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Assignment_3_2011_Answers - b 2-butanol c 2-methylpentane d...

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CHM 1321 Assignment 3 - ANSWERS 1) Identify each of the following pairs as constitutional isomers, stereoisomers (configurational isomers), or conformers. 2) Draw each structure below along with its mirror image. Indicate whether the compound is chiral or achiral. a) cis -1,2-dimethylcyclopentane. b) trans -1,2-dimethylcyclopentane c) cis -1,3-dimethylcyclohexane d) trans -1,3-dimethylcyclohexane Assignment 3 - Answers 2 Question 2 cont’d: g) CH 3 CClBrH h) (CH 3 ) 2 CHOH i) CH 3 CH 2 CHOHCH 3 j)CH 3 CH 2 CHOHCH 2 CH 3 3) Identify the chiral centres in the following molecules: (indicated with a * ) a. fexofenadine (Allegra): b. Indinavir (Crixivan):
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Assignment 3 - Answers 3 4) Draw each of the following compounds in three dimensions. Draw the mirror image of each and determine whether the compounds are chiral. For all chiral compounds, determine whether the configuration of each stereogenic centre is R or S. a) 1,3-dibromobutane
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Unformatted text preview: b) 2-butanol c) 2-methylpentane d) 3-methylpentane e) 3-methylhexane f) 1,2-dihydroxypropane g) 1, 2, 4-trihydroxybutane 5) For the following compounds, show the stereogenic center(s) by labeling them with a star (*) and determine the configuration of each centre (R or S). Assignment 3 - Answers 4 6) Phenylalanine has the following structure, given that the configuration is S, what is the proper way to draw the compound? 7) Give the stereochemical relationship between each pair of isomers (enantiomers, diastereomers, meso compounds). USE A MODEL! a. Same compound b. Enantiomers c. Same compound d. Diastereomers e. Enantiomers f. Enantiomers 8) Which of the following pairs of compounds could be separated by a method such as distillation or recrystallization? Enantiomers (cyclohexanes) – not separable Diastereomers (salts) – separable...
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