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Method Outline

Week 1:

  • Add reagents and reflux
  • Repeat

Week 2:

  • Analyze pheacetin through MP, IR, H NMR, and mass

  • Once again add reagents and reflux
  • Adjust the pH*
  • Add reagents and... reflux!

Phenacetin

Summary of Results

Introduction

  • Percent yield: 60%
  • MP: 123 (lit 134)
  • IR: good.
  • H NMR: good.

Week 3:

  • Analyze dulcin through MP, IR, H NMR, and mass

Dulcin

  • What is Acetaminophen?
  • What is Phenacetin?

*caused me headaches

  • Percent yield: 110%...
  • MP: 160 (lit 173 dulcin)
  • IR: bad.
  • H NMR: bad.

Objectives

Week 1:

  • Synthesize phenacetin from acetaminophen/Tylenol

Week 2:

  • Identify product phenacetin though spectra and MP before continuing the synthesis
  • Synthesize dulcin from phenacetin
  • What is Dulcin?

Week 3:

  • Identify dulcin through spectra and MP

nucleophilic

addition

amide

hydrolysis

Chemical Equations

William Ether

Synthesis

[Attempted] Synthesis of the Sweetener Dulcin from Acetaminophen

amide proton

what dulcin H NMR should

have looked like

para substituted

aromatic ring

Breanna Laurente

CHM 375E

next to

electronegative

atom (ethyloxy-)

next to unsaturated center

acetaminophen

water

next to

saturated center

dulcin

TMS

Experimental & Literature Spectra for Products Phenacetin and Dulcin

Dulcin (?)

Phenacetin

Sources

phenacetin

  • Goldsmith, R.H. 1987. “A Tale of Two Sweeteners,” J. Chem. Ed., 64(11):954-955.
  • Hill, J.W. 1988. “Using Chemical Principles to Encourage Critical Thinking in Consumer Chemistry,” J. Chem. Ed., 65(3):209.
  • PubChem Compound. Phenacetin. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=4754#x94
  • SciFinder Scholar:
  • Dulcin H NMR
  • Phenacetin H NMR
  • Sodium Bicarbonate H NMR
  • Spectral Database for Organic Compounds:
  • Dulcin IR
  • Phenacetin IR
  • Williams BD, Williams B, Rodino L. 2000. “Synthesis of the Sweetner Dulcin from the Analgesic Acetaminophen,” J. Chem. Ed., 77(3):357-358.
  • 3472: alcohol
  • 3281: secondary amine
  • 3131, 3073: alkene
  • 2927: Csp3-H

sodium bicarbonate IR

same peaks as experimental

COOH

broad stretch

2500-3500

C=O

1650

amide

1657

Synthesize dulcin from acetaminophen & identify through H NMR, IR, and MP

  • But was able to find what the final reaction solid was :)

Synthesize phenacetin from acetaminophen & identified through H NMR, IR, and MP.

Conclusions

Week 3

  • Impurities in the phenacetin H NMR tube

Week 2

  • pH adjustment
  • Use liquid sodium bicarbonate
  • Burning the reaction mixture
  • Phenacetin was positively identified the first time, but the reaction was not able to continue to dulcin due to this

Week 1

  • Not drying the product enough by using an oven/heat source
  • Thought drying in drawer would be sufficient

Possible Errors

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