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exam2gilbertkey - [26 1 The following questions require...

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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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