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CHM 3120 midterm 2 ans key 2010

CHM 3120 midterm 2 ans key 2010 - *‘ Name Student CHM...

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Unformatted text preview: -**‘ Name: Student #: CHM 3120 Intermediate Organic Chemistry (Fall 2010) EXAM #2 Instructions: Please answer all questions in the space provided. If you require additional space use the back pages. Model kits are permitted. Time allotted: 2 hrs. 1. Provide the major product(s) expected in the following reactions. Be sure to denote relevant stereochemistry were necessary. (15 points) 5 6 a) / C02CH3 heat \ SE l+ _——> \ J CH5 INCH} #/ @ Ph /\SH (1 equiv.) Pk I-l’ b) A W {7; VS 0 THF a o- 0 EN (1 equiv.) “C" . 5 CH2=CH2 ‘ S, c) Br\/U\Cl TFH [email protected]] heat ’l" 1) CH3Li (1 equiv.) H} ‘ / / . d) n 2) H+IH20 >/ H, T 2’ HO (CH3)2CULl e) V?) THF [Gem] aw- I—lO\/\g o f) / + {CHO heat ”A ‘n ,4, \‘l‘ ‘l' 3 , H3CO 5o \ l . (ngu C , 7/3I-lC Name: Student #: 2. Predict the products from the following reactions using FMO theory. What do the orbitals in the HOMO of each example look like? Finally, clearly identify and illustrate the nature of bond rotation. (10 points) Name: Student #: 3. Consider the following molecule. Draw the LCAO representation of all the Tl? molecular orbitals. Clearly label all bonding and antibonding orbitals and show the symmetry of each molecular orbital. (10 marks) M / G) 0 Name: Student #: 4. Propose a synthesis of compound 1 starting from compound 2 and 3 and any other reagents or starting materials that you may require. For full credit ou must show Mechanism-gall enolate intermediates m You etrosynthetic anal '. (10 points) L.5 55kg“, . . awe Ph new 2 °W°+ m» COZH I) ‘ 0x0 Name: Student #: 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 Wins, all enolate intermediates w your retrosynthetic analysis. (10 points) 1‘ Name: Student #: 6. Consider the following reaction. There is a major and minor product formed. Provide the structure of either the major or minor product (your choice) and the transition state corresponding to that product. (10 points) 0 O 1) BuzBOTf, EtaN mmao n 1 +2 it 7. Name: Student #: BONUS: What is the structure of the major product in the following reaction? Draw a transition state that explains how this product is formed. (3 point . O AfiNJOKO ggfiifrm /\/U\N/l , | $ (SH; 4 l ...
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