Interpret the NMR results in terms of purity. What should a chemist do to improve the yield or purity of the product?     Discuss the key parts of the NMR for the starting material and pure product.  Focus on the peaks that show up after 3 ppm.  For the starting material, discuss what those 2 peaks (around 3.5 ppm and 4.7 ppm) correspond to in the structure of cyclohexanol.  For the pure product, discuss why those 2 peaks are missing, and there is a new peak for 2H at around 5.6 ppm.  Then, discuss the NMR for your actual product from the reaction.  Does it contain pure product?  If not, what else is there?  How do you know this based on the NMR? Based on your understanding of the reaction and LeChatelier’s principle, how can you improve the reaction yield?  How can you better purify the reaction product?

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
ChapterL4: Proton (1h) Nmr Spectroscopy
Section: Chapter Questions
Problem 15E
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  • Interpret the NMR results in terms of purity. What should a chemist do to improve the yield or purity of the product?

 

 

Discuss the key parts of the NMR for the starting material and pure product.  Focus on the peaks that show up after 3 ppm.  For the starting material, discuss what those 2 peaks (around 3.5 ppm and 4.7 ppm) correspond to in the structure of cyclohexanol.  For the pure product, discuss why those 2 peaks are missing, and there is a new peak for 2H at around 5.6 ppm. 

Then, discuss the NMR for your actual product from the reaction.  Does it contain pure product?  If not, what else is there?  How do you know this based on the NMR?

Based on your understanding of the reaction and LeChatelier’s principle, how can you improve the reaction yield?  How can you better purify the reaction product?

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