mcI04e1 - MEDICINAL CHEMISTRY I EXAM #1 October 1, 2004...

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MEDICINAL CHEMISTRY I EXAM #1 October 1, 2004 Name SECTION A. Answer each question in this section by writing the letter corresponding to the best answer on the line provided (2 points each; 50 points total) 1. The compound shown below: N I Is a base II Is 3H-pyrrole III Uses the lone pair of electrons on the nitrogen to make the ring aromatic a) I only b) III only c) I and II only d) II and III only e) I, II, and III Answer 2. The functional group in the compound illustrated below: S N O O CH 3 I Is a sulfonamide II Is an acid with pKa = 7 III Contains a nitrogen that functions as a base a) I only b) III only c) I and II only d) II and III only e) I, II, and III Answer 3. The structures illustrated below: O CO 2 Et OH CO 2 Et A B I Are resonance structures II Are acids with pKa =9 III Are tautomers a) I only b) III only c) I and II only d) II and III only e) I, II, and III Answer
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2 4. The drug illustrated below: H 2 N C O O CH 2 CH 2 N CH 3 CH 3 I Is 90.9% ionized at pH 8 II Contains a ketone functional group III Is 0.01% ionized at pH 8 a) I only b) III only c) I and II only d) II and III only e) I, II, and III Answer 5. The compound illustrated below: N O I Is 1-oxazoline II Is 3-oxazoline III Contains an imine functional group a) I only b) III only c) I and II only d) II and III only e) I, II, and III Answer 6. For the compounds shown below: NHCCH 3 O NHCCH 3 O H 3 CO A B I Compound A has a lower pK b than Compound B II Compound B has a lower pK b than Compound A III Compound B has a lower log P than Compound A a) I only b) III only c) I and II only d) II and III only e) I, II, and III Answer
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3 7. For the compounds illustrated below: CH 3 H CH 3 H CH 3 H H CH 3 A B I Compound A is trans -1,2-dimethyl- cyclohexane II Compound A is higher in energy than Compound B III Compound A is lower in energy than Compound B a) I only b) III only c) I and II only d) II and III only e) I, II, and III Answer 8. The drug illustrated below: O N CH 3 OH O HO 1 2 3 4 5 6 I Has a conjugate base that has pK b = 5 II Has (R)-stereochemistry at the 5-position III Contains an ester functional group a) I only b) III only c) I and II only d) II and III only e) I, II, and III Answer 9. The compound illustrated below: HN I Is aromatic II Is antiaromatic III Is a base with pK b = 10 a) I only b) III only c) I and II only d) II and III only e) I, II, and III Answer
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4 10. For the two compounds shown below: OH C OH H 3 C N A B I Compound B has a lower pK a than Compound A II Compound A is more acidic than Compound B III Compound A has a lower log P than
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mcI04e1 - MEDICINAL CHEMISTRY I EXAM #1 October 1, 2004...

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