2011SpringExam1

2011SpringExam1 - CHEMISTRY 322bL/325bL FIRST EXAM January...

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Unformatted text preview: CHEMISTRY 322bL/325bL FIRST EXAM January 26, 2011 1 (1-8). ______________ (26) u (9). ______________, (12) 111 (10-15). (34) IV (16). W (16) van. an Total:________________(100) Name: E 3 Section 1. Multiple Choice. (26 points). 1. Circle the compound below that should show the shortest wavelength ultraviolet-visible light absorption. Z 2% a \ ) OF 0 all“: / / / / / ll WV Ill [+ f} S 2. Circle the compound or compounds that are nonaromatic (as opposed to “L aromatic or antiaromatic). Assume that all structures are planar. 1 §3ru9vrc [’3 cm” + ’2 HQ 3311 one 60ch +2 thaw Camel 00/ me Inter/‘er 0 1‘? 4"“0 "ma/"'4 0’! ’4: (of/r54- 0 ,‘F 6/! Lf arc 6”;ch 0 {P 2 Mat/ac} are Ciro/(j Name: E 4 3. Circle the pair of molecular orbitals that are believed to interact in the Diels 4+ *3 4. Circle the electronic configuration or configurations below that correspond __._E-—-— to an aromatic compound. Name: K E 2 5 5. Circle the correct hybridization for the marked atoms in the structure below. P .y M /,‘,«-\6. Circle the structure in which the identified hydrogen has the highest pKa (i.e., 2 the least acidic hydrogen). ‘ .2... Name:__£§Z__ 6 7. Given the transformation below, circle the molecular orbital that w. corresponds to a molecular orbital of the product of this reaction step. 8. Circle the aromatic compound or compounds below. Assume that all structures are planar. only 4m; Carlee} o/‘c alder! w A— ?. ifl on"; one Cor/r61 l3 arc/(J "3‘ ’2' 2 Carrch may I I‘ncofl‘cJ’ O l? anurml- “of I car/4:1 O i? a” 4 ‘m 9"“ Q local/«J- Name: E E 2 7 Section II. Drawing Structures. (12 points). 9. Draw all of the reasonable resonance structures for the compound below. Do not consider charge-separated resonance structures‘ Circle the resonance structure or structures that would be the major contributor to the hybrid. +2 Cut) all 5- Sértcfi/M 3] 6‘4“ (lasfiavf‘ CHELJ ~Q— pdzhtb FOP that) anc’I‘a’ (Arum/‘5 —6 Inc Scficf‘Jfi‘lM Namam 3 Section 111. Complete the Reactions. (34 points). Fill in the reactants, reagents, and /or products for the transformations below. Where appropriate, show the stereochemistry. 10. «74 2,5 / Q pronaB -— '4 P“ (“L ,,. 5306*9L0“ "5 1‘? ("-Cr/vo; InotcoJrj>ficfaj§ 12. 6 fits m” ' ‘ , a , OEt (I + NCTCN “7337‘” + 2 m slow: 1 ‘9"le ~ 3 943 €ch A {(2 nae/w; C05” gmfigv + 2 — Canal reanalmififb \ 3‘0“qu fl no Sac/(aJr/h/So’l‘; p.” “W -\.W_.‘ NameziEL“ 9 3 Pain LS EQGL fix 15. L} CH3 HBr (1 equivalent) D ~-——-—-—-———————* No rear/hm H30 room temperature Name:__L<_E.Z___ 10 Section IV. Draw the Mechanism. (16 points). 16. Draw the "electron-pushing” reaction mechanism for the transformations below. Indicate the structure of the product of step 1 and the structures of the products of step 2. / H C CH \ heat Cl2 Low. Conc. Step 2: Product A 400 °C \ Maven“) 0“ y w \ C)’ V \ 1: -> we» UPC 1" \ "7" r--5....4. \ gym“. waltz) 0/ vs "‘“C ‘6. conémuc 93:36“; ’ m” l /C\ \ f“ w 1‘ qu \ V @M I 1.: K? h 2 if —~Cc . i gm“ 5 d g .’ 7““? f u“, CV“ j: a 1 MN WP ‘. TEIMAoih’m: ' -- o/v') (“Cage/mud —- W \ POI} W Name: K E 2 11 17. Outline an efficient synthesis for the product below using the indicated starting material and any saturated alcohols of 4 carbons or fewer (i.e., methanol. ethanol, both C3H30 alcohols, or any C4H100 alcohols) as the only carbon sources. Consider the major products ofindividual steps for use in subsequent steps. Also, note that stereochemistry is not shown in the product, so it does not need to be considered. Section V. Outline the Synthesis. (12 points). \ ...
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This note was uploaded on 04/02/2011 for the course CHEM 322BL taught by Professor Singer during the Spring '07 term at USC.

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2011SpringExam1 - CHEMISTRY 322bL/325bL FIRST EXAM January...

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