Exam 3 with 9 Questions - Organic Chemistry II | CHEM 241, Exams of Organic Chemistry

Download Exam 3 with 9 Questions - Organic Chemistry II | CHEM 241 and more Exams Organic Chemistry in PDF only on Docsity! CHEM 243-Dr. flmmon NHME. Chps. 21-23 Exam 3 flpril 15, 1991 T.fl._ This exam has 9 questions on pages numbered 1-6. Check your copy nouj. Grader 1. ______/1 2 _______ 2. ______/1 5 _______ 3. ______/1 5 _______ 4. ______/23 ________ 5. ______725 __________ 6. ______/24 ________ 7. ______/1 5 ________ 8. ______/1 5 _________ 9. ______/6 _________ Total_____/ISO (12) 1. Which of the following compounds cannot be prepared via an acetoacetic ester synthesis? o o o o a) CH3CCH2Ph b) PhCCH3 c) CH3CH2CCH3 d) CH3CC(CH3)3 (15) 2. Write a complete set of resonance structures for the enolate anion of N=C-CH2-CO2C2H5 . (15) 3. Use cyclopentanone to illustrate the aldol reaction. Show reactants, reagents and products. No mechanisms please. Assume the reaction conditions involve vigorous reflux. (23) 4. Write a detailed mechanism for the following reaction. Show all steps, etc. O CH3CC(CH3)2C02C2H5 - - - (CH3)2CHC02C2H5 + CH3CO2C2H5 EtOH, 25 -1- (15) 7. Starting with 18O-labeled acetic acid as your only source of 18O, show a synthesis of O CH3-CH2-C- 18O-CH2-CH3 . -4- (15) 8. Do one of the following 2 parts - cross out 1 of the parts. a) Starting with toluene, illustrate a preparation of l-phenyl-2-butanone. b) Illustrate the synthesis of ethyl cyclopentanecarboxylate with the use of malonic ester. -5- (6) 9. Draw a circle (just one) around the most acidic hydrogen (or hydrogens) in the following molecule. CH3 v _ C02CH2CH3 -6-