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Past Exam for CHEM 241 - Organic Chemistry II with Davis at Maryland (UMD)

Exam Information

Material Type:Exam 2
Professor:Davis
Class:CHEM 241 - Organic Chemistry II
Subject:Chemistry
University:University of Maryland
Term:Fall 1994
Keywords:
  • Testosterone
  • Macromolecules
  • Unsaturated
  • Chemical Shift
  • Continuation
  • Substitution
  • Conformation
  • Nmr Spectrum
  • Intermediate
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Sample Document Text

. "CHEM 243 Davis Exam #2 Oct. 27, 1994 Name TA Section There are 4 questions and 7 pages. Check your exam before proceeding. 1. (30 pts) 2. (65 pts) 3. (35 pts) 4. (20 pts) Total (150) Davis Exam 2 Page 1 1. Show the sequence of steps required to convert compound 1 to compound 2. Indicate the reagents needed to perform each step and indicate all intermediates. (30 pts) ... 1 2 Davis 243 Exam 2 Page 2 2. (75 pts) Testosterone 1 is prepared from diketone 2. o 2 Testosterone 1 a) Show the stepwise mechanism for base-catalyzed formation of 1 from 2. Provide all intermediates. (15 pts) Davis 243 Exam 2 b) Draw the enol tautomer of testosterone 1. (5 pts) c) Indicate the product of the following transformations on testosterone 1 (20 pts). o Testosterone 1 1 1 1 Acetyl Chloride NEt3 1) LiAIH4 2) Acetyl Chloride, NEt3 1) HOCH 2 CH 2 0H, H+ 2) OS04 3) NaI0 4 Page 3 Davis Chern 243 Page 4 d) The female hormone estradiol 4 exists...

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