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The \(\mathrm{p} K_{\mathrm{a}}\) of acetone, \(\mathrm{CH}_{3} \mathrm{COCH}_{3}\), is 19.3 . Which of the following bases is strong enough to deprotonate acetone? (a) \(\mathrm{KOH}\left(\mathrm{p} K_{\mathrm{a}}\right.\) of \(\mathrm{H}_{2} \mathrm{O}=15.7\) ) (b) \(\mathrm{Na}^{+}-\mathrm{C} \equiv \mathrm{CH}\left(\mathrm{p} K_{\mathrm{a}}\right.\) of \(\left.\mathrm{C}_{2} \mathrm{H}_{2}=25\right)\) (c) \(\mathrm{NaHCO}_{3}\left(\mathrm{p} K_{\mathrm{a}}\right.\) of \(\left.\mathrm{H}_{2} \mathrm{CO}_{3}=6.4\right)\) (d) \(\mathrm{NaOCH}_{3}\left(\mathrm{p} K_{\mathrm{a}}\right.\) of \(\mathrm{CH}_{3} \mathrm{OH}=15.6\) )

Short Answer

Expert verified
Na鈦-C鈮H is strong enough to deprotonate acetone.

Step by step solution

01

Understanding Deprotonation

Deprotonation is the removal of a proton (H鈦) from an acid. A base can deprotonate an acid if it is stronger than the conjugate base of the acid.
02

Analyzing Acid-Base Strength with pKa Values

A stronger base will have a weaker conjugate acid, which is indicated by a higher pKa value. Therefore, to deprotonate acetone, a base must have an accompanying acid with a pKa higher than 19.3.
03

Comparing pKa Values

- For KOH, the pKa of H2O is 15.7, which is lower than acetone's pKa of 19.3. - For Na鈦-C鈮H, the pKa of C2H2 is 25, which is higher. - For NaHCO3, the pKa of H2CO3 is 6.4, which is lower. - For NaOCH3, the pKa of CH3OH is 15.6, which is lower than 19.3.
04

Identifying the Suitable Base

The only base with a conjugate acid having a pKa higher than 19.3 is Na鈦-C鈮H, as the pKa of C2H2 is 25. This indicates that Na鈦-C鈮H is strong enough to deprotonate acetone.

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Acid-Base Reactions
Acid-base reactions are fundamental chemical processes where an acid donates a proton ( H 鈦) to a base. This proton transfer results in the formation of a conjugate acid-base pair. The original base becomes the conjugate acid after gaining a proton, while the original acid becomes the conjugate base after losing a proton.
For example, when hydrochloric acid ( HCl) reacts with water ( H 鈧侽), the HCl donates a proton to H 鈧侽, forming hydronium ( H 鈧僌鈦) and chloride ( Cl鈦) ions.
In this reaction:
  • HCl acts as the acid.
  • H 鈧侽 acts as the base.
  • H 鈧僌鈦 is the conjugate acid.
  • Cl鈦 is the conjugate base.
The strength of acids and bases can be compared using their pKa values, which indicate their tendency to donate or accept protons. Understanding these reactions helps in predicting the behavior of chemical species in a mixture.
Deprotonation
Deprotonation is a process where a proton ( H 鈦) is removed from a molecule, transforming it into its conjugate base. This step is critical in many chemical reactions, especially in organic chemistry.
To deprotonate a substance, the base performing the deprotonation must be stronger than the conjugate base that forms.
The relative strength of a base can be determined by the pKa value of its conjugate acid. A higher pKa value means a weaker acid, thereby implying that the base form is stronger.
In the context of acetone ( CH 鈧僀OCH 鈧), a base that can deprotonate it must have a conjugate acid with a pKa higher than 19.3. Thus, selecting the right base depends on comparing these pKa values.
Acetone
Acetone, with the chemical formula CH 鈧僀OCH 鈧, is a ketone widely used as a solvent and an intermediate in organic synthesis. Its deprotonation involves removing a proton from one of the methyl groups, creating a resonance-stabilized enolate ion.
The pKa of acetone is 19.3, indicating it is relatively weak as an acid. It requires a very strong base to be deprotonated.
In practical terms, this means only highly stable conjugate acids, which possess pKa values well above 19.3, can successfully pull a proton off acetone. Understanding acetone's reactivity is crucial in synthetic applications where control over the enolate formation is needed.
Conjugate Acid-Base Pairs
Conjugate acid-base pairs play a vital role in understanding chemical equilibria. When an acid donates a proton, it forms its conjugate base, and when a base accepts a proton, it forms its conjugate acid.
This relationship is crucial in determining the outcome of acid-base reactions. The strength of an acid can be measured by observing the stability of its conjugate base.
In practical terms:
  • A strong acid has a weak conjugate base.
  • A weak acid has a strong conjugate base.
This inverse relationship helps chemists select appropriate bases for deprotonation reactions. For acetone, represented by CH 鈧僀OCH 鈧, understanding its conjugate base helps determine the conditions needed for reactions involving it, such as which bases are strong enough to cause deprotonation. Recognizing these pairs facilitates better predictions and control over chemical processes.

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