but why?
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This note was uploaded on 11/07/2010 for the course CH 101 taught by Professor Dude during the Spring '10 term at Williamson.

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MWF_22 - Organic Lecture Series CH 310/318 M LECTURE 22...

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