Fall07FinalExamKey - I(40 points Name Page 1 F.07.210FEP1(a...

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Name _______________________ Page 1 F.07.210FEP1 I. (40 points) (a) Provide the curved-arrow mechanism for the following transformation. CH 3 S CH 3 + Br Br S CH 3 CH 3 Br Br Compound A (b) What is the best mechanistic label that describes the reaction that forms Compound A ? (c) Using the VSEPR model, what would be the expected hybridization for the sulfur atom in Compound A ? (d) What would be the observable geometry at the sulfur atom of Compound A ? (e) The pK a values for the hydrogen atoms in Compound B are provided here. Draw the set of three resonance structures (all atoms closed shell, formal charges restricted to -1,0,+1) for the conjugate base derived from deprotonation of the most acidic site. Include the non-bonding electrons in your drawings. O O CH 3 CH 3 H H H H H H 6 20 47 20 Compound B (f) If the IUPAC name for acetone [(CH 3 ) 2 C=O] is 2-propanone (or, propan-2-one), then what is the IUPAC name for Compound B ? (g) Compound A is observed to be a source of electrophilic bromine. Based on the information on this page, what is the product from the following reaction? O O CH 3 CH 3 H H H H H H S CH 3 CH 3 Br Br 2) 1) LiH + LiBr + (CH 3 ) 2 S + H 2 5 5 3 5 9 8 5 circle one: S N 1 A E Bronsted acid/base S N 2 E1 EAS E2 A N E1cb pK a = pK a = pK a = pK a = sp 3 pyramidal or trigonal pyramidal O O CH 3 CH 3 H H H H H O O CH 3 CH 3 H H H H H O O CH 3 CH 3 H H H H H 5,5-dimethyl-1,3-cyclohexanedione 5,5-dimethylcyclohexane-1,3-dione OR O O CH 3 CH 3 Br H H H H H no partial no partial no partial no partial no partial nbe NOT needed; however, wrong nbe is -2 -3 per class of error - numbering, prefix, punct, suffix, main chain 3 per correct structure (showing the H's is optional)
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Name _______________________ Page 2 F.07.210FEP2 II. (40 points) A. When Compound C is heated in methanol (CH 3 OH), there are two isomeric products formed (Compounds D and E ). Provide a complete, step-wise mechanism for the formation of Compound E from Compound C . You may use H-B for a general Bronsted acid, and B for its conjugate base, as needed.
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This note was uploaded on 02/18/2011 for the course CHEMISTRY 210 taught by Professor Nolta during the Winter '10 term at University of Michigan.

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Fall07FinalExamKey - I(40 points Name Page 1 F.07.210FEP1(a...

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