2008Test3Review - page 5 of 7 (a) nucleophile electrophile...

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page 1 of 7 Name: _____________________________________ Class Number Midterm III Review , Spring 2008 Chemistry 2210 Professor S. A. Miller, April 8th, 2008
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page 2 of 7 Problem Number Possible Score Your Score 1 42 2 30 3 42 4 36 Total 150 Last Name: _________________ First Name: _______________ Signature: ___________________________________________
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1. (42 pts.; 7 pts. each) Draw the following. CHM 2210 Midterm III Review page 3 of 7 (a) A reaction energy diagram for the hydrogenation of isobutylene and indicate Δ H of the reaction and its value. (b) An anti-Bredt olefin. (c) A mercurinium ion.
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1. (continued) CHM 2210 Midterm III Review page 4 of 7 (d) An alkene for which hydroboration and H 2 SO 4 /H 2 O would give the same product. (e) A glycol. (f) Draw a hydrocarbon with 3 units of unsaturation and a p K a of 25.
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2. (30 pts.; 12 pts. mech.; 3 pts. per box) Provide detailed mechanisms, with arrows, for the following transformations. And, check the box that describes the function of the alkene or the mode of polymerization. CHM 2210 Midterm III Review
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Unformatted text preview: page 5 of 7 (a) nucleophile electrophile O H 3 O H 2 O OH OH (b) anionic cationic H 2 O/BF 3 + O H O O polymerization radical O H BF 3 3. (42 pts.; 7 pts. each box) Fill in the blanks with starting materials, intermediates, or products. CHM 2210 Midterm III Review page 6 of 7 (a) CH 2 I 2 Zn, CuCl (starting material) (b) Ph H 3 C (intermediate) (final product) (c) 1) Hg(OAc) 2 , MeOH 2) NaBH 4 (final product) (d) OsO 4 , H 2 O 2 (final product) (e) HgSO 4 , H 2 SO 4 , H 2 O (final product) BH 3 THF H 2 O 2 NaOH/H 2 O 4. (36 pts.; 4 pts. each box) In organic chemistry one often has to apply the principles of multstep synthesis to achive a desired target. Each of the following reactions can be accomplished in two transformations. Provide the conditions and the intermediate to complete the sequences. (A "transformation" could require two sequential steps, as in oxymercuration/demercuration.) CHM 2210 Midterm III Review page 7 of 7 (a) (b) (c) H H CH 3 HO Br OH O O Br Br...
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2008Test3Review - page 5 of 7 (a) nucleophile electrophile...

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