MWF_22 - Organic Lecture Series CH 310/318 M Textbook...

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Organic Lecture Series 1 CH 310/318 M LECTURE 22 Textbook Assignment: Chapter 7 Today’s Topics: Alkynes: reactions & preparations Alkynes: reactions & preparations Notice & Announcements: HW 6 posted Organic Lecture Series 2 Alkynes Alkynes Chapter 7 Chapter 7
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Organic Lecture Series 3 – Terminal alkynes can also be converted to alkyne anions by reaction with sodium hydride or lithium diisopropylamide (LDA). – Because water is a stronger acid than terminal alkynes, hydroxide ion is not a strong enough base to convert a terminal alkyne to an alkyne anion. Na + H [(CH 3 ) 2 CH] 2 N Li + Sodium hydride Lithium diisopropylamide (LDA) K eq = 10 -9.3 p K a 15.7 p K a 25 - - + + (Stronger acid) (Weaker acid) HC CH C OH H 2 O Acidity Acidity Organic Lecture Series 4 Alkylation of Alkylation of Alkyne Alkyne Anions Anions • Alkyne anions are both strong bases and good nucleophiles. • They participate in nucleophilic nucleophilic substitution substitution reactions with alkyl halides to form new C-C
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MWF_22 - Organic Lecture Series CH 310/318 M Textbook...

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