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Answer: In each compound below, two protons are clearly

Chapter 3, Problem 3.25

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QUESTION:

In each compound below, two protons are clearly identified. Determine which of the two protons is more acidic: (a) OH H (b) O O H H (c) NH2 HO O N (d) N H H (e) N N H H (f) HO SH O S (g) N H H (h) O OH HO (i) N S O O O H O

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QUESTION:

In each compound below, two protons are clearly identified. Determine which of the two protons is more acidic: (a) OH H (b) O O H H (c) NH2 HO O N (d) N H H (e) N N H H (f) HO SH O S (g) N H H (h) O OH HO (i) N S O O O H O

ANSWER:

Step 1 of 9

a.  The more acidic proton will create a more stable conjugate base when removed. Here, the red proton creates a conjugate base with a negative charge stabilized by a heteroatom as opposed to only carbon, so it is more acidic.

     

 

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