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Would you predict that the reaction of an acyl chloride (acid chloride) with an amine to...

  1. Would you predict that the reaction of an acyl chloride (acid chloride) with an amine to form an amide would be faster or slower that the reaction with an alkyl chloride with an amine to form a substituted amine? What evidence from this procedure can you use to answer this question?
  2. What product would be obtain if you reacted chloroacetyl chloride with methanol. Would you get different products if you ran this reaction in methanol which contained sodium methoxide? Please give structures for all expected products. If you expect different products if the methanol solution is basic give a brief description as to why this would be the expected result.
  3. Give the hydrolysis products expected for each of the analgesics shown on the first page (cocaine, lidocaine, and procaine). You can assume that the conditions are appropriate to hydrolyze all ester and amide groups and that neutral compounds (i.e. not the carboxylic acid or amine salts) can be recovered after an appropriate work-up.
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