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Chemguide: Support for CIE A level Chemistry Learning outcome 32: Hydroxy compounds 32.2: Phenol Learning outcomes 32.2.3 and 32.2.4 These statements deal with the acidity of phenol. Statement 32.2.3 talks about the acidity of phenol itself, and 32.2.4 compares it with water and ethanol. You should read the page explaining the acidity of organic acids down to and including the brief section on ethanol. This page also talks about the acidity of carboxylic acids. Although there is no mention of them in this statement, you will need to know about this eventually in Section 33. For the moment, read the bits about ethanoic acid, but don't continue into the section about variations in acid strengths between different carboxylic acids. Once you have finished reading the bits of this page I have suggested, you should know why phenol is more acidic than ethanol, but nothing like as acidic as ethanoic acid. The page doesn't, however, mention the acidity of water. In fact, the equilibrium here is exactly the same as all the other ones you have looked at. All I have done in the following equation is to replace the X in an equation on the page you have just read by an H.
Again, the extent of this ionisation depends on the stability of the hydroxide ion formed. And this is very similar to the ion formed when an alcohol ionises. All the negative charge is located on the oxygen atom, and isn't spread around at all. That means that you would expect the pKa of water to be similar to that of ethanol - and it is. The pKa of ethanol is 16; that of water is 15.7. There is a slight difference. Remember that the higher the value of pKa, the weaker the acid. So ethanol is a slightly weaker acid than water. | |
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Note: If you have done any work on Ka and Kw, you may be slightly worried about the 15.7 value of pKa for water. This comes from the different ways in which Ka and Kw are defined. There is a fairly simple explanation of this on this site. I am wary of links to other sites because they change. If this link doesn't work, please contact me via the address on the about this site page. | |
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If ethanol is a slightly weaker acid than water, why is that? In their syllabus support material, CIE offers an explanation of this in terms of the positive inductive effect of the alkyl group. A positive inductive effect is often described as an "electron pushing effect". So an ethyl group will push electrons away from itself onto the oxygen atom in the ethoxide ion. That makes the oxygen even more negative, and so even more likely to pick up a hydrogen ion again to return to the alcohol. | |
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Note: If you aren't happy about this inductive effect of alkyl groups then you could look at this page about carbocations (not exactly what we are talking about here, but similar enough to be useful), and perhaps also this page about electronegativity (read the bit about inductive effects about half-way down the page). Incidentally, I'm not too happy about this explanation, because, although it works for most alcohols, it doesn't work for methanol. Methanol has a pKa of 15.5, which makes it a slightly stronger acid than water. I have no idea why that is, but any decent explanation should be able to account for exceptions like this. For CIE purposes, for ethanol and water, you only need to learn the bit just above this box. | |
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In summary: phenol is a stronger acid than water which is a slightly stronger acid than ethanol.
© Jim Clark 2020 |
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