2007_Exam_1 - O O O A B C 4. a. (10 pts) Rank the three...

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1st Hour Exam Organic Chemistry c3046y Wednesday, Feb. 7, 2007 Prof. Leighton The exam is 5 pages long ( not including this one). Please make sure you have all of the pages. . . Question 1 (20 pts): Question 2 (20 pts): Question 3 (20 pts): Question 4 (20 pts): Name: ID#__________________________ Write your name on every page. . Question 5 (20 pts): Total (100 pts):____________ Signature:__________________________ Write complete but succinct answers. Good Luck!
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Name: Page 1 1. Provide detailed mechanisms to account for the following transformations. b. (10 pts) a. (10 pts) R N O Me Me 1. KOH, H 2 O, Δ 2. H 3 O + R OH O HO Me MeO OMe O OMe Me H +
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Page 2 Name: 2. Predict the major product of the following reactions: a. (10 pts) b. (10 pts) OH OH C N 1. , H + Me Me O 2. i. EtMgBr ii. H 3 O + , (quench) 3. H 3 O + 4. H + 1. i. LiMe 2 Cu ii. H 3 O + 2. H 2 N-NH 2 ; KOH, H 2 O, Δ O Me
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Name: Page 3 3. For each of the reactions below, show the product and provide a mechanism for its formation. a. (10 pts) b. (10 pts) O R O O O H O O 1. 2 equiv MeLi 2. H 3 O +
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Name: Page 4 b. (10 pts) Predict the product and provide a mechanism for its formation:
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Unformatted text preview: O O O A B C 4. a. (10 pts) Rank the three ketones shown below in order of increasing C=O stretching frequency in the IR spectra. lowest frequency highest frequency intermediate frequency CH 3 O PPh 3 CF 3 N H CH 3 Name: Page 5 Me O Me O MeO Me O OMe OMe MeO 5. a. (10 pts) By simple resonance arguments, the C=O IR stretches of the first two compounds shown below make sense. By the same reasoning, we would expect the compound on the right to have a C=O IR stretching frequency even lower than 1675 cm-1 . As you can see, this is not the case. Provide an explanation for the unexpectedly high C=O IR stretching frequency of the compound on the right. b. (10 pts) Sulfur ylids do several reactions that Phosphorous-based ylids do not. Here is one. Provide a mechanism for this unusual epoxidation reaction. ~1700 cm-1 ~1690 cm-1 ~1675 cm-1 O H 2 C S Ph Ph + O...
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2007_Exam_1 - O O O A B C 4. a. (10 pts) Rank the three...

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