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02152010 - detailed information about exam coverage ground...

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CH 310N – MWF 8:00 – Lecture 12 – M 2/15/2010 Graded Homework : HW#07 deadline = 4:00 p.m. on Tu 2/16 Reading Assignment : 16.11A, 16.11B, 16.11C Textbook Problems : No new problems… Last Time : Nomenclature and physical properties of aldehydes & ketones Spectroscopy of aldehydes & ketones Preparation of aldehydes & ketones (end Midterm Exam #1 coverage) Introduction to nucleophilic addition reactions Today: Today : Reversible nucleophilic substitution reactions – cyanohydrin formation and hydration Relative reactivity of aldehydes vs. ketones 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
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Unformatted text preview: detailed information about exam coverage, ground rules, etc. • Early exam students will receive e-mail with further instructions sometime late this evening… 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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