Final Exam - Chem 10172, Spring 2008 (1) FINAL EXAM KEY May...

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Chem 10172, Spring 2008 FINAL EXAM KEY May 7, 2008 1 (1) The biosynthesis of adrenaline includes the following reaction of S -adenosylmethionine (SAM) with ( R )- 1 : -O 2 C S NH 3 + CH 3 O HO OH N N N N NH 2 NH 2 HO HO HO H N HO HO HO H CH 3 Adrenaline S-adenosylmethionine (SAM) ( R )- 1 H H (a) (6 pts.) On the structure of SAM shown above, circle all the carbons that are chirality centers. See figure. (b) (6 pts.) On the structure of SAM shown above, draw a square around all the sp 2 - hybridized nitrogen atoms. See figure (remember resonance!) (c) (8 pts.) Using the structures drawn above , write a mechanism for this reaction using curved-arrow notation. (You may add lone pairs, or explicitly write out carbon or hydrogen atoms, if you wish, but please do not draw a fresh structure!) See figure. (d) (4 pts.) Suppose you examined a sample of the adrenaline product of this reaction in a polarimeter using plane-polarized light from a sodium D lamp. How would you expect the plane of polarization of the light to rotate as it passed through the sample? (Circle the best answer.) To the left To the right Can't tell which direction It would not from the available information rotate at all
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Chem 10172, Spring 2008 FINAL EXAM KEY May 7, 2008 2 (2) Consider the 3-bromo-2-methylpentane shown below, which has been stereospecifically labeled with deuterium at carbon-4 (D = 2 H). (The carbons in the main chain have been numbered for your convenience.) Br H D 1 2 3 4 5 (a) (5 pts.) Circle the configuration of C-3 (the carbon attached to the Br atom). R
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Final Exam - Chem 10172, Spring 2008 (1) FINAL EXAM KEY May...

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