Which of the following bases is most appropriate to deprotonate (acetic acid)?
A
(ammonia)
B
(sodium hydroxide)
C
(sodium hydride)
D
(sodium carbonate)
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1
Identify the acidity of acetic acid (CH\_3COOH) by considering its pKa value, which is approximately 4.76. This tells us how easily it donates a proton (H\^+).
Compare the strength of the bases given by looking at the conjugate acid pKa values. A base can deprotonate an acid if its conjugate acid has a higher pKa (weaker acid) than the acid being deprotonated.
List the conjugate acids and their approximate pKa values: ammonia (NH\_4\^+, pKa ~ 9.25), water (H\_2O, pKa ~ 15.7, related to NaOH), hydrogen gas (H\_2, pKa ~ 35, related to NaH), and bicarbonate (H\_2CO\_3, pKa ~ 6.3, related to Na\_2CO\_3).
Determine which base is strong enough to deprotonate acetic acid by selecting the base whose conjugate acid has a pKa significantly higher than 4.76, indicating it is a weaker acid and thus the base is stronger.
Conclude that sodium hydride (NaH) is the most appropriate base because its conjugate acid, hydrogen gas (H\_2), has a very high pKa, making NaH a very strong base capable of deprotonating acetic acid effectively.