ps3 - CH 3 H 3 C CH 3 H H CH CH 2 CH 3 H CH 2 CH 3 CH 3 CH...

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Chemistry 3590 Organic Chemistry I PROBLEM SET #3 FALL, 2009 Please answer problems 18, 36, 38 and 39 in Chapter 3 of Bruice. Also answer the following questions: (1) Calculate the degree of unsaturation in Plavix, whose formula is C 16 H 16 ClNO 2 S. Then, indicate where each unit of unsaturation is located in the molecular structure, which was discussed in class. (2) For each of the following structures draw a Newman projection that best depicts the most stable conformation of each molecule. (a) CH 3 CH 2 CH 2 Br (c) CH 2 =CH–(CH 2 ) 2 OCH 3 (b) Cl(CH 2 ) 4 Cl (d) (CH 3 ) 2 CHCH 2 CO 2 H (3) Shown below are three Newman projections A-C . Which, if any, are identical compounds? CH 3 H CH 3 CH 3 CH 2
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Unformatted text preview: CH 3 H 3 C CH 3 H H CH CH 2 CH 3 H CH 2 CH 3 CH 3 CH 2 H CH 3 CH 3 H H 3 C CH 3 A B C (4) Using the curved arrow formalism, propose a mechanism for the following alkene addition reaction, which uses an acid catalyst. + CH 3 SH catalytic H 2 SO 4 SCH 3 (5) An interesting isomerization takes place when one attempts the addition reaction of HCl to the alkene shown below. Use the curved arrow formalism to propose a plausible mechanism for this reaction. Also, indicate the correct IUPAC name for the reactant and product shown, and include the ( E ) or ( Z ) designation where appropriate. CH 2 H CH 3 CH 3 H 3 C + HCl H 3 C CH 3 CH 3 H 3 C...
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