fall02-mt2-Pedersen-exam

fall02-mt2-Pedersen-exam - Dr. Steven Pedersen November 4,...

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Unformatted text preview: Dr. Steven Pedersen November 4, 2092 Chemistry 3A Midterm #2 Student name: _ _____________________________ __ Student signature: ___________________________________ TA’s name or section number:_ __________ Problem 1 (30 pts) Problem 2 __ (36 pts) Problem 3 (14 PtS) Problem 4 (48 pts) Problem 5 __ (45 pts) Problem 6 __ (27 pts) Total Points __ (200 pts) No Calculators Allowed Be Sure Your Exam has 10 Pages Be Sure To Try All Parts of Each Problem! Organic Lingo 1A. Provide a systematic name for the following compounds. Use common nomenclature for any branched substituents. (30 pts) JOLI/ Br ; ""OH I H CI B. Draw a structure for the following names. For cycloalkanes use flat rings. For all others use bond-line notation. o (S)-4-chIoro-2,2-dimethy|-1-hexan0| o (1 Fl,4S)-4-ethyI-1-fluoro-1-iodo-3,3-diisopropylcyclohexane C. Van der Waals forces are made up of Induced Dipole Induced Dipole (IDID), Dipole Induced Dipole (DID) and Dipole Dipole (DD) interactions. On the diagram below indicate which one of these best represents the interaction taking place in each box. Mirror, Mirror on the Wall 2. (36 pts) For each pair of molecules use one term (and only one) that best describes their relationship to one another. Minus one point for every wrong answer. The terms to choose from are: (you may use the abbreviations shown) Identical (I) enantiomers (E) diastereomers (D) none of these (N) H OH OH OH H OH I I H H OH OH c9996? Molecule of the Day . Match the molecules shown below with the statements. (14 pts) A greasy antiviral. . Scotchgard in the arctic! ____ __ Flaming ice cubes. Spearmint or caraway. Let your chiral nose tell the difference. 0. Sphegodus wears a tantalizing perfume. It is called BEEWARE. A little bit of a Jeckel and Hyde molecule. It helps save humans and helps destroy birds. . Get some of this molecule on you and you are in for a chilling experience.____ (ii A . I C] 021-029 alkanes/alkenes menthol A B carvone D CF8(CF2)7503H CH4 (H20)n perfluorooctanoyl sulfonate F methane hydrate G amantadine E 4. Predict the product(s) from the following reactions. Pay attention to any instructions given in the boxes. (48 pts) the major product all possible products including stereoisomers the major product 1. LiA|H4 ——®—’ 2. H30 continued on next page 'Jl \ ~ \ ~ the major product all possible monofluoronated products including stereoisomers (-1pt for each identical structure drawn) 5. Write logical arrow-pushing mechanisms for the following reactions. (45 pts) MOH + HBr ——> )WBr + H20 W 9 9 Ho O_ —» + Ho—§—CH3 §— CH 3 heat 0 0 Continued on next page I? MeOH H '9. + Ho—fi'-CH3 ————> M + HO—§‘CH3 0 '0 YOU WILL NOT NEED ALL THIS SPACE. I JUST DIDN’T WANT TO START THE NEXT PROBLEM ON THIS PAGE. Above and Beyond? 6. 27 pts A. Reaction of the following two optically pure compounds led to a SINGLE product that was OPTICALLY lNACTlVE. Show the product and EXPLAIN WHY it is optically inactive. B. Starting with any ACHIFlAL substituted cyclohexane of your choice design an experiment that would allow you to determine if the 8N2 reaction goes with inversion or retention of configuration. Be sure to show all of your starting materials. Also show and label the products you would expect to obtain if the reaction went with inversion or retention of stereochemistry. C. Write logical arrow-pushing mechanisms that account for formation of the _ following products. NOTE: The two products shown are not the only ones formed in this reaction. However, they are the only ones you have to account for in your mechanism. 6) (9 (9 e 69 G) \ - Br \ - \ - Br A/ - H NMe2 N8. Br - 2 _—> H + ©/\/ heat “One of fifi’s quiet excitements is to stamfsomewfiat ayartfiom yoursefiand'watcfi yoursefi‘softfy Eecoming the author ofsometfiing Eeautifuf, even it is onfy a floating ash.” Norman Mac/e471, 521 River Runs Tflrauflfi 7t 10 ...
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This note was uploaded on 02/16/2010 for the course CHEM 3A taught by Professor Frechet during the Spring '10 term at UC Davis.

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fall02-mt2-Pedersen-exam - Dr. Steven Pedersen November 4,...

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