CHEM 263 - Exam Ia - June 2, 2006

CHEM 263 - Exam Ia - June 2, 2006 - Chemistry Department...

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Chemistry Department University of Alberta CHEM 263 Exam I Friday, June 2, 2006 1. The IR and 1 H NMR spectra of a compound of molecular formula C 10 H 12 O are given below. Propose a structure for this compound. SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ (31-05-06)
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a. Calculate the degree of unsaturation. degree of unsaturation = (2 x 10 – 12 + 2)/2 = 5 b. List the possible functional groups gleaned from the molecular formula. alcohol, aldehyde, ketone, or ether c. What functional group(s) is/are present? Omit the benzene ring. aldehyde d. Propose a structure for this compound. d (ppm) multiplicity # Hs assignment 9.96 s 1 aldehyde proton 7.80 d 2 Hs ortho to aldehyde 7.38 d 2 Hs ortho to isopropyl 2.97 heptet 1 tert H of isopropyl 1.28 d 6 methyl Hs of isopropyl 2. Sketch the expected 1 H NMR spectrum of the following compound:
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3. Predict the products of the reaction of hydrogen chloride with 2-methyl-1,3- butadiene under the following conditions and propose a mechanism for their formation: a. Kinetic control b. Thermodynamic control
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4.
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CHEM 263 - Exam Ia - June 2, 2006 - Chemistry Department...

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