mcI07e1 - 1 MEDICINAL CHEMISTRY I EXAM #1 September 28,...

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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 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: 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 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 compound illustrated below: N O I Is 1-Benzyl-4-benzoylisoquinoline II Is 1-Benzoyl-4-benzylisoquinoline III Is 4-Benzoylbenzo[a]isoquinoline 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 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 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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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 a) I only b) III only c) I and II only d) II and III only e) I, II, and III Answer 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 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: N O I Is 50% ionized at pH 12 II Is the conjugate base of 1,3,4,5-tetrahydro-2H- benzo[b]azepin-2-one III Is 100% ionized at pH 7 a) I only b) III only c) I and II only d) II and III only e) I, II, and III Answer 10. Consider the two structures shown below: NHCH 3 F 3 C NHCH 3 H 3 C A B I Compound A has a lower log P than Compound B II Compound B is a stronger base than Compound A III Compound A has a higher log P than
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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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mcI07e1 - 1 MEDICINAL CHEMISTRY I EXAM #1 September 28,...

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