1 CHM 1321 C Midterm 1 - Université d'Ottawa

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14.a. Draw the two chair conformations of trans-1-tert-butyl-2-ethylcyclohexane. (5 points)b. For each structure, label the substituents as being axial or equatorial. (2points) – 1 per errorc. Identify the most stable and least stable conformation. (1 point)/5:1 point: chairs well-drawn1 point: right molecule1 point: both conformations drawn (many people drew the enantiomer)2 points: orientation of the substituentsaxialaxialequatorialequatorialleast stablemost stable115. Consider the Newman projection of propan-1-ol down the C1-C2 bond.OHa. Draw and name the Newman projection of the least stable conformation (3points)HO CH 3HH HHeclipsed1 required conformation1 correct molecule1 name of conformationb. Draw and name the Newman projection of the most stable conformation(3 points)HHCH 3HHOHanti1 required conformation1 correct molecule1 name of conformation5

16. Ephedrine has the structure shown below but with the (1R, 2S) configuration.a. Draw its structure with the correct configurations at the stereocentres. Thepriorities given to each group to determine the correct structure must beindicated (redrawing the structure for each chiral centre helps). (4 points)b. Draw the enantiomer of ephedrine. (2 points)a. 1 point per chiral centre drawn with correct stereochemistry2 points for the priorities being correctly assignedOHHN14OHHHOH3R 2HNCH 3CH2 S 334 H HN1 CH 3b.OHCH 3HN2 points (- 1 per error)BONUS!Is the following molecule chiral? Explain or show clearly how you came to thatconclusion (2 points)HH 3 CClC C CHClCH1CCHCH 3YES, because the molecule is not superimposable on its mirrorimage.1ORYES, because the molecule does not contain a plane of symmetry (with justification)6