spring11sampleexam4blank - 2 OH O O H 6 Give the...

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1 322b Practice Third Progress Test Spring 2011, Chapters Solomon 20-22. 1. Write the structure (choose your own example) a. Ester b. Lactam c. Oxime d. Sulfonamide e. Thioacetal f. Osazone g. Imide h. Carbamate i. Dialkyl carbonate 2 . Circle the most (M) and least(L) stronger Brønsted acid : RSO 2 NR 2 RSO 2 NHR' ( ) ( ) ( ) ( ) ( ) RCONH 2 NH 2 NH 3. Arrange in order of decreasing basicity: 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 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 N Bu + LiH b. Br ONa + O BuLi OH -
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2 c. f. O O OH +CH 3 CO 2 H HC(O)(CHOH) 3 CH 2 OH OH - H 2 O HC(O)CH 2 OH + HC(O)CHOHCH
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Unformatted text preview: 2 OH O O H 6. Give the predominant products if no reaction occurs. Write: “no rxn”. a. NH HCl/NaNO 2 b. N 2 + , Cl + KI c. EtNHC S N O O O short reaction time H 3 O + d CCH 3 + CH 3 NH 2 O H 2 /Ni e. N 2 , Cl + CH 3 O NO 2 g. N CH 3 CH 3 1) CH 3 Br 2) Ag 2 O, f. CH 2-C-NH 2 O Br 2 /OH-3 i. O Br CO 2 H Na/CH 3 OH O O j. k. O O 2 N N 2 + ,Cl-NaOH ∆ ∆ 7. Synthesize Starting with OH OH OH O Starting with benzene and any other needed reagent synthesize : O CH 3 CO 2 CH 3 Starting with OH and synthesize: O 13 CH 2 CH=CH 2 CH 2 CH= 13 CH 2 and using any other needed reagent CH 2 OH OH OH OH O CH 2 OCH 3 Br 13 CH 2 CH=CH 2 b c a....
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