Lecture3-Aromatics-1

Lecture3-Aromatics-1 - Announcements v Re w S ssion on...

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9/21/11 Announcements v Review Session on Monday 2:00-4:00 pm. Dave and Ida will host. v My office hours will be switched on Monday to 4:00- 6:00 pm. v Exam I on Wednesday. v Exam I will cover chapters 13-15 plus study guides 1 (page 1 only) and 2. Pay attention to my exclusions. 11
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9/21/11 22 Predict the product of this Diels-Alder Reaction. A B C O 2 N NO 2 O + heat O NO 2 NO 2 O NO 2 NO 2 O NO 2 NO 2 O NO 2 NO 2 D E No Reaction
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9/21/11 33 Draw the MO diagram for 1,3,5- hexatriene. 2 nodes 1 2 3 4 5 6 3 nodes 1 2 3 4 5 6 4 nodes 1 2 3 4 5 6 1 node 1 2 3 4 5 6 5 nodes 1 2 3 4 5 6 0 nodes 1 2 3 4 5 6 D C B E A F Draw and select The HOMO.
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9/21/11 44 Draw the MO diagram for 1,3,5- hexatriene. 2 nodes 1 2 3 4 5 6 3 nodes 1 2 3 4 5 6 4 nodes 1 2 3 4 5 6 1 node 1 2 3 4 5 6 5 nodes 1 2 3 4 5 6 0 nodes 1 2 3 4 5 6 E
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9/21/11 55 Synthesis Problem from Workshop 1 part II. Synthesize using any reagents containing 4 carbons or less. conc. H 2 SO 4 OH H 3 O + O Li +
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9/21/11 66 Synthesis Problem from Workshop 1 part II. Synthesize using any reagents containing 4 carbons or less. conc. H 2 SO 4 OH 1 2 3 8 6 4 5 7 9 1 0 H 3 O + O BrMg + PCC OH Mg Br PBr 3 OH OH H 2 Lindlar 2) H 3 O + MgBr 1) O 1) 2) H 3 O + O
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9/21/11 77 Synthesis Problem I Synthesize starting from benzene and any reagents containing 3 carbons or less. H O
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9/21/11 Predict the major product. 88 O + heat O O or O O O O O O O O
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9/21/11 O O O O O O O O O δ + δ - O δ + δ - O 1 2 O O 4 3 2 1 O O Regiochemistry is: 1-2 called ”ortho” or 1-4 called “para” Regiochemistry 99
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9/21/11 Substituents in the 1-3 or “meta” position are not seen because the charges don’t line up O δ + δ - O δ + δ - δ + O δ + δ - O O O O O Regiochemistry 1010
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9/21/11 t t c c m m m m t c t c s-trans s-ci s m m t c t c + c c t t m m N + Which of these could be the product? A B C N N N N 1111
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9/21/11 Predict the major product. 1212 O + heat O O or O O O O O O O O Diastereomers Enantiomer s
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9/21/11 Stereochemistry m m t c t c + O c c t t m m c c t t m m O O or endo exo 1313
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9/21/11 O O But-3-en-2-one Thedienophile is actually a diene if you count the C=O doublebond LUMO HOMO Stereochemistry 1414
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9/21/11 Normal butadiene plus ethene interaction A LUMO HOMO A HOMO A LUMO HOMO LUMO endo exo O O endo Wins! Stereochemistry 1515
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9/21/11 t t c c m m s-trans s-cis m m t c t c + O O t t c c H m m c c t t m m O H Stereochemistry endo Wins! TheEWG will be cis to the “t” groups. 1616
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9/21/11 O t t H m m O O O H t t m m + O O t t m m furan endo Wins! endo 1717
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9/21/11 Predict the major product. 1818 O + heat O O or O O O O O O O O Diastereomers Enantiomer s
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9/21/11 t t c c m m m m t c t c s-trans s-ci s m m t c t c + c c t t m m Which of these could be the product? A B C + O O O O O 1919
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9/21/11 O O O δ + δ - O BF 3 O B F F F O B F F F O δ + B F F F δ - EWG How can we makeit better? Add a Lewis acid catalyst likeBF3 or AlCl3 H O BF 3 H O Reaction works without catalyst.
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