Download 7 Questions of Organic Chemistry 1 - Exam 3 Fall 2007 | CHEM 3311 and more Exams Organic Chemistry in PDF only on Docsity! CHEM 3311-100 Fall 2007 Exam 3 Professor R. Hoenigman I pledge to uphold the CU Honor Code: Signature______________________________________________ Name (printed)____________________________________________________ Last four digits of your student ID number_______________________________ Recitation TA_____________________________________________________ Recitation number, day, and time______________________________________ You have 1.5 hours to complete this exam. No model kits or calculators allowed. Periodic table and scratch paper are attached. DO NOT TURN THIS PAGE UNTIL INSTRUCTED TO DO SO. Recitation Sections: # Day Time TA 111 Monday 8 am Noel 151 Monday 2 pm Noel 191 Monday 5 pm Noel 113 Tuesday 8 am Noel 193 Tuesday 5 pm Noel 112 Wednesday 8 am Doug 152 Wednesday 11 am Jon 192 Wednesday 5 pm Doug 153 Thursday 8 am Noel Page 1 ________/20 Page 4_______/24 Page 2 ________/10 Page 5_______/26 Page 3 ________/20 TOTAL________/100 CHEM 3311, Fall 2007 Exam 3, page 1 of 5 1. (8 pts) One area of pharmaceutical research is the development of hybrid drugs. A hybrid drug is a combination of two drugs into a single compound. Hybrid drugs sometimes have the benefit of being more active than either component drug, and also help treat drug resistant strains of disease. Shown below is a hybrid of quinine and artemisinin, two drugs used to treat malaria. In the boxes below give the stereochemical designator for each indicated chirality center. N H3CO HO N O O O O O O 2. (12 pts) A) In the boxes below draw the indicated compound. B) Based on what we know about nucleophiles and leaving groups, we suspect that the reaction of (R)-2-chlorobutane with sodium iodide in acetone would not be useful as a synthesis of (S)-2-iodobutane. Explain. (R)-2-chlorobutane (S)-2-iodobutane CHEM 3311, Fall 2007 Exam 3, page 4 of 5 6. (24 pts) Give the major organic product(s) of each of the following reactions. If necessary, clearly show the stereochemistry of the products. If no reaction occurs, write NR. Write “meso” under any meso compounds. Note: some problems have more than one step. A. OH CH3H3C HCl B. 1) B2H6 2) H2O2, HO C. (Z)-2-pentene Br2 CCl4 D. O O TsOH2C CH3 CH3 NaI acetone E. (E)-3-methyl-2-hexene Cl2 CH3OH F. 1-bromo-4-methylhexane NaOCH3 CH3OH G. OH TsCl NaN3 CHEM 3311, Fall 2007 Exam 3, page 5 of 5 7. (26 pts) Propose an efficient synthesis for each of the following transformations. You may use any reagents you like. Be sure to show any intermediates. (Do not draw a mechanism.) A. (±)-1-azido-3,4,4-trimethylpentane starting from (R)-2,2,3-trimethylpentane (azido = N3) B. NCCH2CH2CN starting from ethyl alcohol
