Chem 317 - practice exam 2 key

Chem 317 - practice exam 2 key - CHEMISTRY 317- WINTER 2007...

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Unformatted text preview: CHEMISTRY 317- WINTER 2007 EXAM 2 — Tuesday, March 6th NAME: [<5 Y (last) (first) 1. This exam consists of 5 questions. Do the ones you know how to do first, then come back to the others if you have time. 2. If you run out of space working a problem, use the back of that page and indicate on the front that you have done so. 3. Please, scrupulously avoid even casual glances at other exams! ! ! l !! QUESTION VALUE SCORE - — - _ - - Name: 1. Circle the correct response(s) for each of the following: (3 ea) 7- a) circle the most basic compound Co” o b) which of the following would be expected to give the highest equilibrium concentration of hydrate upon reaction with water (acidic)? c) circle the compound with the highest expected boiling point 0 H O/NHz x/k /H\/\/ gr: :1) circle ALL compounds that would give a ositive Tollen's test 6) ALL correct names for 2-methyI-3—oxopentane thyl isopropyl ether isopropoxy 2-ethano f) circle the bond that is shortest and strongest C='C @ 0—0 0—0 C—H 2-ethoxypropane Name: y 7. 2. Complete each of the short answer questions below: a) The questions below refers to structures AB, and c below. Answar each with a letter. letters, or the word 'none'. H CH0 :3 0a. H0 H 3 OH H HO 0H 0 on H “2 OH OH OH C HOH ,4 C __;.— A B 1) Which of the compounds above are reducing sugars? 2) Which ol the compounds above contain a hemiacetal? C 3) Which ot the compounds above show an optical rotation? A! 6 g; 4) Which of the compounds above are carbohydrates? . Ar & I. C‘ b) What product would you get it you treated A lrom part a) above with NaBH4? Draw the product. “L0H Ho H H o 6} Match the names below with any structures given (the structures may not all match something. and there may be more than one answer tor each). 0 - . ti 3% H \ 2) enamine B _ fi QN’WA U m E 3 3)imine Ll IT) A B H C D g CN 4) hydra‘e HEN H Cam OI AA K D )EA F G H l J 5) azide d) The rate tor lorrnation of an imine from an aldehyde and a t” amine is optimal at pH ~4.5. Explain why the rate is expected to be louver at 1) lower pH and 2) higher pH. Be specific for futl credit. 1) at: law P“, OHM twin: is pmtonakot email is Mel a good] nucleophilc ENHZ 4- H’f : Name: K E y 3. Complete each of the reactions below. Be careful to include any stereo— and regio- chemistry if needed. (3 ea) a) \ H20, Brz /0 + '———i / w- b) fit) NaBH4. CH3OH Q,” 0 Ho 0 c) Ht CH30H on . W OLU3 /\ d) 0 0 #9. w. H o 3 _2__.. + 1 EtOH 61*; H e) H —\ 1) Hg(OAc)2I 2) NaBH4 1) 2 eq CH3MgBr 2) H+, H20 A9(NH3)2(OH) Name: Z W 4. Use correct arrow formalism (including all steps) to show the mechanisms for the following transformations: M + a) j + H20 ___'__l_ HO/\/\OH + CHZO 4 raw—w; "H §o§l o “LN Ji" Hab‘ ‘ “ C53)“ (0; , \OH 0) ’IL 7L 4 i OH/HHZ‘O pat-t fl}? [\OH 1: [\oH ——-——§ \ n v ‘— fi / e r... 0 Aé”; 0A0” QAOAOH b) CW / Name: P 5. Show how you would prepare the following compound efficiently using What is given and any other necessary reagents. __.O ——o ...
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This test prep was uploaded on 04/09/2008 for the course CHEM 317 taught by Professor Kantorowski during the Fall '08 term at Cal Poly.

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Chem 317 - practice exam 2 key - CHEMISTRY 317- WINTER 2007...

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