Prelim 2-S10 - Answers

Prelim 2-S10 - Answers - Name(Last(First(Middle Initial...

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Name: (Last) (First) (Middle Initial) 1 Circle Lecture time – 9:05 or 10:10 Organic Chemistry for the Life Sciences Chemistry 3580 Spring Semester 2010 Prelim 2 March 16, 2010 7:30-9:00 PM Read each question very carefully. There are 11 total pages. Please, count your pages before Beginning the exam. Write all answers only on the printed side of the exam. Draw structures clearly. You may do rough work on the back of each page. But note that nothing on backside will be graded . 1. (8) 2. (16) 3. (24) 4. (12) 5. (22) 6. (12) 7. (6) Total (100)
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Name: (Last) (First) (Middle Initial) 2 1. ( 8 Points) (a) Compounds (A-C) undergo typical nucleophilic substitution reaction as shown below. OH O L L O HO OH O L 1 2 Select the compound that would give the highest rate and one that would give the lowest rate in each step. O O O O NO 2 B C O O A Step 1: (Steric effect – accessibility; B has the least steric hindrance. C is the most sterically hindered. For C, steric and electronic effects (electron-withdrawing effect of NO 2 ) oppose each other) Highest rate B Lowest rate C Step 2: (Leaving group ability – resonance stabilization of nitrophenoxide => weak base => good leaving group; benzyl alkoxide is a stronger base => poor leaving group) Highest rate C Lowest rate B (b) Circle the compound that will exhibit the highest reactivity with HO . Succinic anhydride ! -Butyrolactam ! -Butyrolactone (c) From the list below select the compound that you would expect to have (i) the lowest pKa and (ii) the highest pKa. O O O O A B C Effect of resonance delocalization (i) Lowest pKa B (ii) Highest pKa A
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Name: (Last) (First) (Middle Initial) 3 2. (16 Points) Provide the reagents that you would use to carry out the following transformations. Write down your answers in the spaces provided in table below. Related to many questions in Problem Sets 5A, 5B and 6
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This note was uploaded on 10/24/2010 for the course CHEM 3580 taught by Professor Sogah, d during the Spring '08 term at Cornell.

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Prelim 2-S10 - Answers - Name(Last(First(Middle Initial...

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