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Homework Help: Reaction Question

  1. Feb 27, 2010 #1
    1. The problem statement, all variables and given/known data

    Given the following reactions, determine the moles of product that should be produced. If sulfuric acid were not used in the third equation, would water be a good recrystallization solvent? What if choloroacetic acid was used instead of the sodium salt? Finally what evidence would an NMR provide to reveal the substitution reaction took place?

    mol NaOH : 0.0025
    mol o-cresol: 0.0025
    mol sodium chloroacetate: 0.0025

    1 mL of 10% H2SO4

    http://img402.imageshack.us/img402/7127/chem262lrxn.png [Broken]

    2. Relevant equations

    chemistry duhdhdhdh

    3. The attempt at a solution

    For the first question, everything is in a 1:1:1 molar ratio; however, the limiting reagent in the final step is unclear to me because in the actual experiment, we used 1 mL of 10% sulfuric acid. This corresponds to 0.001 mol of acid, vs 0.0025 mol of NaOH, o-cresol, and sodium chloroacetate. Since the percent yield is based on the limiting reagent, I'd expect only 0.001 mol of product to be produced. Am I correct in assuming the final moles of product yielded are limited by the mols of acid present?

    The second question, I don't know. Without an acid to protonate the salt wouldn't the water serve the same purpose? Still allowing it to be a good recrystallization solvent?

    I feel the chloroacetic acid's alcohol hydrogen would be plucked off by the oxygen in the phenolate anion instead of it attacking the carbon adjacent to the chloride...

    Finally, I have no idea where to begin in regards to NMR at all.
    Last edited by a moderator: May 4, 2017
  2. jcsd
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