TEST 4_CEB Summer 2015.pdf

2 plausible resonance structures 6 pts 14 provide the

Info icon This preview shows pages 5–7. Sign up to view the full content.

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
Image of page 5

Info icon This preview has intentionally blurred sections. Sign up to view the full version.

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?
Image of page 6
Image of page 7
This is the end of the preview. Sign up to access the rest of the document.

{[ snackBarMessage ]}

What students are saying

  • Left Quote Icon

    As a current student on this bumpy collegiate pathway, I stumbled upon Course Hero, where I can find study resources for nearly all my courses, get online help from tutors 24/7, and even share my old projects, papers, and lecture notes with other students.

    Student Picture

    Kiran Temple University Fox School of Business ‘17, Course Hero Intern

  • Left Quote Icon

    I cannot even describe how much Course Hero helped me this summer. It’s truly become something I can always rely on and help me. In the end, I was not only able to survive summer classes, but I was able to thrive thanks to Course Hero.

    Student Picture

    Dana University of Pennsylvania ‘17, Course Hero Intern

  • Left Quote Icon

    The ability to access any university’s resources through Course Hero proved invaluable in my case. I was behind on Tulane coursework and actually used UCLA’s materials to help me move forward and get everything together on time.

    Student Picture

    Jill Tulane University ‘16, Course Hero Intern