Spring 09 Exam 4 - CHEMISTRY 225 TEST#4 JUNE 12,2009 NAME...

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CHEMISTRY 225 TEST #4 JUNE 12,2009 NAME 3. (28) Useful atomic numbers: H : l, C = 6,N : 7, O : 8, Si : 14, Cl= 17, Br = 35 4._ (10) TOTAL (75) GOOD LUCK, AND USE MODELS! l. (22 Points) STRUCTURES AND FORMULAS. a.(-/6)Providestrucfuressatisffingeachofthefollowingdescriptions. meso'1,3dibromo- cyclohexane Bicyclo[2.2. 1 ]heptane frans- 1 +h loro-3-methyl- cyclopentane b. ( _ / 4) From the menu of cyclic compounds below, select the structures that satisfy the descriptions. Each bullet is worth one point. OH OH OH /.------/T. ...-OH L----Jct ABCD r a pair of enantiomers - and - r a pair of diastereomers - and o Two representations of the same stereoisomer - and o To which of the molecules above does the chair cyclohexane on the right correspond?
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c. ( _ / 7) Consider bicyclo[3.2.1]octane, the bridged bicyclic hydrocarbon below. bicyclo[3.2.1]octane spirocyclic isomer o (l) What term describes the conformation of the six-membered ring of bicyclo[3.2.l]octane? o (4) Directly on the structural formula -Draw in a set of eclipsed hydrogens. Label them as H. . -Write in all bridgehead hydrogens. Label them as H6. -Highlight the three-carbon bridge o (2) Write a structure for a spirocyclic structural isomer of bicyclo[3.2.l]octane d. ( _ / 5) l-Threonine is one of two common amino acids with tlo stereogenic carbons. A structural formula for t-threonine is shown to the right. !-_ Shown below is a Fischer projection for o-threose, a simple sugar. o-Threose and t-threonine, have the same relative configurations at both of their stereogenic carbons. Write Fischer projections for t--threonine and its enantiomer, D-threonine. NOTE: the carboxyl group should be at the top. NHa
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Spring 09 Exam 4 - CHEMISTRY 225 TEST#4 JUNE 12,2009 NAME...

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