b. Rank the indicated protons on the molecule below in order of acidity, indicat

Question

b. Rank the indicated protons on the molecule below in order of acidity, indicating which is least acidic and which is most acidic. Explain why in words and with pictures/other structures, if appropriate (using arguments based on relative charge stability). You do not need to draw a free energy versus reaction coordinate diagram.

b. Rank the indicated protons on the molecule below in order of acidity, indicating which is least acidic and which is most acidic. Explain why in words and with pictures/other structures, if appropriate (using arguments based on relative charge stability). You do not need to draw a free energy versus reaction coordinate diagram OH HS NH

Explanation / Answer

b > a > c

As the atom is more Electronegative then it is more acidic.

Sulphur is more electronegative than oxygen and oxygen is more electronegative than nitrogen so acidity decreases from S to O to N

Nitrogen is most effective at stabilizing a positive charge and least effective at stabilizing a negative charge

Sulfur is most effective at stabilizing a negative charge and least effective at stabilizing a positive charge

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