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ex02anss2012 - MCMP 204 Exam 2 Spring 2012 ANSWERS Page 1...

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MCMP 204 / Exam 2 / Spring 2012 ANSWERS Page 1 Examination 2 with Answers The questions marked with an asterisk (*) is from the discussion portion of the exam. Potentially useful constants: 2.3 RT at 298 K (25 °C) = 5.71 kJ mol –1 ; h (Planck’s constant) = 3.99 × 10 –13 kJ s mol –1 1. (8 points) Provide an IUPAC name for the following compound. Include stereochemical designations. 2. (23 points) (a) (4 pts) Circle the number next to the ONE correct statement; or, if they are all correct, circle the last choice. The separation of a racemate into enantiomers requires— (1) a compound that can form a salt with the racemate. (2) the interaction of an enantiomerically pure chiral substance with the two components of the racemate. (3) a solvent from which the salts formed from the racemate can be crystallized. (4) all of the above. (b) (5 pts) Consider the following two structures. Structures A and B are (circle ONE)— (1) enantiomeric conformations of the same compound. (2) diastereomeric conformations of the same compound. (3) enantiomers but not conformational isomers. (4) diastereomers but not conformational isomers. (5) none of the above. C C H 3 C Et H C CH 2 CH 2 CH 3 H CH 2 OH ( R,Z )-4-methyl-2-propyl-3-hexene-1-ol or ( R,Z )-4-methyl-2-propylhex-3-ene-1-ol CH 3 H 3 C CH 3 CH 3 CH 3 H 3 C CH 3 CH 3 A B
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MCMP 204 / Exam 2 / Spring 2012 ANSWERS Page 2 (c) (4 pts) A typical carbon–carbon double bond stretching vibration absorbs infrared radiation at about 1650 cm –1 . The absorption frequency of a carbon–carbon triple bond should be at about (circle ONE)— (1) 4950 cm –1 (2) 2475 cm –1 (3) 2020 cm –1 (4) 1800 cm –1 (5) 1352 cm –1 Comment: We expect this to follow the square root of the relative bond strengths, i.e., (3/2) (d) (4 pts) The stretching vibration of a carbonyl group absorbs infrared radiation at about 1700 cm –1 . What is the energy of this radiation, in kJ mol –1 ? Show your work. (e) (4 pts) Circle the compounds below that, when dissolved and analyzed at room temperature, will produce a solution that gives an optical rotation measured by a polarimeter. (f) (6 pts) The alkene ( Z )-2-hexene adds Br 2 to give (circle ONE)— (1) (2 S ,3 R )-2,3-dibromohexane (2) equal amounts of (2 S ,3 R )-2,3-dibromohexane and (2 R ,3 S )-2,3-dibromohexane (3) mostly (2 R ,3 R )-2,3-dibromohexane (4) mostly (2 S ,3 S )-2,3-dibromohexane (5) equal amounts of (2 S ,3 S )-2,3-dibromohexane and (2 R
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ex02anss2012 - MCMP 204 Exam 2 Spring 2012 ANSWERS Page 1...

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