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20053-322b_e1 - Chemistry 322b Exam No...

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Unformatted text preview: Chemistry 322b Exam No. 1 September 19, 2005 (1) (20) (2) (5) (3) (35) (4) (10) (5) (10) (5) (20) Total (100) Grader Please Print k2 Last n me First name USC ID Name of TA First letter of last name -/‘ 1. Give the appropriate names or structures for the following questions. Give stereochemistry if relevant Circle the one(s) if UV inactive at 254 nm (5 (p.ts each) \ % £2: 0 “i":zf 53 \vCV' ( g1) -3—Ph9m/LI ,3- pentul‘lene vm' vinil 19642” chlolr‘mle i 1/4 “W K p-bromoaniline NW}, 2. Circle the molecules that are AROMATlC. (5 pts) «3% m % we, / ,2- 3. Predict the major product(s) or provide the proper conditions for the following reactions. lf stereochemistry is involved or there is no reaction, so indicate. (5 pts. each) {225 COzMe NaBH4 OLM — 0\’l , QCHO 732/ W} 61 (”A Br 13 {W m C(Q ¢ JWWC Z MC Q “- If C OHC/VCHO &//¢Mo 2,4 6 «Jam \ V heat :3; ¥ “CH6 LS OH H cc E m Br \Me MAW MezCuLi GY @ o O 2 % ‘0 (14» h ONBr 1. Mg, EtZO Ci \AOKH [001’ . Y/ __ ' HCl,-40°C -3- 4 The following reaction gives two different products. Draw the products in the boxes Then write a reasonable mechanism for each product. (10 pts) is V» (Y, (Mechanism for A) - radical mechanism (Mechanism for B) - ionic mechanism 9/7 9}! «I 6—? gr/KZ/ 5 3V -Lfv 5. Draw both endo and exo products from the following Diels-Alder reaction, and circle which one forms faster. (10 pts) heat COZMe / Q0 E —-+ COgMe 63m @ exo 6. Complete the following syntheses starting with the given molecules. For carbon sources, you may also use any compounds of two or fewer carbons. Do not show mechanisms. Draw structures and write reaction conditions legibly. (10 pts each) 6—1. LAM ow 4’34 arm ‘3 h) L (Hcko (“WWW ) 6-2. / (UL J. \g)’ PCC) Aggy WL M0 o’ -— 5? / tkW 5" \430 OAT __.¢_.§ V‘OA A v on ...
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