322B_Spring_09_3RD_PRAC

322B_Spring_09_3RD_PRAC - 2 b. N 2 + , Cl + KI c. CH 2 (CO...

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1 322b Practice Third Prog. Test Spring 2009, Chapters Solomon 18-20 + topic B. 1. Circle and give the most accurate names of the functional groups. C NOH CH 3 CH 3 CH 3 CHCH 2 OH N H O CH=O N 2 + , Cl - NEt 2 O O CH 2 (CO 2 Et) 2 O OR C O OR RO C 3 H 7 NCO C O CHCO 2 CH 3 H 3 C CH 3 C OH C H 3 C CH 3 CCH 3 O C OH O 2. In each of the following pairs, circle the stronger Brønsted acid pair: CH 3 CH 2 CO 2 H or ClCH 2 CH 2 CO 2 H CH 3 COCH 3 or H 2 CO CH 3 COCH 3 or CH 3 CO 2 Et CH 3 CO 2 Et or HCO 2 Et NH 3 or NH 3 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) N NCH 3 NCOCH 3 N(CH 3 ) 2 + NH NH NH (a) (b) (d) (c) (e) 4. Write all resonance structures of: C O NH H 3 C a. C OH NH 2 H 2 N b. c. Ar-N 2 + 5. Write the mechanisms including all intermediates (no resonance structures or transition states please) curved arrows and formal charges if applicable. a. N + CH 2 =CHCN ! C 2 H 5 OH N CH 2 CH 2 CN
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2 c. d. CHO + CH 3 CO 2 Et D EtONa/EtOH CH=CHCO 2 Et + H 2 O b. C CH 3 O + H 2 13 CO + Et 2 NH HCl C CH 2 13 CH 2 NEt 2 O + H 2 O N 2 + ,Cl - H + N N + CH 3 O OCH 3 6. Give the predominant products if no reaction occurs. Write: “no rxn” a. NH HCl/NaNO
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Unformatted text preview: 2 b. N 2 + , Cl + KI c. CH 2 (CO 2 Et) 2 1) EtONa 2) CH 2 Br 3) OH 4) H + , d. Cl CH=O + CH 2 (CO 2 Et) 2 Et 2 NH EtOH e. N 2 , Cl + CH 3 O NO 2 f. S S 1) BuLi 2) PhCH 2 Br H 3 O + g. N CH 3 CH 3 1) CH 3 Br 2) Ag 2 O, h. CCH 3 + CH 3 NH 2 O H 2 /Ni j. EtNHC S N O O O short reaction time i. SO 2 NH H 3 C (one equiv.) H 3 O + Na 2 CO 3 3 k. CH 2-C-NH 2 O Br 2 /OH-l. HO(CH 2 )OH + OCN NCO ( n moles) ( n moles) 7. Give equations describing the synthesis of: a. using the aceto acetic ester method. O b. O 2 N N=N from NH 2 NH 2 as the only carbon source and any other needed reagent. c. O CH 2 CO 2 Et from O and CH 3 CO 2 H and any other needed reagent or compound using enamine chemistry CH 2 CH 2 CO 2 H using CH 2 (CO 2 Et) 2 and any other needed reagents d. CH 3 CCH 2 CH 2...
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This note was uploaded on 10/12/2009 for the course CHEM 322AL taught by Professor Jung during the Spring '07 term at USC.

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322B_Spring_09_3RD_PRAC - 2 b. N 2 + , Cl + KI c. CH 2 (CO...

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