practice_final - Massachusetts Institute of Technology...

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Massachusetts Institute of Technology 5.13: Organic Chemistry II December 19,2005 Final Exam Question 1 11 0 points Question 2 - I1 5 points Question 3 - I30 points Question 4 points Question 5 11 0 points Question 6 - 5 points Question 7 0 points Question 8 - 11 2 points Question 9 I1 0 points Question 10 I1 2 points Question 11 - I1 2 points Question 12 - points Question 13 - I1 2 points 01 Question 4 - I1 4 points Question 15 6 points 1200 points Name (printed) Name (signed) T. A. There are 18 pages (2- 19) of questions in this exam. Page 1 of 19
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2 1. (10 points total) Write an arrow-pushing mechanism for the reaction below. + + H H O * heat H H N Me O * Note: Aste risk(*)= 13 C. OH Me N H O OH Figure by MIT OCW.
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3 2. ( 15 points total ) Compound A is prepared from B and C and has the spectroscopic data listed below. Draw the structure of A in the box provided, and write an arrow-pushing mechanism for its formation from B and C in the space below. O OH Ph CH 3 O C A B N N Catalytic H + Heat 7.05-7.15, m, 5H 5.80, t, J = 6.3, 1H 3.67, t, J = 6.5, 4H 3.47. t , J = 6.5, 4H 3.22, d, J = 6.3, 2H 2.34, t, J = 7.4, 2H 2.12, t, J = 7.4, 2H 1.71, s, 3H 1685 cm -1 Molecular weight 273.17 Data for A: 1 H NMR (ppm) IR + Figure by MIT OCW.
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4 3. (30 points total, 1 point per box) For the following 15 structures, write the number of chemically non-equivalent (number of “different types”) of hydrogens and carbons in the appropriate boxes below. (Be careful to put the numbers in the correct boxes – we can’t read your mind, i.e. wrong numbers will receive no credit – no exceptions.) CH 3 CH 3
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This note was uploaded on 11/27/2011 for the course CHEMICAL E 20.410j taught by Professor Rogerd.kamm during the Spring '03 term at MIT.

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practice_final - Massachusetts Institute of Technology...

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