Exam3.1992

Exam3.1992 - Exam 3 Chemistry 212 Dr M W Thomson 1)—20...

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Unformatted text preview: April 24, 1992 _ Exam 3 - Chemistry 212 Dr. M. W. Thomson 1)—20 points- Circle the best answer for each question. a) The most acidic compound. CH3CH20H cmcozcmcu3 CH3COCH2CO~2CH3_ CH3C0CH2COCH‘3. b) The least basic compound. . - NHZ NH 2 NH 2 NH 2 t i ‘No Q - . 2H3 N02 2 CH3 c) The compound that cannot be used in the preparation of a polyester. HOCHZCHZOH CH3CH2C02H HOZCCHZCHZCHZCOZH HOCHZCH(OH)CH20H d) The aldehyde that has no OL-hydrogen atoms. ethanal benzaldehyde . acetone 2-methylpropanal benzophenone e) The repeat unit of a polyamide. -(NH2CH2CH2CH2CO)- -(CH2CH2CH2CH2NH2)- -(CH2CH2CH2NH2)- -(CH2CH2COCH2CH2NH2)- 2)-20 points-Provide a detailed, step-by—step mechanism for the condensation reaction below. Clearly draw afl intermediates in the mechanism. 1)Na+CH3CH20', ethanol 2) cold dilute HCl ethyl ethanoate --------------------------- --> ethyl acetoacetate 3)—40 points-Complete the following reactions by providing the structural formula for the major product of each reaction. Show any stereochemistry. If no reaction will occur, then write N.R. for the answer. 1) LDA, THF, 0°C 2) phenyl selenium bromide 3) H202 a) 2-methylcyclopentanone -------------------------------------- -—> D20, Na2C03 b) Cyclopentanone _ ........................... _-> 1) LiAlH4, ether 2) H20 c) propanamidc .......................... -_> 1) Na+CH3CH20', ethanol 2) benzyl bromide 3) dilute HCI, 85°C (1) diethyl rnalonate -------------- -4 ------------- --> dilute HCl, room temperature e) triethylamine ------------------------------- --> NaOH, ethanol, 55°C 0 2,5—hexan'edione ----------------------- --> 1) excess iodomethane, ether 2) silver oxide, water 3) 140°C g) 2-aminopentane ---------------------------- --> NaNOz, HCl (aq), 0 °C h) dipropyl amine ............................ __> . benzoyl peroxide, 50 °C i) styrene ---------------------------- ——> 4)-20 points-Provide a mechanistic explanation for the following reactions. 0 OH 0 .o M an I an —————-——-—> b) _ 0 1) NaN3 NHZ Cl 2) 100 °C ' 3) H20 —-———-> ...
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Exam3.1992 - Exam 3 Chemistry 212 Dr M W Thomson 1)—20...

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