Chemguide: Support for CIE A level Chemistry

Learning outcome 32: Hydroxy compounds

32.2: Phenol

Learning outcome 32.2.2

This multi-part statement deals with some properties of phenol. Read the individual statements in your syllabus as you go along.

Important background

First read the page introducing phenol.

Statements 32.2.2(a) and 32.2.2(b)

These deal with the reactions of phenol with bases and with metallic sodium. You will find this covered on the page about the acidity of phenol.

Acidity is also covered in statements 32.2.3 and 32.2.4, but you can't understand these reactions without knowing something about it now. So read all of this page.

The syllabus asks for the reactions with bases - it does not just ask for sodium hydroxide. So you must be aware that phenol won't react with bases such as carbonates or hydrogencarbonates.

In CIE exam questions, you are probably more likely to be asked for these reactions in more complicated molecules than in phenol itself. You can assume that these reactions will be the same even if other things are attached to the benzene ring as well as the -OH group.

Statement 32.2.2(c)

This is about the reaction of phenol with diazonium salts. Since you have probably never heard of such things at this point, I shall leave this until the reaction comes up again in statement 34.2.4(a).

Statement 32.2.2(d) and 32.2.2(e)

You will find everything you need on the page about ring reactions of phenol.

You can ignore the reaction between phenol and concentrated nitric acid. As you will see, the syllabus specifies dilute nitric acid at room temperature.

Again, be aware that you may well be asked about these reactions in more complicated molecules where there are other things attached to the ring. And again, you can assume that the reactions will still be the same - with the -OH group directing bromine atoms or nitro groups into the 2- (next door) and 4- (opposite) positions.

Obviously, if there is something else already present in one or more of those positions, then an incoming group can't go there.

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© Jim Clark 2020