CHEM 3580- Exam II Summer 2012.pdf

CHEM 3580- Exam II Summer 2012.pdf - Cornell University...

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Cornell University Chemistry 3580 Exam II July 27, 2012 Instructions: Read all questions completely before answering. You may find it helpful to first answer those questions that you find easier and then return to those you find more difficult. Please follow the directions for each question as answers that are not written where or how it is specified in the question will lose all credit. Good Luck!!! Problem Score Possible 1 18 2 13 3 13 4 20 5 13 6 13 7 13 8 13 9 13 10 11 11 11 12 11 13 11 14 13 15 14 16 6* Total 200 *denotes bonus points Name:___________________________________________________ Signature:________________________________________________
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Page 1 of 11 1) ( 18 ) Provide IUPAC names for each of the following compounds or, when a name is given, draw the corresponding structure. In order to receive any credit, your answer must be written on the line next to each problem. Be sure to include any stereochemical designations, where appropriate. A) O O B) O C) O O D) HO O E) O N H F) O Cl
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Page 2 of 11 2) ( 13 ) Propose a reasonable mechanism to account for the formation of the following observed reaction product(s). Br O NLi O O
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Page 3 of 11 3) ( 13 ) Propose a reasonable mechanism to account for the formation of the following observed reaction product(s). O O H 3 O + O OH HO
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Page 4 of 11 4) ( 20 ) In the left hand column, there is a product drawn of an Aldol condensation between two starting materials. One of the starting materials forms an enolate anion ( donor ) and attacks the carbonyl ( acceptor ) molecule that, upon quenching, results in the product shown. At the bottom of the page are possible choices for the donor and acceptor molecules. Using the letters of each molecule, identify the donor and acceptor molecule that, when reacted in base (and then quenched), would result in the desired product. Please not some compounds may be used more than once (as donor or acceptors for the products shown), while others may not be used at all. Write the letter for each donor and acceptor on the line in the proper column next to each product. : Product Donor (Enolate) Acceptor (Carbonyl) O H OH A) B) O OH C) O H D) OH O E) O O O O Compound Choices: O H O O H H H O O O O O O H H O H O A B C D E F G H
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Page 5 of 11 5) ( 13
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