F.08.215.E2K - Chemistry 215 Second Examination October 29,...

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Chemistry 215 Name ___________________________________ Second Examination please print clearly please print clearly October 29, 2008 Signature ________________________________ (1.5 hr; 120 points) ID No. _______________________ Please CHECK OFF your Chemistry 216 laboratory section: 130 T 1-5 PM A636 Dustin Patterson 131 T 1-5 PM A618 Peter Ung 132 T 1-5 PM A606 Li Wang 133 T 1-5 PM A642 Yuta Suzuki 134 T 1-5 PM A624 Jing Chen 135 T 1-5 PM A630 Jiumei Chen 136 T 1-5 PM A612 Travis Clark 150 W 12-4 PM A606 Dustin Patterson 151 W 12-4 PM A612 Peter Ung 152 W 12-4 PM A618 Tasha Francis 153 W 12-4 PM A624 Amanda Ward 154 W 1-5 PM A630 Jiumei Chen 155 W 1-5 PM A636 Tom Sundberg 176 W 1-5 PM A642 Jonathon Mahlow 170 TH 1-5 PM A606 Li Wang 171 TH 1-5 PM A612 Travis Clark 172 TH 1-5 PM A618 Tasha Francis 173 TH 1-5 PM A642 Yuta Suzuki 174 TH 1-5 PM A636 Tom Sundberg 175 TH 1-5 PM A624 Jing Chen 156 TH 1-5 PM A630 Amanda Ward PUT AN “X” HERE IF YOU ARE NOT IN CHEM 216: _________ Prob Pts Score GSI I 30 \___ _/ _____ II 22 \___ _/ _____ III 22 \___ __/ _____ IV 26 \___ __/ _____ V 20 \___ __/ _____ Total 120 \____ _/ _____ Please read each question carefully and answer it completely and clearly. Complete Lewis structures are acceptable for answers unless you are given other specific instructions. Precision in drawing is an important skill in the communication of organic chemistry concepts. Double-check any three-dimensional representations to ensure you are implying an unequivocal direction of bonding. Do not forget to include important features such as nonbonding lone electron pairs and formal charges when appropriate. Individual point values are given in the corner of each answer space. The exam has 6 pages in addition to this cover page. A pK a table is on the last page.
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Name _______________________ Page 1 F.08.215E2 I. (30 points) Cyclic esters are called lactones. When compound A is treated with excess HBr, the intramolecular acylation reaction resulting in a 7-membered ring lactone takes place (Compound B ). Draw the structure of the expected uncharged, tetrahedral intermediate in this reaction, and the mechanism for its subsequent transformation, and show these in the central box below. Provide a step-wise, curved- arrow reaction mechanism for this entire transformation starting from the hydroxy acid structure ( A ), and giving B , through the intermediate. You may use H-B and B- for the acid and its conjugate base,
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F.08.215.E2K - Chemistry 215 Second Examination October 29,...

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