Provide a mechanism, including intermediates, for the following procedure  Charge a 100 mL round-bottom flask with 40mL of 2 M pentanolic KOH solution, 5.0g of PET shavings, and a stirring bar. Heat the mixture to a gentle reflux and keep it refluxing for 2 hours with continuous stirring. Cool the reaction mixture and add 25 mL of water to dissolve the white terephthalate salt. Filter the solution using a Büchner funnel to remove undissolved PET. Transfer the filtrate to a separatory funnel and remove the bottom aqueous layer. Wash the pentanolic layer with an additional 25 mL of water, remove the bottom layer, and combine with the other aqueous layers. Add 2 M HCl to the aqueous layer while stirring until a precipitate that does not dissolve forms. Add the same volume of HCl again (approximately 30 mL or more) to fully protonate the compound. Collect the solid by suction filtration and air-dry it to obtain 4.138 g with a melting point above 400 °C. Set aside 0.5-1 g of the sample for PXRD analysis.

EBK A SMALL SCALE APPROACH TO ORGANIC L
4th Edition
ISBN:9781305446021
Author:Lampman
Publisher:Lampman
Chapter12: Isopentyl Acetate (banana Oil)
Section: Chapter Questions
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Provide a mechanism, including intermediates, for the following procedure 

  1. Charge a 100 mL round-bottom flask with 40mL of 2 M pentanolic KOH solution, 5.0g of PET shavings, and a stirring bar.
  2. Heat the mixture to a gentle reflux and keep it refluxing for 2 hours with continuous stirring.
  3. Cool the reaction mixture and add 25 mL of water to dissolve the white terephthalate salt.
  4. Filter the solution using a Büchner funnel to remove undissolved PET.
  5. Transfer the filtrate to a separatory funnel and remove the bottom aqueous layer.
  6. Wash the pentanolic layer with an additional 25 mL of water, remove the bottom layer, and combine with the other aqueous layers.
  7. Add 2 M HCl to the aqueous layer while stirring until a precipitate that does not dissolve forms.
  8. Add the same volume of HCl again (approximately 30 mL or more) to fully protonate the compound.
  9. Collect the solid by suction filtration and air-dry it to obtain 4.138 g with a melting point above 400 °C.
  10. Set aside 0.5-1 g of the sample for PXRD analysis.
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