02172010 - organometallic reagents; hydride reduction...

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CH 310N – MWF 8:00 – Lecture 13 – W 2/17/2010 Reading Assignment : 16.7 Textbook Problems : 16.4, 16.12, 16.18-16.21 Last Time : Reversible nucleophilic substitution reactions – cyanohydrin formation and hydration Relative reactivity of aldehydes vs. ketones Today : Relative reactivity of aldehydes vs. ketones (continued…) Midterm Exam #1 is scheduled for Thursday, 2/18 from 7:00 to 9:00 p.m. Last name A–M report to FAC 21; last name N–Z report to JGB 2.324 You must take the exam in your assigned room! 10 points will be deducted from the raw score if you take the exam in the wrong room!!! Be sure to look at the “Exam Information Sheet” (available in Blackboard) for detailed information about exam coverage, ground rules, etc. Early exam students should have received e-mail with further instructions on Monday evening Irreversible nucleophilic addition reactions – reactions with
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Unformatted text preview: organometallic reagents; hydride reduction reactions GOOD LUCK ON THE EXAM!!! NO BOCKNACK OFFICE HOURS ON FRIDAY!!! Both reactions we have just discussed are equilibrium reactions. Which side of the reaction is favored at equilibrium??? Consider the data below for the following general reaction: R C R' O + H 2 O OH C OH R' R K eq Aldehyde K eq Ketone K eq CH 2 =O 2.2 x 10 3 (CH 3 ) 2 C=O 1.4 x 10 –3 CH 3 CH=O 1.0 6.6 x 10 –6 Ph C C H 3 O (CH 3 ) 2 CHCH=O 0.5–1.0 Ph 2 C=O 1.2 x 10 –7 PhCH=O 8.3 x 10 –3 (ClCH 2 ) 2 C=O 10 ClCH 2 CH=O 37 (CF 3 ) 2 C=O too large to measure Cl 3 CCH=O 2.8 x 10 4 Some observations : • Aldehydes undergo nucleophilic addition more readily than ketones • Nearby electronegative groups make carbonyl addition more favorable • Aromatic substituents make carbonyl addition less favorable...
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This note was uploaded on 04/07/2010 for the course CH 310n taught by Professor Iverson during the Spring '08 term at University of Texas.

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02172010 - organometallic reagents; hydride reduction...

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