Exam 3 - S2002

Exam 3 - S2002 - April 24th 2002 Page 1 of 18 April 24th...

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April 24th 2002 Dr. S. A. Dandekar CHEM 2380 Exam 3 (100 points) Name _________________________ Select the best answer for ANY 28 of questions 1-32 on the scantron sheet. You may answer more than the required number of questions if you wish. 1. In which of the following sequences are the compounds listed in order of decreasing acidity? a. CH 3 COOH > H 2 O > CH 3 CH 2 OH > HC CH > NH 3 b. CH 3 CH 2 OH > CH 3 COOH > H 2 O > HC CH > NH 3 c. CH 3 COOH > CH 3 CH 2 OH > H 2 O > NH 3 > HC CH d. H 2 O > CH 3 COOH > CH 3 CH 2 OH > HC CH > NH 3 e. CH 3 CH 2 OH > H 2 O > CH 3 COOH > HC CH > NH 3 2. Which reagent would best serve as a basis for a simple chemical test to distinguish between CH 3 CH 2 COOH and CH 3 COOCH 3 ? a. Concd H 2 SO 4 b. Br 2 /CCl 4 c. CrO 3 /H 2 SO 4 d. NaHCO 3 /H 2 O e. KMnO 4 /H 2 O 3. The product of the following reaction would be: O H + CH 3 CH 2 COH + CH 3 1 8 OH ——————> a. O CH 3 CH 2 C 1 8 OCH 3 b. 1 8 O CH 3 CH 2 COCH 3 c. 1 8 O CH 3 CH 2 C 1 8 OCH 3 d. O CH 3 CH 2 COCH 3 e. O Page 1 of 18 April 24th 2002 8/31/2007 http://www.chem.unt.edu/CHEM2380/2380EX3.htm
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CH 3 CH 2 OC 1 8 OCH 3 Page 2 of 18 April 24th 2002 8/31/2007 http://www.chem.unt.edu/CHEM2380/2380EX3.htm
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Exam 3 (100 points)--Page 2 4. The product, F, of the following sequence of reactions, CH 3 | LiAlH 4 H 2 O PBr 3 Mg CO 2 H + CH 3 CHCOOH ——————> A ———> B ————> C —————> D ———> E ———> F, Ether H 2 O would be: a. CH 3 | CH 3 CHCH 2 Br b. CH 3 | CH 3 CCH 2 COOH | Br c. CH 3 CH 2 CH 2 COOH d. CH 3 | CH 3 CHCH 2 COOH e. CH 3 | CH 3 CHCOOCH 3 5. The product, Z, of the following sequence of reactions is which compound? KMnO 4 H + SOCl 2 CH 3 CH 2 OH p -chlorotoluene —————————> W ———> X —————> Y ————————> Z OH - , heat base a. I b. II c. III Page 3 of 18 April 24th 2002 8/31/2007 http://www.chem.unt.edu/CHEM2380/2380EX3.htm
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d. IV e. V Page 4 of 18 April 24th 2002 8/31/2007 http://www.chem.unt.edu/CHEM2380/2380EX3.htm
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Exam 3 (100 points)--Page 3 6. A compound has the molecular formula, C 6 H 1 2 O 2 . Its IR spectrum shows a strong absorption band near 1740 cm - 1 ; its 1 H NMR spectrum consists of two singlets, at δ 1.4 and δ 2.0. The most likely structure for this compound is: a. O CH 3 CHOCCH 2 CH 3 | CH 3 b. O CH 3 CH 2 CH 2 OCCH 2 CH 3 c. O CH 3 | CH 3 CH 2 OC——CHCH 3 d. CH 3 O | CH 3 C——O——CCH 3 | CH 3 e. CH 3 O | CH 3 CH 2 C——OCH | CH 3 7. Which of the following reactions would constitute a reasonable
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Exam 3 - S2002 - April 24th 2002 Page 1 of 18 April 24th...

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