Rank the acidity of the red bolded hydrogen on the following molecules from lowest to highest pka. Remember, a low pKa is more acidic than a high pka. Compound 1 OH S-OH Compound 3 O Compound 2 P-OH OH N-H H Compound 4 4

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Chapter1: Chemical Foundations
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Rank the acidity of the red bolded hydrogen on the following
molecules from lowest to highest pka.
Remember, a low pKa is more acidic than a high pka.
Compound 1
Question 23 of 40
Compound 3
OH
-OH
lot of
A) 3< 4 < 1<2
Compound 2
B) 4 < 1 < 3 < 2
N-H
Compound 4
Submit
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Transcribed Image Text:52°F Sunny Rank the acidity of the red bolded hydrogen on the following molecules from lowest to highest pka. Remember, a low pKa is more acidic than a high pka. Compound 1 Question 23 of 40 Compound 3 OH -OH lot of A) 3< 4 < 1<2 Compound 2 B) 4 < 1 < 3 < 2 N-H Compound 4 Submit Q Search
Expert Solution
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The acidity of a molecule's hydrogen atom (H) depends on the atom's identity or the functional group it is attached to. When H is attached to an atom or functional group that can stabilize the negative charge that results from deprotonation, the H atom is more acidic.

Compound 3 is the most acidic H atom as it is attached to a resonance-stabilized structure which is more acidic because the negative charge is delocalized over multiple atoms.

Compound 4 has a hydrogen atom attached to the resonance-stabilized structure.

H atom attached to the N atom is least acidic due to H atom attached to the least electronegative atom nitrogen (N), the electron density around the H atom is higher, making it less acidic.

 

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