Sasakiexam1 - CHEM 239U Spring, 2005 Prof. Sasaki EXAM #1...

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CHEM 239U Spring, 2005 EXAM #1 Name . Prof. Sasaki 150 points TOTAL Good Luck! Note: Only answers in the box will be graded. ________________________________________________________________________ 1. (35) (a) Acetic acid has a boiling point of 118 °C, whereas its methyl ester has a boiling point of 57 °C. Briefly explain why the boiling point of acetic acid is higher than that of its methyl ester, even though acetic acid has a lower molecular weight. (b) In each set, assign the acid its appropriate pKa. (i) OH O and OH O (pKa 4.8 and 4.3) (ii) COOH O and COOH O (pKa 3.58 and 2.49) (iii)
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CH 2 COOH C H 3 C H 3 C H 3 C and CCH 2 COOH N (pKa 5.3 and 2.45)
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CHEM 239U page 2 Name . 2. (35) (a) Treating choline with acetic anhydride in the presence of pyridine gives acetylcholine, a neurotransmitter. Draw a reasonable mechanism for the reaction. (CH 3 ) 3 NCH 2 CH 2 OH N Choline Pyridine (b) N,N-Diethyl-m-toluamide (DEET) is the active ingredient in several common insect repellents. Show how you would synthesize DEET from 3-bromotoluene and any other
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Sasakiexam1 - CHEM 239U Spring, 2005 Prof. Sasaki EXAM #1...

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