Test 2 with Answer Key for Organic Chemistry II | CHEM 3020, Exams of Organic Chemistry

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108 pts Name. ke / 3/z1)20\r 8 CHEM 3020 Test 2, Ch. (19-22), March 17, 2011 Show work for partial credit, You may use the periodic table and other information provided. Read the questions carefully. Good Luck! Part I. The Brain Warm-up , 1, Provide the IUPAC name (3 pts) Provide the structure (3 pts) ° {canis suyn low ° ° ' a N . & pow ont & ee «oie aci a BOYS b, (2R)-2-bromopentanedioic acid Baethyl- 2--mahry| aydloharan ane 2. Rank the following according to increasing acidity (your #3 is most acidic) (3 pts). ° ee 9 one ° consider Gc om BO Jk pe AY cory base. H~ ~OH HgC” ~OH CIC” “OH 7 2 x7 | “3 eto? ee. sted Wee, 3. Circle the structure likely to have 'H NMR sj um with a doublet at 5 10.5 ppm. (3 pts) oO os ° s 9 “ © Sug on > ‘OH en 2 gle DN Ys er Yee Leet I Xone selsting i ter GN heave isopopy\ (segtet) = miydd peter sels 4. Circle TWO possible starting materials for synthesis of an enamine. (4 pts) HgC.. Hs Hee, g q CHg HC HOCH Hg” ~OH 3° {2 ewaldayd, acid 5. Circle the carboxylic acid derivative that reacts fastest with hydroxide ion, OH *. (3 pts) i g HyC"°*OCH, Hy0"ONHp ° 8 uot S 4 atu > atodée >» ator » Reva, 6. Circle the reagent that increases reactivity of carboxylic acids to form e.g. amides. (3 pts) PCC CBS (0c) omc / “ J 4 ox neds dutydation coroony x Cahanyls adds > estes or amido woe MAA, NALD