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Experiment 20: Reaction of Iodoethane with Sodium Saccharin, an Ambident Nucleophile Postlab Assignment

Includes the following questions and answers: 1. Under which class of substitution reaction (SN1 or SN2) does this reaction appear to fall? Explain 2. Considering the two resonance structures of the conjugate base of saccharin, which atom (N or O) bears more of the negative charge? Explain why? 3. What will be the possible effect on your results if you used water as the reaction solvent instead of dimethylformamide (DMF)? 4. Most compounds that contain N-H bonds are basic but saccharin is acidic. Explain using resonance structures. 5. Show the mechanism (with arrow pushing) of the reaction that was carried out in this experiment.

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Course code
CHEM225
Summarized whole book?
No
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Experiment 20
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July 25, 2018
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2017/2018
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Book Title
Operational Organic Chemistry
Author(s)
John W. Lehman
Year
2009
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