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mcI07e1 - 1 MEDICINAL CHEMISTRY I EXAM#1 Name SECTION A...

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1 MEDICINAL CHEMISTRY I EXAM #1 September 28, 2007 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: H N O O I Is a cyclic urea II Is piperidine-2,5-dione III Is a cyclic imide a) I only b) III only c) I and II only d) II and III only e) I, II, and III Answer 2. The compound illustrated below: CH 3 CH 3 H 3 C H H H I Has cis -1,4-dimethyl groups II Has trans -1,2-dimethyl groups III Is drawn in its lowest energy conformation 3. For the structures illustrated below: OH H 3 C OH NC A B I Compound A has a larger pK a than compound B II Compound A has a higher log P than compound B III The K a for Compound B is larger than the K a for Compound A
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2 4. The compound illustrated below: N O I Is 1-Benzyl-4-benzoylisoquinoline II Is 1-Benzoyl-4-benzylisoquinoline III Is 4-Benzoylbenzo[a]isoquinoline 5. The compound illustrated below: N O I Is aromatic II Has the lone pair of electrons (on the nitrogen), in the plane of the ring III Is non-aromatic a) I only b) III only c) I and II only d) II and III only e) I, II, and III Answer 6. T he compound shown below: O H 3 C CH 3 I Is 2H-2,7-dimethyl-5,6,7,10- tetrahydrooxecine II Has two alkenes that have (E)- stereochemistry III Is antiaromatic
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3 7. For the compounds illustrated below: CH 3 H 3 C CH 3 OH H CH 3 H 3 C CH 3 H HO A B I Compound A has four chiral centers II Compound A is a diastereomer of Compound B III Compound B is the enantiomer of Compound A 8. The compound illustrated below: S N CH 3 I Is 10-methylphenothiazine II Has a conjugate acid with a pK a of 2 III Is 5-methylphenothiazine
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