MWF_19 - Organic Lecture Series CH 310/318 M LECTURE 19...

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Organic Lecture Series 1 CH 310/318 M LECTURE 19 Textbook Assignment: Chapter 7- Alkynes Today’s Topics: Alkenes Alkenes - Reactions Reactions Notice & Announcements: POW 6 posted Organic Lecture Series 2 • Hydroboration Hydroboration : The addition of borane, BH 3 , to an alkene to form a trialkylborane. • Borane dimerizes to diborane, B 2 H 6 . Borane Diborane 2BH 3 B 2 H 6 Borane HB H H 3CH 2 =CH 2 CH 3 2 B 2 3 2 3 Triethylborane (a trialkylborane) + Hydroboration Hydroboration /Oxidation /Oxidation Not exam material Not exam material
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Organic Lecture Series 3 • Hydroboration is both – regioselective (boron bonds to the less hindered carbon) – and syn stereoselective. CH 3 H BH 3 BR 2 HH 3 C H + 1-Methylcyclopentene (Syn addition of BH 3 ) (R = 2-methylcyclopentyl) Hydroboration Hydroboration /Oxidation /Oxidation Organic Lecture Series 4 – Concerted regioselective and syn stereoselective addition of B and H to the carbon-carbon double bond.
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MWF_19 - Organic Lecture Series CH 310/318 M LECTURE 19...

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