lecture 14 - Organic Lecture Series CH 310/318 M LECTURE 14...

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Organic Lecture Series 1 CH 310/318 M LECTURE 14 Textbook Assignment: Begin Chap 8 Today’s Topics: Alkynes: Reactions Alkynes: Reactions Notice & Announcements: (HW 5 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. 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 Addition of X Addition of X 2
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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? Organic Lecture Series 6 – The intermediate in addition of HX is a 2° vinylic carbocation in preference to a 1° vinylic carbocation.
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This note was uploaded on 10/20/2011 for the course CH 310 M taught by Professor Iverson during the Fall '09 term at University of Texas at Austin.

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lecture 14 - Organic Lecture Series CH 310/318 M LECTURE 14...

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