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CHEM 263 - Exam Ia - June 3, 2005

CHEM 263 - Exam Ia - June 3, 2005 - Ether d Propose a...

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Chemistry Department University of Alberta CHEM 263 Exam I Friday, June 3, 2005 1. Give the product(s) of the following reaction at high temperature. If a mixture is expected, identify the major product. 2. Cyclopentadienone is a relatively unstable molecule and reacts rapidly at room temperature to form a compound of molecular formula C 10 H 8 O 2 . Remember this must be a reaction similar to those we have so far studied in 263! a. What “named” reaction is this? Diels – Alder reaction b. Suggest a structure for this molecule.
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3. The IR and 1 H NMR spectra of a compound of molecular formula C 10 H 12 O 2 are given below. Propose a structure for this compound. SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ (1-06-05) a. Calculate the degree of unsaturation. (2 x 10 – 12 + 2)/2 = 5 b. List the possible functional groups gleaned from the molecular formula. Alcohol Aldehyde Ketone Ether
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Carboxylic acid Ester c. What functional group(s) is/are present? Omit the benzene ring. Ketone
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Unformatted text preview: Ether d. Propose a structure for this compound. 4. Sketch the expected 1 H NMR spectrum of the following compound: 5. Draw the structure of 3-nitrobenzenesulfonic acid. 6. Name the following compound: 2,6-dibromo-4-chloroaniline 7. Could the following compound show aromatic character? Justify your answer. It is aromatic. It is cyclic, planar, with 6 p electrons delocalized over the ring. (2 electrons come from the sulfur, the other two would be associated with an sp 2 orbital of the sulfur) 8. Propose a mechanism to account for the following reaction: 9. Provide a synthetic pathway for the following transformation: 1. CH 3 Cl/AlCl 3 2. KMnO 4 or K 2 Cr 2 O 7 3. HNO 3 /H 2 SO 4 CHEM X6X Home Page | Faculté Saint-Jean | University of Alberta | Chemistry Department This page is maintained by Dr. Ed Blackburn ( [email protected] ), course instructor. Updated June 4, 2005...
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