TEST 4_CEB Summer 2015.pdf

2 plausible resonance structures 6 pts 14 provide the

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2 plausible resonance structures (6 pts) 14) Provide the best reagents for the following transformations. In some cases, there may be more than one correct answer. (12 pts; 2 pts ea) 1,3-cyclohexadione O O O OH O Cl O Cl O N H O OH CH 3 O OH OH OH Br CN NH 2 1. NaBH 4 2. H 3 O + 1. NH 3 2. NaBH 4 H 3 O + , Δ SOCl 2 NaOH, H 2 O PBr 3 CH 3 CH 2 NH 2 (2 equivalents) NH 3 (2 equivalents) CH 3 OH, base Mg AgNO 3 , NaOH (Tollens’) PCC H 3 O + Br 2 , CH 3 CO 2 H 1. CH 3 MgBr 2. H 3 O + 1. LiAlH 4 2. H 3 O + or H 2 O CrO 3 H 2 SO 4 or H 3 PO 4 , Δ m CPBA NaCN Cl 2 , FeCl 3 CH 3 C(O)OC(O)CH 3 NaSH Na + SCH 2 CH 3 I 2 , H 2 O H 2 , Lindlar catalyst HI TFA (CF 3 CO 2 H) H 2 , garbage bag, Mg, a match CO 2 (dry ice) N O O OCH 3 O H 3 C Cocaine a b c d e N S H N CO 2 H O O Amoxicillin NH 2 HO
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15) Complete the chair conformation by drawing the lowest energy conformation of the following stereoisomer of 1,3,5, trimethylcyclohexane. You do not need to show the hydrogen atoms on the cyclohexane ring. (5 pts) 16) Draw the chemical structures in the boxes to complete this synthetic sequence (6 pts) Multiple Choice . (4 pts) 17) ______ What is the relationship between the following compounds? a) enantiomers b) diastereomers c) identical d) meso 18) ______ Which of the following compounds are optically active?
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