mcI06e1 - MEDICINAL CHEMISTRY I EXAM #1 September 29, 2006...

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MEDICINAL CHEMISTRY I EXAM #1 September 29, 2006 N a m e 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 3,4-dihydroquinoline II Has a conjugate acid form with pK a = 4 III Is 3,4-dihydroisoquinoline 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: NH S O O I Is an amine II Is a sulfone III Is a sulfonamide a) I only b) III only c) I and II only d) II and III only e) I, II, and III Answer 3. For the structures illustrated below: CH 3 H 3 C H 3 C H H H CH 3 CH 3 CH 3 H H H A B I Structure A is 1,2,4-trimethylcyclohexane II Structure B is higher in energy than structure A III The methyl groups at the 1- and 2-position of structure A are cis - to one another a) I only b) III only c) I and II only d) II and III only e) I, II, and III Answer 1
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2 4. The compound illustrated below: N O O CH 3 CH 2 3 2 I Is 50% ionized at pH 9 II Is the conjugate base of 3,3-diethyl-1,2,3,6-tetrahydropyridine- 2,6-dione III Is 100% ionized at all pH values 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: O O I Is vinyl propionate II Is ethyl 3-propenoate III Is allyl propionate 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: N N O I Is antiaromatic II Is aromatic III Is 2H-1,4,6-oxdiazocine a) I only b) III only c) I and II only d) II and III only e) I, II, and III Answer 7. For the compounds illustrated below: NH 3 H 3 CO NH 3 S O O H 3 C A B I Compound A is a stronger base than compound B II Compound A has a larger pK a than compound B III Compound B is a stronger acid 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 8. The drug illustrated below: HN CH 3 Cl Cl H H I Has two chiral centers with S-stereochemistry II Has cis -1,4- substituents on the 1,2,3,4-tetrahydronaphthalene ring III Is a base with pK b = 5 a) I only b) III only c) I and II only d) II and III only e) I, II, and III Answer 9. In the compound illustrated below: C N I The lone pair is contained in an sp-hybrid orbital II The geometry at the carbon attached to the benzene ring is linear III The lone pair is in the same plane as the benzene ring a) I only b) III only c) I and II only d) II and III only e) I, II, and III Answer 10.
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This note was uploaded on 04/14/2009 for the course 663 701 taught by Professor Arnold,e. during the Spring '09 term at Rutgers.

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mcI06e1 - MEDICINAL CHEMISTRY I EXAM #1 September 29, 2006...

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