14C_w11_e01

14C_w11_e01 - Chemistry 14C Winter 2011 Exam 1 Page 1...

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Chemistry 14C Winter 2011 Exam 1 Page 1 Page 1 score = Hydroxyzine is an antihistamine that works by antagonizing (blocking) the H 1 receptor. It also has antiemetic and mild anxiolytic (anti-anxiety) properties. Cetirizine, a major human metabolite of hydroxyzine, also has antihistamine properties. (These two drugs illustrate nicely the concept that similar molecules often have somewhat similar biological properties.) Questions 1–11 concern the structures of these antihistamines. N N Cl O OH metabolism N N Cl O O OH Question 6 Hydroxyzine Cetirizine 1. (3) Write the molecular formula (i.e., C 3 H 60 ) of hydroxyzine. 2. (5) Complete this sentence by writing functional group names in the blanks: Metabolism converts the _________________ of hydroxyzine into the _________________ of cetirizine, but the _________________, _________________, and_________________ are not changed. 3. (2) Circle the figure that best describes the O–H bond of hydroxyzine: δ + O–H δ - δ - O–H δ + + O–H - - O–H + None of these 4. (2) In its most stable state how many rings of cetirizine are in a chair conformation? Circle one: 0 1 2 3 4 5. (4) Give numbers: Cetirizine has _______________ lone pair(s) and _______________ stereocenter(s). 6. (2) The certirizine C–N–C bond angle indicated on the structure above is closest to (circle one): 50 o 60 o 70 o 80 o 90 o 100 o 110 o 120 o 130 o 140 o 150 o 160 o 170 o 180 o 7. (2) Add hydrogen atoms as necessary to complete the following drawing of cetirizine so that all its stereocenters have the S configuration. If this is not possible, write “not possible.” N N Cl O O OH 8. (3) By adding, subtracting, or transmuting no more than three atoms , redraw the structure of cetirizine so that it
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14C_w11_e01 - Chemistry 14C Winter 2011 Exam 1 Page 1...

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