2009_02_02_09_08_22 - Chemistry 1408 Whitesell Winter...

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Unformatted text preview: Chemistry 1408 Whitesell Winter Quarter, 2009 First Midterm Exam, Monday February 2, 2009 first name middle last name initial Student [D Number Your answers to this exam are to be only your own work. You may use no written information during this test period other than the five pages of this exam. You may not use the back of any pages for answers. Up to one week (exactly 168 hours) aficr your exam is returned you may submit it for regrading if and only if you have made NO marks on the exam except for a star (*) ON THIS PAGE next to the number(s) of the question(s) you would like regarded and your signature(s) and cheek(s) below. your signature (read the above before signing) To request regrading, sign below and check the appropriate boxe(s). your signature I would like the questions marked with a star (*) regraded (check box at right) D If you feel that we have made an addition error in your score, check the box at the right I] 1. An absorption in the infrared at 2150 is indicative of the presence of a: D Carbonyl group D Amine [:1 Alcohol M Nitrile 2. An absorption in the infrared at 1720 is indicative of the presence of a: Carbonyl group El Amine [:I Alcohol [I Nitrile 3. A broad absorption in the infrared centered at 3500 is indicative of the presence of a: E] Carbonyl group C] Amine Alcohol El Nitrile 4. The strength of the 0—0 bond in H202 is: [:l 86 E] 93 El 111 I23 36 5. Predict the expected shift for each of the carbons in 2-butanol. Put your answers in the boxes proved. C —ot — [ii — T For any 3373 carbon, add to 0.0, for each or or B substitucnt 8.0 In addition, add for each: or oxygen substituent 38.0 Y carbon—2.0 v oxygen—5.0 6 (3'5 9; 0 Your signature (in ink) 6. ' Provide a complete mechanism including curved arrows showing the flow of all electrons for the following reaction flHe OH —,. H20 / ,4 W leap?“ /l/O\ \ _ \ /. H ?. Provide a complete mechanism including curved arrows showing the flow of all electrons for the following reaction Br HBr R202 ll Ir fiogf 'H> ROD film/gr“ r—-—T> RO“H Your signature (in ink) 3 f, Br. 8. Provide the expected major organic product from each of the following reactions. Show ONLY one enantiomer for products with one center of chirality. If two centers are present in the product, you must show relative stereochemistry. You must place your answer in the box provided. Answers outside the boxes will not receive credit. HBr 1) BZH6 —_—’. 2) NdOH H202 H3CCO3H _——,.. “\\‘\\O H \ N aOH —_—* Br Your signature (in ink) 9. The proton nmr spectrum shown below was obtained on a compound with the formula: Gel-114. Provide a structure in the box provided that is consistent with the spectrum. Your signature (in ink) 5...
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