Chem239A, Final Exam#2

Chem239A, Final Exam#2 - A , B and coniine. N...

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CHEM 239A Summer, 20089 FINAL EXAM #2 Name . Prof. Sasaki 85 points TOTAL Good Luck! Note: Only answers in the box will be graded. ______________________________________________________________________ 1. (28) (a) Draw a stepwise mechanism for the following reaction. N C N tBoc-Gly CH 2 -NH 2 CH 3 H 3 C CH 3 O N H O O H N + N H N H O (b) Draw the structure of the following compounds. (i) isopentenyl pyrophosphate (ii) adenosine triphosphate (iii) a tertiary amide
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CHEM 239A page 2 Name . 2. (27) (a) Carefully circle the isoprene units in the following terpines, and label each as a monoterpine, sesquiterpine, or diterpine. (i) (ii) O O (iii) O O CH 3 CH 3 O CH 3 (b) Coniine, C 8 H 17 N, is the toxic principle of poison hemlock drunk by Socrates. Coniine has only one tetrahedral stereocenter (S-isomer). The following reactions were carried out starting from coniine. Write the structures of compounds
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Unformatted text preview: A , B and coniine. N 5-(N,N-dimethylamino)-1-octene (C 10 H 21 N) 1) Ag 2 O 2) heat compound B (C 10 H 22 NI) excess CH 3 I compound A (C 10 H 19 NO) acetic anhydride pyridine Coniine (C 8 H 17 N) A B Coniine CHEM 239A page 3 Name . 3. (30) (a) Sodium nitrite, a food preservative used in meats, causes the mutation of cytosine into uracil under acidic conditions. Propose a mechanism. N N O NH 2 NaNO 2 H + H 2 O N NH O O (b) Predict the major product(s) for each of the following reactions. If more than one product is expected, please put all of them in the box. (i) CF 3 Br 1) Mg, diethyl ether 2) CO 2 3) H 3 O + (ii) CH 2 COOCH 2 CH 3 CH 2 COOCH 2 CH 3 H H 1) NaOCH 2 CH 3 2) H 3 O + (iii) C 6 H 12 O 3 Product of (ii) 1) OH-, H 2 O 2) H 3 O + 3) heat C 6 H 8 O...
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This note was uploaded on 01/19/2012 for the course CHEM 239 taught by Professor Sasaki during the Summer '06 term at University of Washington.

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Chem239A, Final Exam#2 - A , B and coniine. N...

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