http___rutchem.rutgers.edu_Co...ctice_Exam_I_Chem_315_F08

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(b) Draw the meso stereoisomer of 2,3-difluorobutane, using the wedge-dash representation of stereochemistry AND a Fischer projection. (c) Draw a diastereomer of each of the compounds shown below.
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2. (a) Draw the indicated number of most important additional resonance forms of the structures shown below, and then number all of the resonance forms in order of their importance as contributers to the overall structure (1 = most important, etc.). (b) Draw a p-orbital diagram representing the highest occupied molecular orbital (HOMO) of 1,3-butadiene. (c) Explain why all the atoms in 1,3-butadiene are coplanar in the lowest energy conformer of this molecule.
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Unformatted text preview: 3. (a) (R)-2-bromobutane has a specific rotation of – 23.1 deg.mL.g-1 .dm-1 . The optical rotation observed for a 2.0 g/mL solution of 2-bromobutane was measured in a cell with pathlength of 10 cm as +23.1 degrees. (i) What percentage of the 2-bromobutane is the (R) enantiomer? (ii) What is the enantiomeric excess of the (S) enantiomer? (b) In each of the structures shown below, indicate whether the hydrogens labeled Ha and Hb are enantiotopic or diastereotopic, and which is the pro-R hydrogen and which is the pro-S hydrogen. (c) Write a synthetic scheme that would convert 2-butyne into a meso compound....
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