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225Sp04 Test 3 - CHEMISTRY 225 TEST#3 JUNE 4 2004 1(14 2(18...

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CHEMISTRY 225 TEST #3 1. ________ (14) JUNE 4, 2004 2. ________ (18) NAME _______________________________________________ 3. ________ (29) G O O D L U C K ! 4. ________ (14) TOTAL (75) Atomic numbers: H = 1, C = 6, N = 7, O = 8, S = 16, Cl = 17, Br = 35 1. (14 Points) CHIRAL AMINO ACIDS. (-)- Threonine (structure to the right and Test #2) is one of two naturally occurring amino acids (the other is isoleucine) with two stereogenic carbons. a. ( ________ / 6) (4) Determine the absolute configurations at the two stereogenic carbons of (-)-threonine. ( 2 ______ , 3 ______ ) (2) Would you expect the enantiomer of (-)-threonine to be dextrorotatory levorotatory optically inactive impossible to determine (circle one). b. ( ________ / 8) (4) Convert (-)-threonine to a Fischer projection with the longest carbon chain vertical. (2) Write a Fischer projection for the enantiomer of (-)-threonine. (2) Write a Fischer projection for a diastereomer of (-)-threonine. enantiomer diastereomer CO 2 H (-)-threonine NH 2 OH H CH 3 CO 2 H H (-)- threonine (CH 3 CHCHCO 2 H) OH NH 2
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