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Exam 1 key - CHEMISTRY 2212 EXAM 1 Be sure to read each...

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Unformatted text preview: CHEMISTRY 2212 EXAM 1 September 14, 2011 Be sure to read each question carefully. Partial credit will be assigned where appropriate. To receive full credit you must answer the question completely. Relax and good luck!! 1. (8 pts) Provide skeletal structures for all of the possible products of the following halohydrin reaction. More boxes than are needed to answer the question correctly have been provided. You do not need to show stereochemist E/Z or R/S} in your answerjslz ' 0 H g“ kc-Bm —Z~ MOLL‘ bonz‘lALk or z—erA7/ — (—(1-~.+«7/ (”P70 wiavkuyk Br Ii: '—‘Lm’\"°"3"".+“0 RAW 'r M- gmr‘woni'h'o bay/u, N02 3. (2 pts) Provide the appropriate skeletal structure for each of the IUPAC names given below: 4-tert—butyl-2-isopropylaniline Name: 4. (10 pts) Label each compound as Aromatic, Anti-Aromatic or Non-Aromatic. Write the appropriate label in the space provided. Mar-w «minds; 5. (5 pts) For the reaction below, provide the missing reagent(s) and/or intermediate(s). Where necessary, be sure your structures clearly indicate the correct stereochemistry. If more than one intermediate would be produced, only draw the structure that leads to the final product (don’t worry about drawing both enantiomers of a racemic mixture). BM} “1", “"1 or 690 or 418A) @ WV rad. “l WJLN'S "he “uh? CH3 (”WW paint“ \[D’ rcSv-H' 40m, “5"in ”II/COCHS bran-int. km Name: 6. (12 pts) Provide the major product(s) resulting from the addition of one equivalent of LI__B__r to the following compound under each of the specific conditions indicated below: ‘1‘ You must provide the structure of each final product as ,. of the specific intermediate that leads to each product. You do not need to show stereochemist E/Z or R/S} in your answergsl. Reaction carried out at 0° C, short reaction time Intermediates Products Reaction carried out at 40° C, long reaction time Intermediates Products Name: “a 7. (12 pts) Complete the following Diels-Alder reaction schemes by providing either the appropriate diene/dienophile starting materials or all possible reaction product(s). Show specific stereochemistry when appropriate: 5?: (,.r(,,.§ art Ao,’ ¢L..’r«.\ (no 3454 I or “(<1ny CH3 IHK + I ' Heat ———_> 00201ch3 Name: M 8. (8 pts) Provide all of the possible resonance structures for the charged, p-nitro intermediate of the following reaction. question correctly have been provided: More boxes than are needed to answer the ____.._______—__..—__———.___ 9. (11 pts) Using curved arrow formalism, reaction. Show the mechanism for in-si Name: M show the step-wise mechanism for the following tu formation of the electrophile in the appropriate box and the overall reaction mechanism in the other space provided. In your overall reaction mechanism, you do not need to show all resonance forms of the reaction intermediate. shown below undergoes polym Radical Catalyzed Polymerization ——‘__> Acid Catalyzed Polymerization erization via 1,4-addition: gment of the polymer formed when the con' Name: a“ 12. (14 pts) Complete the followin and/or all major producqsl: g reaction schemes by providing the appropriate reagent(s) CHO Monosubstitution AICI3 Monosubstitution E: A Q .___._____———_— 02N H2, Pd/C “a EtOH, 1 atm 11 ...
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