Exam2gilbertkey - [26 1 The following questions require that you provide the structure of an organic compound which you may write using zig-zag

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2 [26] 1. The following questions require that you provide the structure of an organic compound, which you may write using “zig-zag” representations if appropriate. You are also asked to provide other information in each question, so don’t forget to read the question carefully! (6) a. Write the structure of 1,3,6,6-tetramethyl-1-cyclohexene and with an asterisk (*) specify stereocenter(s), if any, that you can identify in it. * (6) b. Write the structure of a cyclopropane of molecular formula C 6 H 12 that is a meso isomer. Define the term, “ meso isomer.” A meso isomer is a configurational isomer having two or more stereocenters and a superimposable mirror image. or A meso isomer is a configurational isomer having two or more stereocenters and a mirror plane of symmetry. (6) c. Write the structure of an acyclic alkene of molecular formula C 6 H 10 Br 2 that cannot be a diastereomer ( E or Z isomer) but contains a single stereocenter. Define the term, “diastereomers.” Br Br Br Br Br Br Br Br Diastereomers are configurational isomers that are not enantiomers. (6) d. Using wedges and slashes as needed, write a three-dimensional representation of the R enantiomer of the molecule shown below. Be certain to specify the group priorities that you assign. Define the term, “enantiomer.” C Br C H 3 C H C CH 2 H 3 C C H 2 C H H 1 2 3 4 C Br C H 3 C H C CH 2 H 3 C C H 2 C H H R An enantiomer is a stereoisomer having a non-superimposable mirror image.
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3 [20] 2. The following questions test your understanding of potential energy diagrams. (10)a. In the space provided , create a potential energy diagram that meets criteria shown on the equation below; the enthalpies are in kcal/mol. Note (1) that the values of the heats of reaction, H rxn , for formation of the products D and E of the reaction are –14 kcal/mol for formation of D and –18 kcal/mol for formation of E and (2) that B and C are both reactive intermediates, C being the more stable of the two . Label the axes of your diagram and with
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This note was uploaded on 02/18/2010 for the course CHEMISTRY 310N taught by Professor Gilbert during the Summer '08 term at North Texas.

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Exam2gilbertkey - [26 1 The following questions require that you provide the structure of an organic compound which you may write using zig-zag

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