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    Aromatic Imide Formation: Synthesis of N-Phenylmaleimide

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    1. The second step in the reaction to from the imide is much slower than that of the first stage (formation of the acid amide). Explain.

    2) Phthalimide has a Ka = 5 x 10^-9. Write an equation for the reaction of phthalimide with potassium amide (a strong base) in N,N dimethylformamide (DMF) solvent. Name the product. See attachment 1 for more information.

    3) Predict Which of the following species is most acidic? Phthalimide (see attachment 1) or Benzamide (see Attachment 2)? Explain.

    4) The phthalimide anion is a strong nucleophile. It can react easiest with primary alkyl halides to form substituted phthalimides.

    Phthalimide (see attachment #1), K+(this is next to a N- in Phthalimide) +Ch3CH2BR ---> Phthalimide (The N is attached to CH2CH3) + KBr.

    Suggest a suitable mechanism for this reaction.

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    Solution Summary

    This solution discusses reactions around phthalimide.