Exam2.1992

Exam2.1992 - 0 March 27, 1992 Exam 2 - Chemistry 212 Dr. M....

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Unformatted text preview: 0 March 27, 1992 Exam 2 - Chemistry 212 Dr. M. W. Thomsen 1)-20 points-Circle the best answer for each question. a) The alkyl halide least desirable to use in a Williamson ether synthesis: CHSI CH3CH2Br CH3CH2C1 (CH3)2CHC1 (CH3)3CC1 b) The most acidic compound: CH3C02H FCHZCOZH ClCHZCOZH CH3CHZOH (£300ch3 c) The compound most susceptible to reduction by NaBH4: CH3C02CH3 CH3C02CH(CH3)2 CH3COCH3 CH3CHO CH3OCH3 d) The compound that is n_o_t a carboxylic acid derivative: CH3C02CH3 CH3CONH2 CH3CH2CN CH3CO-O-COCH3 CH3CH(OCH3)2 e) The compound that exhibits a C=O infrared absorption furthest from 1800 cm'l: CH3CH2CHO CH3CH2C02CH2CH3 o A o o NH2 CH3 (:1 2)-40 points—Complete the following reactions by providing the structural formula for the major product(s) of each reaction. If no reaction will occur, then write N .R. for the answer. a) b) d) g) h) j) 3—pentanone acetyl chloride cyclopentanone l-butanol cyclohexanecarboxylic acid benzaldehyde ethyl methanoate acetic anhydride triphenyl phosphine bromobenzene dimethyl amine, solid N aOH _______________________________ __> NH2NH2, H20, KOH, 100°C ________________________________ __> 1) NaH, ether 2) CH3CHZI, ether 1,2-ethanediol, HCl __________________________ __> 1) phenyl magnesium chloride (2 equivalents) 2) dilute HCl ____________________________________________ __> 1) 2-bromopropane, THF 2) butyl lithium, THF 3) 2-propanone _____________________________ __> 1) Mg, anhydrous ether 2) carbon dioxide 3) dilute HCI ---. -------------------- —-> 3)-20 points-Consider the reaction below and then work the problem. COZH H+ O + CH3CH20H a) Provide a detailed, step—by-step mechanism for the reaction. b) Briefly describe the means by which the yield of ethyl benzoate may be maximized. COZCHZCH3 + H20 4)-20 points-Consider the reaction below and then work the problem. 0 NOH NH20H, pH 4.5, 25°C I -—> a) Provide a detailed, step-by-step mechanism for the reaction below. Clearly draw all intermediates in the mechanism. b) When the reaction is performed at pH 2.2, the rate of the reaction decreases substantially. Explain this decrease in reaction rate. ...
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Exam2.1992 - 0 March 27, 1992 Exam 2 - Chemistry 212 Dr. M....

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