SCC Organic Chemistry Electrophilic Aromatic Substitution Questions

Organic Synthesis Experimental Activity: EAS ReactionWatch the following videos from the Second Semester Organic Chemistry Lab at Eastern
Kentucky University, U.S.
1. Provide the chemical reaction of the Electrophilic Aromatic Iodination reaction being
performed in this video. Include the structure of your predicted product.
2. An active electrophile is being generated in situ. Show the associated chemical equation.
Why is the active electrophile being called the “iodo cation”?
3. Focusing on the two directing groups attached to the aromatic ring in the organic
reactant, use resonance structures to explain the theory behind why you would expect the
product that you drew in Q#1.
4. Draw the full EAS mechanism for this reaction.
5. Explain the plan the instructor describes to verify the identity of the product.
6. Write the reaction procedure and fill in the following reaction table.
Amount mmol equivalents MP Concentration CAS# Density Safety Appearance
7. What is the purpose of the 10% sodium thiosulfate work-up step?
8. What is the purpose of the 10% HCl work-up step?
9. Calculate a % yield for the reaction.
10. Analyze the IR spectrum for diagnostic bands and to identify the substitution pattern of
the aromatic ring.
Note: this screenshot was taken from the video. If it is too difficult to see the values, take
another look at the video to see if that is clearer.
11. Describe the procedure and results for the Belstein test.

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