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Strong Base Comparison: H?S?, CH?O?, CH?OH, Cl?, CH?COO?, CH?CHClCOO

Chapter 2, Problem 48P

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QUESTION:

Which is a stronger base?

a. \(\mathrm{HS}^{-} \text {or } \mathrm{HO}^{-}\)

b. \(\mathrm{CH}_{3} \mathrm{O}^{-} \text {or } \mathrm{CH}_{3} \mathrm{NH}^{-}\)

c. \(\mathrm{CH}_{3} \mathrm{OH} \text { or } \mathrm{CH}_{3} \mathrm{O}^{-}\)

d. \(\mathrm{Cl}^{-} \text {or } \mathrm{Br}^{-}\)

e. \(\mathrm{CH}_{3} \mathrm{COO}^{-} \text {or } \mathrm{CF}_{3} \mathrm{COO}^{-}\)

f. \(\mathrm{CH}_{3} \mathrm{CHClCOO}^{-} \text {or } \mathrm{CH}_{3} \mathrm{CHBrCOO}^{-}\)

Questions & Answers

QUESTION:

Which is a stronger base?

a. \(\mathrm{HS}^{-} \text {or } \mathrm{HO}^{-}\)

b. \(\mathrm{CH}_{3} \mathrm{O}^{-} \text {or } \mathrm{CH}_{3} \mathrm{NH}^{-}\)

c. \(\mathrm{CH}_{3} \mathrm{OH} \text { or } \mathrm{CH}_{3} \mathrm{O}^{-}\)

d. \(\mathrm{Cl}^{-} \text {or } \mathrm{Br}^{-}\)

e. \(\mathrm{CH}_{3} \mathrm{COO}^{-} \text {or } \mathrm{CF}_{3} \mathrm{COO}^{-}\)

f. \(\mathrm{CH}_{3} \mathrm{CHClCOO}^{-} \text {or } \mathrm{CH}_{3} \mathrm{CHBrCOO}^{-}\)

ANSWER:

Step 1 of 6

Here we have to find out which is stronger base among the given molecules. It is known that the relative acidity depends on the following two factors:

     1.  Atomic size

     2.  A Stronger base has weaker conjugate acid.

a.  \(\mathrm{HS}^{-} \text {or } \mathrm{HO}^{-}\)

Here the bases \(\mathrm{HS}^{-} \text {or } \mathrm{HO}^{-}\) are formed from its conjugate acid \mathrm{H}_2\mathrm{S} and \(\mathrm{H}_{2} \mathrm{O}\). Here \mathrm{H}_2\mathrm{S} is the stronger acid than that of  \(\mathrm{H}_{2} \mathrm{O}\) due to the presence of S-atom, which has big atomic size than O-atom.

The conjugate base of the strong acid is less basic, thus \(\mathrm{HO}^{-}\) is the stronger base than \(\mathrm{HS}^{-}\).

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Strong Base Comparison: H?S?, CH?O?, CH?OH, Cl?, CH?COO?, CH?CHClCOO
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Explore the reactivity of different bases in this chemistry comparison. We'll analyze the strength of H?S?, CH?O?, CH?OH, Cl?, CH?COO?, and CH?CHClCOO? in various reactions.


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