2311quiz3 2009 - Chemistry 2311, Spring 2009 Student Name _...

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Chemistry 2311, Spring 2009 Student Name ______________________________ Last Name of TA _______________ Quiz #3B (50 pts) 1. The nitration of anisole is reported to give a mixture of o , p , and meta products as indicated below. OCH 3 HNO 3 H 2 SO 4 OCH 3 NO 2 + OCH 3 OCH 3 + NO 2 NO 2 bp 154 o C bp 273 o C mp 9.5 o C bp 263 o C mp 36-38 o C bp 260 o C mp 51-53 o C A-31% B-2% C-67% a. Match the products to the expected approximate aromatic 1 H NMRs given below: (d = doublet, t = triplet) 6 pts Circle one δ 7.38 (dd), 7.45 (t), 7.66 (t), 7.82 (dd) A B C δ 6.91 (d), 8.15 (d) A B C δ 6.91 (dd), 7.73 (ddd), 7.62 (ddd), 8.15 (dd) A B C b. What affect does the nitro group have on the chemical shift of Hs ortho to it? Circle one. 2 pts Downfield chemical shift from 7.36 ppm Upfield chemical shift from 7.36 ppm c. A typical proton-proton coupling constant for aromatic hydrogens that are meta to each other is: 2 pts 6 to 9 Hz 1 to 3 Hz 0-1 Hz d. The three products, A, B, and C can be analyzed by Gas Chromatography to determine their ratio. Based on the boiling point trend of the three compounds, which compound would have the shortest retention time on the GC? 2 pts
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2311quiz3 2009 - Chemistry 2311, Spring 2009 Student Name _...

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