Exam210A_answers - Exam # 2A Chemistry 2401 November 4,...

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Exam # 2A Chemistry 2401 – November 4, 2010 (12) I. Name each of the following compounds. Include the stereochemical designation (R,S or cis,trans) for each of the examples where this is appropriate. A. B. C. C Cl H CH 2 CH 3 CH CH 3 CH 3 CH 3 CH 3 H H Br H cyclopentyl bromide or R-3-chloro-2-methylpentane trans-1,2-dimethyl cyclohexane bromo cyclopentane (20) II. Draw structural formulas for each of the following. CH 3 H H CH 3 OH AgNO 3 CH 3 H OCH 3 H A. The initial carbocation intermediate formed B. The second carbocation intermediate formed in the reaction shown above. in the reaction shown above. CH 3 H H CH 3 H H Shown at the right is 2R-bromo-5R-methoxyhexane. C. Draw a structural formula for an enantiomer D. Draw a structural formula for an diasteromer of 2R-bromo-5R-methoxyhexane. of 2R-bromo-5R-methoxyhexane. H H CH 3 O Br H OCH 3 H Br H H CH 3 O Br OR E. Of the two structures you drew in parts C and D, which of those compounds would rotate the plane of polarized light. Since C and D are both chiral they will both rotate the plane of polarized light. OCH 3 Br H H
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(6)III. For each of the following sets of three groups, circle the one that has the largest Cahn-Ingold- Prelog priority and underline the one with the lowest priority. C OCH 3 O O C O CH 3 NH C O CH 3 C CH CH CH 2 C CH 3 CH 3 CH 3 (10) IV. Consider the dehydration of 1-cyclopentylethanol shown below. C CH 3 CH 3 CH 3 CH CH 2 H + A B C H 2 O H + C CH 3 CH 3 CH CH 3 CH 3 OH slow At the right are structural formulas for the three intermediates. A _____________ B _____________ In the space at the right, sketch the
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This note was uploaded on 03/06/2012 for the course CHEMISTRY 90262 taught by Professor Mccord during the Spring '09 term at University of Central Arkansas.

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Exam210A_answers - Exam # 2A Chemistry 2401 November 4,...

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