Midterm 2 Answer key 2008

Midterm 2 Answer key 2008 - 3 l {Ale P I Name: Mm __._=%...

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Unformatted text preview: 3 l {Ale P I Name: Mm __._=% Student#: Intermediate Organic Chemistry (Fall 2008) EXAM #2 Instructions: Please answer all questions in the space provided. If you require additional space use the back pages. Model kits are permitted. There are 5 questions. Time allotted: 3 hours 1 . Predict the major product(s) from the following reactions. Be sure to show relevant stereochemistry where required. (10 points) “co 0 a) H3C0 .1. ‘\ W 1) CH3Li (1 equiv.) H3 b) ('3 2) HVHZO @ C) HO Name: Student #: 2. 3) Consider the following reaction. What is the structure of the product formed in this reaction? Using FMO theory, rationalize the stereochemistry of the product. What is the nature of bond rotation ifi‘his reaction? (10 points) Name: Student it: 3. a) Consider the following diene. Draw the LCAO representations of- all the 1: molecule orbitals. Identify all molecular orbitals, the distribution of all 7: electron, bonding and antibonding orbitals and the HOMO and LUMO. (10 points) Name: Student #2 3. b) Consider the following reaction. What are the structures of the major a_n_d_ minor products? Using an analysis of the frontier molecular orbitals explain why the major product is favored (assume the reaction is irreversible). Is the major product a kinetic or thermodynamic product? (10 points) Name: Student #: 4. Propose a synthesis of compound 1 starting from compound 2 and any other reagents or starting materials that you may require. For full credit you must show all intermediates glad your retrosynthetic analysis. (10 points) Name: Student #: 5. Propose a synthesis of compound 1 starting from compounds 2, 3 and 4 and any other reagents or starting maten'als that you may require. For full credit you must show detailed mechanisms and all enolate intermediates Hint: you will need to perform a conjugate addition. (10 points) ...
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Midterm 2 Answer key 2008 - 3 l {Ale P I Name: Mm __._=%...

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