CHEM 263 - Exam I - June 1, 2007

CHEM 263 - Exam I - June 1, 2007 - the nitrogen in the...

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Chemistry Department University of Alberta CHEM 263 Exam I Friday, June 1, 2007 1. The IR and 1 H NMR spectra of a compound of molecular formula C 9 H 7 NO are given below. SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ (30-05-07)
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a. Calculate the degree of unsaturation. b. List the possible functional groups gleaned from the molecular formula. c. What functional group(s) is/are present? Omit the benzene ring. d. Propose a structure for this compound. 2. Sketch the expected 1 H NMR spectrum of the following compound: 3. Give the structure(s) of the principle organic products of the following reactions: a. b. c.
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4. When a solution of 1,3-butadiene in CH 3 OH is treated with chlorine, the products are the following: a. Propose a mechanism to account for their formation. b. Which is the product of thermodynamic control? 5. Imidazole is an aromatic compound: a. Justify the aromatic character of imidazole. b. Reactions of imidazole with simple electrophiles such as a Bronsted acid occur selectively at
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Unformatted text preview: the nitrogen in the 3-position and not at the 1-nitrogen position. Briefly explain why this should be true. c. Is the following molecule aromatic? Explain your answer. 6. Name the following compound: 7. Draw the structure of 2-chlorobenzenesulfonic acid. 8. The nitration of N , N-dimethylaniline, C 6 H 5 N(CH 3 ) 2 , in 85% H 2 SO 4 gives 45% m-nitro product and 38% p-nitro product. (The remainder is polynitrated product and no typing error has been made!) a. What is the species actually undergoing nitration to give the meta product? b. How is it formed? c. What is its relative reactivity to that of benzene? (Give an explanation of your answer.) CHEM X6X Home Page | Facult√© Saint-Jean | University of Alberta | Chemistry Department This page is maintained by Dr. Ed Blackburn ( [email protected] ), course instructor. Updated June 1, 2007...
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This note was uploaded on 07/05/2008 for the course CHEM 263 taught by Professor Blackburn during the Summer '06 term at University of Alberta.

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CHEM 263 - Exam I - June 1, 2007 - the nitrogen in the...

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