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310NSp0802082008
Course: CH 310N, Spring 2008School: University of Texas
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310N CH MWF 8am Lecture 11 F 2/8/2008 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) Graded Homework: HW#05 deadline = 3:00 p.m. on Mon 2/11 Last Time: (last graded HW due before Midterm Exam #1) Mechanisms of cyanohydrin formation and hydration reactions of aldehydes & ketones Relative reactivity of aldehydes...
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310N CH MWF 8am Lecture 11 F 2/8/2008
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)
Graded Homework: HW#05 deadline = 3:00 p.m. on Mon 2/11 Last Time:
(last graded HW due before Midterm Exam #1)
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, rules, ground room assignments, etc.) will be posted on the website sometime this 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: O C R Aldehyde CH2=O CH3CH=O (CH3)2CHCH=O PhCH=O ClCH2CH=O Cl3CCH=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
Keq + R' H2O Keq 2.2 x 103 1.0 0.51.0 8.3 x 103 37 2.8 x 104
OH R C OH R'
Ketone (CH3)2C=O
O C Ph CH3
Keq 1.4 x 103 6.6 x 106 1.2 x 107 10 too large to measure
Ph2C=O (ClCH2)2C=O (CF3)2C=O
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