Practiceexam2 - 1 Heating a mixture of 1,3-diphenylacetone and acrolein in trimethylamine gives a product C18H16O in 53 yield The mechanism for

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1. Heating a mixture of 1,3-diphenylacetone and acrolein in trimethylamine gives a product, C 18 H 16 O, in 53% yield. The mechanism for product formation is believed to be a Michael addition followed by an intramolecular aldol condensation. Which of the following is the product of this reaction? C 6 H 5 CH 2 CCH 2 C 6 H 5 + H 2 C=CHCH OO N(Et) 3 heat O Ph Ph O Ph Ph CHO Ph Ph O Ph Ph CH 3 1) 2) 3) 4) A) is 1 B) is 2 C) is 3 D) is 4 2. Which carbon atoms are most susceptible to nucleophilic attack? 3 CH=CHCCH 3 O A B C D A) A and B B) B and C C) B and D D) A and D Page 1
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3. What is the product of the following intramolecular aldol condensation reaction? H O H O KOH, CH 3 OH heat O O CHO CHO 1) 2) 3) 4) A) is 1 B) is 2 C) is 3 D) is 4 4. Benzalacetone is the crossed aldol condensation product formed between benzaldehyde and acetone. Which of the following is the structure of benzalacetone? 1) C 6 H 5 CH=CHCCH 3 2) C 6 H 5 CH=C(CH 3 ) 2 2) C 6 H 5 CCH=CHCH 3 4) C 6 H 5 CH 2 CCH=CH 2 O OO A) is 1 B) is 2 C) is 3 D) is 4 5. Which one of the following reagents adds a methyl group by conjugate (1,4-addition) addition to an α , β -unsaturated ketone or aldehyde? A) LiCu(CH 3 ) 2 B) CH 3 MgBr C) Hg(O 2 CCH 3 ) 2 D) CH 3 Li Page 2
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6. Which one of the following gives ethanal, CH 3 CH=O, (as one of two products) when added to an aqueous solution of HCl? A) is 1 B) is 2 C) is 3 D) is 4 7. Acid-catalyzed hydrolysis of the cyclic acetal below gives: O O Cl A) ethanal and 2-chlorocyclohexanol B) 1,2-ethanediol and 2-chlorocyclohexanol C) ethanol and 2-chlorocyclohexanol D) 1,2-ethanediol and 2-chlorocyclohexanone 8. What is the final product of the following sequence of reactions? (CH 3 ) 2 CHOH PBr 3 Mg 1) PCC diethyl ether 2) H 3 O + CH 2 Cl 2 O 1) (CH 3 ) 2 CHOCH 2 CH 2 OH 3) (CH 3 ) 2 CHCH 2 CHO 2) (CH 3 ) 2 CHCCH 3 4) (CH 3 ) 2 CHCH 2 CO 2 H O A) is 1 B) is 2 C) is 3 D) is 4 Page 3
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9. Consider the three compounds below.
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This note was uploaded on 02/19/2009 for the course CHM 241B taught by Professor Dr.koerner during the Fall '08 term at University of Arizona- Tucson.

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Practiceexam2 - 1 Heating a mixture of 1,3-diphenylacetone and acrolein in trimethylamine gives a product C18H16O in 53 yield The mechanism for

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