Ch06_InClassProblemsExamples

Ch06_InClassProblemsExamples - ] D A 1.00-g sample is...

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1 Enantiomers Enantiomers 2-Butanol has one chiral center here are four different representations for one enantiomer using (4) as a model, here are two different representations for the enantiomer of (4) H 3 C OH CH 2 CH 3 H (1) H 3 C OH CH 2 CH 3 H (2) OH H (3) OH (4) OH OH Enantiomers Enantiomers 2-Chlorobutane C H 3 CHCH 2 C H 3 C l C l H C l H 3-chloropentane
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2 Enantiomers Enantiomers 3-Chlorocyclohexene Cl Cl chlorocyclohexane Enantiomers Enantiomers A nitrogen chiral center N C H 2 C H 3 H 3 C N C H 3 C H 3 C H 2 A pair of enantiomers + +
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3 Problem Problem Which structure is different from the other three? A B C D F H H 3 C Br Br H F CH 3 F Br H CH 3 CH 3 H F Br Naming Chiral Centers Naming Chiral Centers ( R )-3-Chlorocyclohexene ( )-Mevalonic acid 2 3 R 1 2 3 1 R Cl H HO OH O HO CH 3 1 2 3 4 1 2 3 4
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4 Problem Problem ( R ) ( S ) ( ) ( ) ( ) ( ) ( ) ( ) Which structure is different from the other three? A B C D Br H H 3 C F CH 3 Br F H Br F H CH 3 Br H H 3 C F OH CH 2 CH 3 H OH CH 3 H CH 2 CH 3 HO H H H CH 3 H HO CH 3 H H A B C D Cl Cl H 3 C OH H 3 C Cl O CH 3 CH 3 H CH 3 Cl Cl Chiral/Achiral/Meso Chiral/Achiral/Meso ? * * σ * * σ * * σ σ H 3 C Cl * *
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5 Enantiomers/Diastereomers/Same Enantiomers/Diastereomers/Same ? Cl CH 3 Cl CH 3 H H vs Cl CH 3 enantiomers Br OH same CH 3 Br H H OH H 3 C Br vs OH Calculate [ Calculate [
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Unformatted text preview: ] D A 1.00-g sample is dissolved in 20.0 mL ethanol. 5.00 mL of this solution is placed in a 20.0-cm polarimeter tube at 25 C. The observed rotation is 1.25 counterclockwise. [ ] D 25 = -12.5 6 Enantiomeric Excess Enantiomeric Excess Example: Example: a commercial synthesis of naproxen, a nonsteroidal anti-inammatory drug (NSAID), gives the S enantiomer in 97% ee Calculate the percentages of the R and enantiomers in this mixture 1.5/98.5 % 1.5/98.5 % H 3 CO COOH CH 3 ( S )-Naproxen Optical Optical Purity Purity Example: Example: The specific rotation of ( S )-2-iodobutane is +15.90 . Determine the % composition of a mixture of ( R )-and ( S )-2-iodobutane if the specific rotation of the mixture is -3.18 . I + I 40% 60%...
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This note was uploaded on 12/09/2010 for the course CHM 265 taught by Professor Savinov during the Fall '10 term at Purdue University-West Lafayette.

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Ch06_InClassProblemsExamples - ] D A 1.00-g sample is...

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