Lecture2-DielsAlder(1)-1 - Announcements v Re S ad tudy...

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9/21/11 Announcements v Read Study Guide 1 (page 1 only) and Study Guide 2. v Do not forget to register your i>clicker through Blackboard. v For Friday: read chapter 14 (exclude 14.7C, 14.10-14.11) & chapter 15 (15.1-15.9). v The next online quiz deadline is Fri. 5 pm. The general schedule is: v Live at Fri 5 pm until Tue 7 am. v Live at Tue 5 pm until Fri 5 pm. 11
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9/21/11 CHE 321 Final Notes v CHE 321 Final: Average = 95.7 (53%). Last year’s average = 77.7 (43%). Two students earned A on the final exam (163 and 170). v Adjustment made was generous (course gpa about B-). v Three students performed better on Final than on their adjusted course total: v C to C+ v B- to B v B+ to A- 22
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9/21/11 Question 1 (Question 4 Form 3) 33 12 % of the class answered correctly 25 % 18 % 29 % 15 % WS3 Pt II H O
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9/21/11 Question 19 (Question 2 Form 3) 44 36 % of the class answered correctly 39 % How do we solve this problem? Use the pKa table
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9/21/11 Question 9 (Question 12 Form 3) 55 41 % of the class answered correctly WS3 Part I
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9/21/11 Alkadienes 66 Three Types isolated conjugated cumulene 1,3-pentadiene 1,4-pentadiene allene C C C H H H H
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9/21/11 Propose a synthesis of this diene. Your starting materials can have four or fewer carbons. O Li H 2 SO 4 H O Li H 2 SO 4 Li O H 2 SO 4 i. ii. iii. A i. B ii. C iii. D i. or ii. E i. or iii. F ii. or iii. G i. or ii. or iii. Which synthesis would work? 77
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9/21/11 88 Study Guide 1 (Page 1 Only) How to MAKE a conjugated diene Two Methods conc. H 2 SO 4 OH OR OH Li O + H 3 O + + H 3 O + Li O Br OR Br NaOEt OH OR OH PBr 3 NBS + H 2 Lindlar Br
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9/21/11 How much energy do you gain from conjugation? 99
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9/21/11 Bond lengths of conjugated dienes 1010 1.34 Å 1.47 Å 1.34 Å H 3 C CH 3 H 2 C CH 2 1.54 Å ~1.34 Å 1.54 Why is the bond length of the C2-C3 bond shorter than the C-C bond in ethane? A. The C-C bond in ethane is not sterically hindered. B. The C-C bond in ethane is between two sp3 orbitals, and in butadiene, it is between 2 sp2 orbitals. C. None of these reasons. D. Both of these reasons.
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9/21/11 A x S x x E A x S x Draw a MO enery level diagram for butadiene. ethene HOMO LUMO Your diagram should look like this. 1111
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9/21/11 A x S x x E A x S x Draw a MO enery level diagram for butadiene. Which of these MOs is the HOMO? Which of these MOs is the LUMO? Which of these MOs is not possible? a. b. c. d. e. 1212
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9/21/11 At home, draw a Molecular Orbital diagram for hexatriene 0, 1, 2, 3, 4, 5 nodes LUMO HOMO 1313
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9/21/11 171 nm Ground State Excited State h ν light π π π π transition 1414
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9/21/11 H H H H 290 nm 171n m L copene 217nm 505nm 10 conjugated double bonds 1515
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9/21/11 217 nm 171 nm Ground State Excited State h ν light π π π π transition 1616
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CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 A B C Which of these three steroids has the longest wave length absorption band? 324 nm
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This note was uploaded on 09/21/2011 for the course CHEM 213CCF taught by Professor Staff during the Spring '08 term at Pennsylvania State University, University Park.

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Lecture2-DielsAlder(1)-1 - Announcements v Re S ad tudy...

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