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assignment 3 answers - CHM 1321A Assignment 3 Answers 1...

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CHM 1321A Assignment 3 Answers 1) Draw each structure below along with it’s mirror image. Indicate whether the compound is chiral or achiral. a) cis -1,2-dimethylcyclopentane. b) trans -1,2-dimethylcyclopentane CH 3 CH 3 H 3 C H 3 C Achiral - mirror images are superimposable (meso compound) a) CH 3 CH 3 H 3 C H 3 C Chiral - mirror images are not superimposable b) c) cis -1,3-dimethylcyclohexane d) trans -1,3-dimethylcyclohexane Achiral - mirror images are superimposable (meso compound) c) Chiral - mirror images are not superimposable d) CH 3 CH 3 H 3 C CH 3 CH 3 CH 3 H 3 C CH 3 O e) O O f) O Achiral - mirror images are superimposable - no stereogenic centre, 2 identical groups on tetrasubstituted carbon O O Chiral - mirror images are not superimposable 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 Cl Br Cl Br g) Chiral - mirror images not superimposable h) OH HO Achiral - mirror images superimposable (2 identical groups on central carbon) i) OH OH Chiral - mirror images not superimposable OH OH j) Achiral - mirror images superimposable (2 identical groups on central carbon) 2) Draw the enantiomers of the following compounds and determine whether they are chiral. For all chiral compounds, determine whether each compound is R or S. a) 1,3-dibromobutane b) 2-butanol c) 2-methylpentane d) 3-methylpentane e) 3-methylhexane f) 1,2-dihydroxypropane g) 1, 2, 4-trihydroxybutane a) Br Br Br Br Chiral R S b) OH OH R S Chiral c) Achiral d) Achiral e) Chiral S R f) OH HO Chiral OH OH R S g) OH HO Chiral OH OH R S HO OH (Priorities in red) 1 2 3 3 2 1 1 1 2 2 3 3 1 1 2 2 3 3 1 1 1 1 2 2 2 2 3 3 3 3
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