spring11sampleexam3blank

spring11sampleexam3blank - 1) CH 3 COCH 2 Cl 2) neutralize...

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1 322b Practice Third Progress Test Spring 2011 Chapters Solomon (17),18-19. 1. Circle and give the most accurate names of the functional groups. NH O CH=O NEt 2 O O O OR C O OR RO C O CHCO 2 CH 3 H 3 C CH 3 C OH C H 3 C CH 3 CCH 3 O CH 2 (CO 2 Et) 2 C 3 H 7 NCO O O O NH O O O O O 2. Arrange in order of Brønsted acidity starting with the most acidic compound. (a) ( b ) (c) (d) (e) RCONH 2 (CH 3 CO) 2 CH 2 CH 3 CO 2 C 2 H 5 RCO 2 H O OEt O 3. Arrange in order of decreasing basicity: CH(CO 2 Et) 2 CH 2 CO 2 Et CH 2 COCH 3 CH 2 CON(CH 3 ) 2 CH(COCH 3 ) 2 (a) (b) (c) (d) (e) 4. Write all resonance structures of: C O NH - H 3 C a. C OH NH 2 H 2 N b. c. Ar(CO)NH - 5. Write the mechanisms including all intermediates (no resonance structures or transition states please) curved arrows and formal charges if applicable. a CN H 3 O + heat CO 2 H
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2 c CHO + CH 3 CO 2 Et EtONa/EtOH CH=CHCO 2 Et + H 2 O b. C CH 3 O + H 2 13 CO + Et 2 NH C CH 2 13 CH 2 NEt 2 O + H 2 O HCl 6. Give the predominant products if no reaction occurs. Write: “no rxn”.
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Unformatted text preview: 1) CH 3 COCH 2 Cl 2) neutralize a. c. CO 2 Et + O O 1)EtONa/EtOH b. O OH O 100 C d. N CO 2 Et + CH 3 CO 2 Et excess EtONa/EtOH 2) H 3 O + no acid workup. e C O CH 3 2) BrCH 2 1) EtONa/EtOH 3) OH 4) H 3 O + heat CH 3 COCH 2 CO 2 Et 3 1) LDA h. f. Br 2.) OH + CH 2 O + HCl i. NH j. CO 2 H heat k. CO 2 H l. O N H "one pot reaction" + CO 2 g. N + CH 2 =CHCN C 2 H 5 OH O + OEt O EtONa/EtOH EtO 2 C(CH 2 ) 4 CO 2 Et 1. EtONa O H 2. H 3 O + 4 7. Give equations describing the synthesis of: a. using the aceto acetic ester method. O b. c. CCH 2 CH 2 NHC 2 H 5 using O and any other needed reagent. OH CH 2 NH 2 from O and any other reagent(s)....
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This note was uploaded on 03/15/2012 for the course CHEM 322BL taught by Professor Singer during the Spring '07 term at USC.

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spring11sampleexam3blank - 1) CH 3 COCH 2 Cl 2) neutralize...

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