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Chemistry 233 Exam_2B KEYFall 08

Chemistry 233 Exam_2B KEYFall 08 - Chemistry 233 Exam#2...

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Chemistry 233 Exam #2 Fall 2008 Name:___________________________ ID:______________________________ Please keep in mind that all of the work you submit is to be your’s alone! (1) 4 pts each Draw a structure which correctly represents the molecules named below. This question was flawed as you can probably tell _____________________________ 1,3-dimethylcyclohepta-1,3-diene _____________________________ (2 R ,5 S )-5-chloro-4-methyl-2-heptanamine H 2 N H Cl H 4 position is ignored _____________________________ Provide a name accurately describes each of the molecules shown below. Where stereochemistry is indicated be certain to show it.
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H F H 3 C H O Br (S or R) (No R or S) H 3 C HO H 3 C (2R,4S)-4-bromo-4-fluoro-2- methoxybutane 5-ethyl-2-methyl-3-heptyne trans-2-methylcyclohexanol (2) 5 pts each. In the reactions shown below draw the structure of the expected product.
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O O and ( 2 ) HO (-) / H 2 O H 2 / Pd-C dichloromethane ( 1 ) RCO 3 H t-ButylO (-) K (+) CHBr 3 Br 2 / CH 3 CH 2 OH Cl 2 H 3 C ( 1 ) Hg(OAc) 2 / THF-H 2 O) ( 2 ) H 2 O 2 / HO (-) CH 2 N 2 OH HO OEt Br Br Br H 3 C Cl Cl + isomer
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HBr (anhydrous) (1) HB(isoamyl) 2 (1) Ozone (2) Zn / H 2 O 1 equiv.
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