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310NSp0802082008 - weekend and will be discussed in lecture...

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CH 310N – MWF 8am – Lecture 11 – F 2/8/2008 Graded Homework : HW#05 deadline = 3:00 p.m. on Mon 2/11 (last graded HW due before Midterm Exam #1) Reading Assignment : Sections 16.7, 16.8 Textbook Problems : 16.18-16.22, 16.43(a-c), 16.44(a-c) (last book problems for Midterm Exam #1) Last Time : Mechanisms of cyanohydrin formation and hydration reactions of aldehydes & ketones Relative reactivity of aldehydes vs. ketones Today : Relative reactivity of aldehydes vs. ketones (continued…) Irreversible nucleophilic addition reactions Grignard addition Hydride reduction Midterm Exam #1 is scheduled for Thu 2/14 from 7:00 to 9:00 p.m. Students who signed up to take the conflict exam will receive e-mail on Monday evening with further instructions Detailed information about the exam (coverage, ground rules, room assignments, etc.) will be posted on the website sometime this
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Unformatted text preview: weekend, and will be discussed in lecture on Monday… 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 2.8 x 10 4 Cl 3 CCH=O too large to measure (CF 3 ) 2 C=O 37 ClCH 2 CH=O 10 (ClCH 2 ) 2 C=O 8.3 x 10 –3 PhCH=O 1.2 x 10 –7 Ph 2 C=O 0.5–1.0 (CH 3 ) 2 CHCH=O 6.6 x 10 –6 1.0 CH 3 CH=O 1.4 x 10 –3 (CH 3 ) 2 C=O 2.2 x 10 3 CH 2 =O K eq Ketone K eq Aldehyde Ph C C H 3 O 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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