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Assignment

The document provides calculations for specific rotation based on enantiomeric excess (ee) for various mixtures. It includes examples involving cholesterol, isomers, cavicularin, and alanine, detailing the observed rotations and the resulting percentages of each component. The final answers indicate the composition and specific rotations for each case.

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matinsophy145
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4 views2 pages

Assignment

The document provides calculations for specific rotation based on enantiomeric excess (ee) for various mixtures. It includes examples involving cholesterol, isomers, cavicularin, and alanine, detailing the observed rotations and the resulting percentages of each component. The final answers indicate the composition and specific rotations for each case.

Uploaded by

matinsophy145
Copyright
© All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd

Key idea (don’t skip this):

Observed (or mixture) specific rotation depends on enantiomeric excess (ee).


rotation of pure enantiomerObserved rotation=(ee)×(rotation of pure enantiomer)
And:
ee=%major−%minor
Now—let’s do the work.

1. Cholesterol problem
Given:
• Observed rotation = –22.4°
• Pure cholesterol rotation = –32°
ee=−32−22.4=0.70=70%
So the mixture has 70% excess of cholesterol over its enantiomer.
Let:
• % cholesterol = x
• % enantiomer = 100−x
x−(100−x)=70 2x=170⇒x=85

✅ Answer
• 85% cholesterol
• 15% enantiomer

2. Mixture of (+) and (–) isomers


Given:
• Pure substance rotation = +78°
• Mixture: 75% (+) and 25% (–)
ee=75−25=50%=0.50 rotationObserved rotation=0.50×78=+39°

✅ Answer
• Specific rotation = +39°
3. Cavicularin mixture
Given:
• (+)-Cavicularin = +168.2°
• Mixture: 40% (+) and 60% (–)
Major is (–).
ee=60−40=20%=0.20 rotationObserved rotation=0.20×(−168.2)=−33.64°

✅ Answer
• Specific rotation = –33.6° (rounded)

4. Alanine enantiomers
Given:
• (S)-alanine = +8.5°
• Mixture: 80% S, 20% R
ee=80−20=60%=0.60 rotationObserved rotation=0.60×8.5=+5.1°

✅ Answer
• Specific rotation = +5.1°

Question Answer
1 85% cholesterol, 15% enantiomer
2 +39°
3 –33.6°
4 +5.1°

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