CHEM 345 SPRING 2017 Final Exam.pdf

3 pts least reactive most reactive slowest fastest 10

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Rank the following compounds in order of their reactivity toward electrophilic aromatic substitution. (3 pts) _______ < _______ < _______ < _______ least reactive most reactive (slowest) (fastest) 10) Draw resonance structures for the carbocation intermediate of the para -chlorination of anisole (8 pts) 11) Draw the most stable chair conformation for the molecule shown below. (3 pts) 12) Multiple Choice . (4 pts) ______ What is the stereochemical relationship between the following compounds? a) enantiomers b) diastereomers c) identical d) meso ______ What is the correct stereochemical configuration for the following drug used to treat asthma? a) R b) S c) E d) Z Cl 2 FeCl 3 OCH 3 anisole OCH 3 Cl H a b c d Br CH 3 NO 2 CH 3 Cl CH 3 Cl CH 3 H 3 C H N OH albuterol H 3 C
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13) Select the best reagents for the following transformations. (22 pts; 2 pts ea) 14) True or False (8 pts) _____ The rate of reaction b is greater than the rate of reaction a . _____ The rate of reactions a & b , but not c , are dependent only upon the concentration of the alkyl halide. _____ Reaction c is an example of a S N 2 reaction. _____ Reaction d is an example of an E1 reaction. O OH OH Cl Br MgBr + (provide a workup step) O OH OH O Br 2 Mg H 2 , Pd/C NaCN Br 2 , CH 3 CO 2 H PCC H 2 , Lindlar catalyst NaSH Br 2 , H 2 O Na 2 Cr 2 O 7 H 2 SO 4 ( or H 3 PO 4 ,) Δ NaC CH Cl 2 , FeCl 3 or Br 2 , FeBr 3 KMnO 4 , H 3 O
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