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PracticeExam(key) - Kmar. Chemistry 334 Exam 1 Sprin 201 1...

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Unformatted text preview: Kmar. Chemistry 334 Exam 1 Sprin 201 1 1) (32 points) Fill in the blanks. Draw all major products. (Note: some reactions may require more than one set of reagents). o H _ , o I...“ l C- H . ‘ --‘!'. O A) «W3 -5 - brwpww NBS. ROOR : light B) C) 97909" ‘48. e‘ fir—9“ t I Q Y‘l.‘ obj-cf) ) O GDWOV-FLO E 1. 03 \V 2. 0) Chemistry 334 2. NaOEtl HOEt E " 3% 1:.) E) ‘ F) 9) Chemistry 334 Exam 1 Spring 2011 2) Comparing stabilities. Short answers: jam? 30 2 '20 7 1° 70mg,” 5W a) (4 points) Circle the most stable radical and gut a box around the least stable radical; Mo . - 5 as?“ ‘i—-—---—- 1 ‘ fl 3% " i J- b) l6 points) Circle the molecules that are aromatic. Put a box around the molecules that are antiaromatic. w s iTe‘ I’ft ro m avail A “Ha-mum‘ab- o c) (10 points) Compare the two carbocations. Use curved arrows to draw the contributing resonance structures. to e * get/m 9‘ / .1 / J. g 1. WU“... Q a, as“ as C c. :.;. a ’ 1 Fa F3 e; 4.32% i a: @ Fat '5 (2. =5“ 3 ‘ a” 14"“? a“? ‘f\~/ _.-d \ :1 Which carbocation is more stable 1 or 2? 0'5 Chemistry 334 Exam 1 Spring 2011 3) (18 points) Circle the diene that reacts the fastest in the following Diets-Alder Reaction. Cross out any diene that wlll not react in a Diels—Alder Reaction. 0 _ 30 0C Dials-Alder Dzene + 0 —"" adduct N02 - .0 No; | [:> i311)? . (M can 9w 1. \ v u: ‘r 1 4A 5' FEW- “men-r D E F 'Hua‘l _-': «tom :- FLU-r" . ‘ ant-EJJ G'KL‘. haw \'t\ I bth 1;: Ii‘f _ _ _ ' I v; I b) Circle the reactant that will react thecfa'ejt’est’) in an Electrophlllgfiiarnatic SubstitutiiSh 54 ‘0‘" A i. (EAS) reaction. Cross-out the reactant that will react slowest. cufigmumtm... o ‘c EQS ma: 3“ . kw o"K 2 inc/- e; rack buirgggofi“ ' 0) Circle the reactant that will react the astest in an EAS reaction. Cross-out the reactant that will react slowest. ‘ product Own?" A a G ?W=‘~‘*-°‘-' Chemistry 334 Exam 1 Spring 2011 4) (20 points) Draw a complete mechanism for the following reactions. Show resonance structures for intermediates stabilized by resonance. (To get complete credit, draw ALL arrows to represent the movement of electrons.) HN03. H250... 0N0: 0 I .. \x a) O H20 9 grog O “ l -\ E“ " + 0 _} .'. {O 5“ ‘ W '0‘ \t to l Ail-9‘:be ii" 0 ttq © ‘5? (3 O \\ ____, M & .._,--/ ______.. l‘ \\ A}: O'SFQA- ’ r/®b?\iri‘ J \‘ .. _ _—\ O k 0 (‘9 /N““O-‘Pf \n \ ED * , ' O ' ' 0 r" a}... r 2 Q5) emit; emcee-r i: A ’0 ‘ g G; u 1%. “M1 92 1| JUL 49‘:- -. -—~ «36? R1953 s“ x...» w I “q no! “"’ a} 5 (3...??u'khijll. ’HQMW Jr 0 $Lfl:é' . ‘55 mews ““‘ fa ” \ "’ or I -. (Tr. K“ bk 8 t‘ E'b.503‘.‘J-f Mechanism continued on next pg. Exam 1 Spring 2011 Chemistry 334 Exam1 Spring 2011 5} (1'5 points) Propose syntheses for the following two transformations. Show all necessary reagents and reactants for each step. (You do not have to show the synthesis of any reagents. if multiple products are formed in a step you need to show them.) EXTRA Synthesis Practice. . ix} \ f, .. (SA "i ii i C.) - 7 7 )Q "’6' Slim 4- ...
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This note was uploaded on 02/20/2012 for the course CHEM 334 taught by Professor Wang during the Spring '09 term at South Carolina.

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PracticeExam(key) - Kmar. Chemistry 334 Exam 1 Sprin 201 1...

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