Acidic Hydrogens in Aspartame: Which Ones Are Most Acidic and Why?

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SUMMARY

The discussion focuses on identifying the two most acidic hydrogens in aspartame, specifically the hydrogen on the carbon connected to the NH group and the hydrogen on the carboxylic acid (COOH) group. The reasoning emphasizes the importance of resonance stabilization and electronegativity in determining acidity. Participants are encouraged to draw diagrams to visualize charge stabilization and compare electronegativities of the involved atoms.

PREREQUISITES
  • Understanding of organic chemistry concepts, particularly acidity and resonance.
  • Familiarity with molecular structures and functional groups, specifically carboxylic acids and amines.
  • Knowledge of electronegativity and its role in chemical reactivity.
  • Ability to interpret and analyze molecular diagrams.
NEXT STEPS
  • Research the concept of resonance stabilization in organic molecules.
  • Study the acidity of carboxylic acids compared to amines.
  • Learn about electronegativity trends in the periodic table.
  • Explore molecular visualization tools to better understand molecular structures.
USEFUL FOR

Chemistry students, organic chemists, and anyone interested in understanding the acidity of organic compounds, particularly in the context of aspartame and similar molecules.

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Homework Statement



http://en.wikipedia.org/wiki/File:Aspart…

What are the 2 most acidic hydrogens in this molecule?and why?

Homework Equations





The Attempt at a Solution



I narrowed it to:

1) the H on the carbon wedge connected to NH
2) the H on the carboxylic acid COOH
3) the H on the NH
 
Last edited by a moderator:
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Acidic hydrogens are going to be attached to atoms that can stabilize a charge the best through resonance, so draw some diagrams, and look at electronegativity, comparing them...
 

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