TTh_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: Chapter 7- Begin Today’s Topics: Alkenes Alkenes - Reductions Reductions - Notice & Announcements: POW 7 posted Organic Lecture Series 2 • Treatment of an alkene with ozone followed by a weak reducing agent cleaves the C=C and forms two carbonyl groups in its place. In the following example, the weak reducing agent is dimethylsulfide, (CH 3 ) 2 S. Propanal (an aldehyde) Propanone (a ketone) 2-Methyl-2-pentene CH 3 O O 3 C=CHCH 2 3 1. O 3 2. (CH 3 ) 2 S 3 CCH 3 + HCCH 2 3 Oxidation with O Oxidation with O 3
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Organic Lecture Series 3 – The initial product is a molozonide which rearranges to an isomeric ozonide. Acetaldehyde 2-Butene O CH 3 CH=CHCH 3 O 3 (CH 3 ) 2 S 3 3 CH-CHCH 3 OO O C O C H 3 H H 3 C A molozonide An ozonide Oxidation with O Oxidation with O 3 Organic Lecture Series 4 • Most alkenes react with H 2 in the presence of a transition metal catalyst to give alkanes. – Commonly used catalysts are Pt, Pd, Ru, and Ni. – The process is called catalytic reduction catalytic reduction or, alternatively, catalytic hydrogenation catalytic hydrogenation. – Addition occurs with syn stereoselectivity. + H 2 Pd Cyclohexene Cyclohexane 25°C, 3 atm Reduction of Alkenes Reduction of Alkenes
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Organic Lecture Series 5 • Mechanism of catalytic hydrogenation.
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TTh_14 - Organic Lecture Series CH 310/318 M LECTURE 14...

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