Exam+1+--+Fall+2006+--+ANSWERS+_do+not+distribute_-1 - Name...

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Name _______________________ Page 1 I. (20 points) A. This year marks the 100th birthday of pharamaceutical chemist Albert Hofman, inventor of LSD. To recognize the occasion, consider the structure of LSD below, and answer the questions about this drug's structure and reactivity (as usual, you should consider other closed shell resonance contributors in your evaluations). N H N C H O N C CH 3 C CH 3 H H H H CH 3 LSD (lysergic acid diethylamide) ATOM O (a) For each of the atoms indicated with an arrow, provide the atom's most reasonable hybridization as well as its electronic geometry (VSEPR), and observable geometry (shape). no partial credit Observable geometry ATOM N1 ATOM N2 ATOM C ATOM O ATOM C ATOM N1 ATOM N2 sp2 sp3 sp2 sp3 none tetrahedral trigonal pyramid trig planar (b) How many units of unsaturation does LSD have? (c) LSD is absorbed easily into the bloodstream in this neutral form. However, it is ultimately protonated is the process of breaking it down. Circle the most basic site in the structure of LSD. 2 2 2 2 2 (c) most basic site circled B. Mustard gases are highly toxic, skin-blistering compounds that were developed for use as chemical weapons decades ago. The structure of one of these compounds, the "sulfur mustard," is shown. S C C C H H H H Cl H H C H H Cl (a) Do you expect the sulfur mustard to have a dipole moment? sulfur mustard, C 4 H 8 Cl 2 S S ClH 2 CH 2 C ClH 2 CH 2 C Indicate molecular dipole or circle: None (b) Several structural isomers can be drawn for sulfur mustard, but one contains the most acidic H atom that can be designed using this molecular formula (C 4 H 8 Cl 2 S). no partial credit C C C S Cl Cl H H H C H H H H H pKa <10 4 4 tetrahedral geom must be shown dipole must point generally toward Cls i) Draw a proper 3-D picture that clearly shows location of all electrons (bonded and non-bonded) around the central sulfur atom ( n o other atoms should be shown in 3-D), and ii) indicate the direction of the molecular dipole, or circle "None" ( meaning you expect the dipole moment to be 0) in the box. i)Draw this isomer,keeping all shells
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This note was uploaded on 01/30/2011 for the course CHEM 210 taught by Professor Capolla during the Spring '07 term at University of Michigan.

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Exam+1+--+Fall+2006+--+ANSWERS+_do+not+distribute_-1 - Name...

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