Chemistry 310 Fall 2017

Schedule & Assignments

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Online quizzes are due by 8 am the day of class!

Day Topics Readings Etc. (do. before. class.)
Aug. 23rd Introduction to the course. Important concepts from Chem 120/240. No Quiz. Study Question 0 (concept review) We will start this in class, I will bring copies.
Aug. 25th Acids & bases. Effect of structure on pKa. Energy diagrams. Why you don't need Table 1.3 Online Quiz! McBeg pgs 1-11. Know Table 1.1 Study Table 1.2 See also Organic Arrows and Biochemical Functional Groups McBeg problems 1.1acdegh, 1.3
Aug. 28th Acids & bases con't. Online Quiz! McBeg problems 1.5, 1.6 Look at Table 1.2: What explains the huge difference in pKa between a ketone and a β-ketoester? Strongly suggest you look at Karty sections 6.1, 6.2ab, 6.3, 6.4, 6.5, 6.6ade
Aug. 30th Effect of structure on acidity and reactivity, con't. Electrophiles & nucleophiles. We will do this study question in class. Please also look at this and read McBeg pgs 11-12, do problem 1.2 We may start on section 1.3 depending upon progress.
Sept. 1st Electrophilic additions to alkenes. Online Quiz! on functional groups, acid-base concepts, nucleophiles, electrophiles. In Class Quiz! on acid-base concepts (last half of class). Read MgBeg section 1.3 on which we will expand greatly.
Sept. 4th Electrophilic additions to alkenes, con't.
Sept. 6th Electrophilic additions in action, oh my! Try McBeg problem 1.8c Download Study Question 2 give it a try and bring to class.
Sept. 8th More action packed electrophilic additions! And, we'll start on SN1 and E1 mechanisms as time permits (note: we managed to cover SN2 reactions). Download Study Question 2a give it a try and bring to class. In anticipation of Monday, please download Chimera, install it, launch it, register it, and make sure it works. Also download and unzip these files to have ready for Monday. Finally, please read McBeg Section 1.5, and Section 1.9 about E1 (only a few sentences). In Section 1.5, pay close attention to the last two sentences in the first paragraph. Study all figures carefully.
Sept. 11th Cholesterol Biosynthesis Download Oxidosqualene Cyclase (what a mouthful!) and bring to class. Bring your computer with working Chimera to class! Before class study McBeg Fig. 3.23 (look at how the carbon chains build up), study Figs. 3.25 and 3.26 carefully and try to understand all the steps shown.
Sept. 13th Nucleophilic additions to carbonyls New Material Read in McBeg Section 1.6, the first section (pgs 19-22), the section on acetal formation (pgs 25-27) and the section on imine formation (pgs 23-25). Please review Tips for Drawing Mechanisms. We know enough now that this ought to be helpful. After you do the reading, take a look at Taxonomy of Acetals and Ketals and Parallels and Analogies Among Carbonyl Additions. Follow-Up Material from previous classes and review Please be sure to complete your study of the OSC mechanism and details of the active site. Please do Study Question 3.
Sept. 15th Carbonyl additions con't. Before class, please work on Study Question 3b. Try these problems: 2.26, 2.28. For both of these, think about hidden carbonyls. Hidden carbonyls lead to carbonyls, which can be attacked. Also, problem 2.28 runs the carbonyl addition process backwards, until it runs it forward (sounds nonsensical, but it's exactly what's going on, you'll see). Feel free to re-draw the structures by removing all the parts that are not changing. Focuses the mind! Last part of class there will be an in class quiz.
Sept. 18th Carbonyl additions con't. and Practice of All Kinds Try the following McBeg questions. Some are general practice, some are closely linked to our recent mechanisms: 1.7, 1.16, 1.17, 1.18 (think about resonance to get the nucleophile in the right place), 1.19 (think about 1.18, 1.7a and 1.7c for hints), 2.12 Try Study Question 2b to review some of the earlier material
Sept. 20th Bring your questions! Bring your questions!
Sept. 22nd Exam #1 Exam #1
Sept. 25th Exam follow-up, loose ends on AdNC=O, conjugate additions Read conjugate additions on pg. 27, Sec. 1.7
Sept. 27th DePauw Dialogue. No class!
Sept. 29th Intro to SNC=O Read McBeg sections 1.7 and 3.1 Using what you learn in 1.7 draw a mechanism for the reaction shown in the middle of pg. 118. Do problem 3.14 but use Chimera. Try Karty problems 20.52, 21.52, 21.53 (Karty is on reserve in Prevo Library). Download this scheme and bring to class. Download this folder containing Chimera files to use with Study Question 5
Oct. 2nd Carbonyl condensations: aldol and Claisen condensations Read McBeg section 1.8 carefully! Do problems 1.8ab, 1.9, 1.10. Try Karty problems 20.42.
Oct. 4th Practice with carbonyl condensations Do as much of Study Question 6 as possible before class.
Oct. 6th Practice with carbonyl condensations. Quiz 2nd half of class Work problem 1.13
Oct. 9th Introduction to polyketides. Study Question 6a
Oct. 11th Oh the things you can do with polyketides! The Polyketide Game! Work problem 1.21 Read McBeg section 3.4 (skip step 3) and section 7.4 (don't worry about the references to the mysterious "cytochrome P450")
Oct. 13th Questions about polyketides? Study Question 7a Quiz 2nd half of class!
Oct. 23rd Review questions (coming soon) Some practice problems in anticipation of the exam: 1.12, 1.14.
Oct. 25th Bring your questions! Bring your questions!
Oct. 27th Exam #2 Exam #2
Oct. 30th DERA paper discussion
Nov. 1st DERA paper discussion con't.
Nov. 3rd Glycolysis, review carbohydrate stereochemistry etc. Read McBeg 4.1, 4.2, review 2.1, 2.3
Nov. 6th Glycolysis con't Try McBeg problems 4.7, 4.9, 4.10, 4.12
Nov. 8th Fates of Pyruvate, Citric Acid Cycle Read McBeg 4.3, 4.4, Try problems 4.1, 4.2, 4.5
Nov. 10th Citric Acid Cycle con't, electrochemical aspects Quiz 2nd half of class!
Nov. 13th Transamination Reactions Read McBeg 5.1 Try problems 5.3, 5.5, 5.9
Nov. 15th Transaminations con't Take a good look at Table 5.10, then try problems 5.14 and 5.19. Try study Questions 8 and 10
Nov. 17th Bring your questions! Bring your questions!
Nov. 20th Exam #3 Exam #3
Nov. 27th
Nov. 29th
Dec. 1st
Dec. 4th
Dec. 6th
Dec. 8th
Dec. 12th 8:30 am Final Exam Final Exam

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