Exam_1_Answer_Key - I(9 pts Provide structures or names for...

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Unformatted text preview: I. (9 pts) Provide structures or names for the followirlg compounds (A, B, C). (A) Cis-Z-melhyl—l-propylcyclohexane “~9ch flue 3&st ‘H Corredl wad‘lm‘; :2, 3- W" .“ (C) law - 2. (9 pts) Label the functional groups in the following Structures. ‘4" I ( ic'c + I 4% r em u PC, R+%+Q —9+'5 Bra-aflls A'YB *3‘3 ’D-t-B-i-C. -9+'-3 E++ulg A-l-C Aroa-HIS A*D*E_fiilg 4%an oQF-Rscmiss‘mffixmx c as W - (oi—b3 PO'M’TS 3. (10 pts) Draw all major resonance structures for the following molecules. Q93)" JED; SWE- 4. (12 pts) Penicillin has the base structure shown (R: carbon based fragment) and was first synthesized at MIT by the late Professor Sheehan. Circle the stereogenic carbons and indicate their absolute stereOChemistry. 5. (12 pts) Sketch out the orbitals for the following compounds indicating all of the respective orbital hybridizations as p, 3, sp, spz, or Sp3 for every chemical bond. 6' OH CHa H OH 22 IL 32 \0/ \C/ \OH H30 H2 _ . H2 N02 af‘e Lars, r— m... 0 H Kesoflaiff’ H O ‘ — dub ‘w‘ OH OH DAG H ,wéuE/JYWC Hz 0H cada- 7. (7 pts) The diagram shown below describes a particular chemical reaction. Answer the following questions using this plot. (a) How many transition states are present along the reaction pathway A 9 D? 3 (b) How many intermediates lie between A and D? Q (c) Which reaction of intermediate B is faster? B 9 C or I ((1) Which compound (A, B, C,or D) is present in greatest amount at equilibrium? (6) Which compound (A, B, C, or D) is present in least amount at equilbrium? I (f) Is the reaction exothermic 0r endothermic? €\< El" UM» ‘L (g) Which step is the rate determining step? A 9 B, B 9 C or C 9 D (circle one) 9 a (circle one) let“ ea,de 0 § c d) E B g A D progress of the reaction 8. (4 pts) Rank the following in terms of their relative strength as a Bransted base (1: strongest base). H30 \ N A 3 \ Q l | a a 29“ 3?}; 6mat=l r drier 10. (16 pts) Draw the two chair conformations of the following molecule. Circle the most stable conformation. Draw a Newman projection of both confmmations when viewed down the axes indicated. 11. (8 pts) Draw curved arrows and place formal charges where appropriate in the following two reactions. +4945 1/ at +4638?“ ' .. — r H F kOH ii...ng + 39—;- >+— + H20 + B —l- Br b. N H ’6“ \ arqu ‘“ m each. rm Q m. . 09,019 on \ Hay—(I: + PH it Hag—F '+ 4 8%“ W0 U3“ \ 4‘ '— lFFoFMxl (has; 5 M‘xSS‘iKa \ Affine, MRSO‘CRli C, 3,. arc—cum mam fv Extra Credit (3 points) Draw the most stable conformer of 1,4—cis—di(tert-butyl)cyclohexane. ...
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