CHEM 263 - Exam Ia - June 1, 2007

CHEM 263 - Exam Ia - June 1, 2007 - Chemistry Department...

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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. (2 x 9 + 1 – 7 + 2)/2 = 7 b. List the possible functional groups gleaned from the molecular formula. primary amine secondary amine tertiary amine nitrile amide alcohol aldehyde ether ketone phenol c. What functional group(s) is/are present? Omit the benzene ring. nitrile and ketone d. Propose a structure for this compound. 2. Sketch the expected 1 H NMR spectrum of the following compound:
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3. Give the structure(s) of the principle organic products of the following reactions: a. b.
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c. 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.
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Which is the product of thermodynamic control? 5.
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CHEM 263 - Exam Ia - June 1, 2007 - Chemistry Department...

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