310NSp0802062008 - mail confirming their eligibility....

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CH 310N – MWF 8am – Lecture 10 – W 2/6/2008 Graded Homework : HW#04 deadline = 3:00 p.m. on Thu 2/7 HW#05 deadline = 3:00 p.m. on Mon 2/11 (last graded HW due before Midterm Exam #1) Reading Assignment : Sections 16.5, 16.11 Textbook Problems : No new problems… Last Time : Carbenoids – the Simmons-Smith reaction (end Chapter 15) (nomenclature & physical properties of aldehydes & ketones). YOU WILL BE RESPONSIBLE FOR THIS MATERIAL, EVEN THOUGH WE WON’T DISCUSS IT IN LECTURE!!! Introduction to nucleophilic addition reactions Today : Mechanisms of cyanohydrin formation and hydration reactions of Relative reactivity of aldehydes vs. ketones Students who signed up to take any conflict exam should have received e-
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Unformatted text preview: mail confirming their eligibility. Contact me ASAP if you did not!!! 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 0.51.0 (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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This note was uploaded on 08/20/2008 for the course CH 310n taught by Professor Iverson during the Spring '08 term at University of Texas at Austin.

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310NSp0802062008 - mail confirming their eligibility....

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