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The following question was given in NCERT Exemplar Problems (Class XII): enter image description here

According to Wikipedia:

In organic chemistry, the aromatic alcohols or aryl-alcohols are a class of chemical compounds containing a hydroxyl group (—OH) bonded directly to an aromatic hydrocarbon group, in contrast to the benzyl alcohol, where the hydroxyl group is bonded indirectly to an aromatic carbon atom.

But, I didn't understood the part: aromatic alcohols or aryl-alcohols (as aromatic alcohols are not always aryl alcohols).

Further, we know that aryl halides are compounds in which halogen group (-X) is directly attached to an aromatic ring. In the same way, aryl alcohols also mean that those compounds in which hydroxyl group (-OH) is directly attached to an aromatic ring.

Hence, according to my understanding, the answer should be (ii), but the answer given is (iii).

Where I am wrong? And, what is an aromatic alcohol?

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  • $\begingroup$ Sometimes phenols (OH group connected to the aromatic ring) are not considered to be alcohols, basically because they are much more acidic than aliphatic alcohols. When you use such a convention, aromatic alcohols are those in which you have an aromatic ring and a hydroxyl group connected to a sp3 carbon. If NCERT follow this convention, the right answer would be III. $\endgroup$ Jun 13 '18 at 18:45
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    $\begingroup$ @MaxW aromatic alcohol is still used, but it means a compound which has both the alcohol group and an aromatic ring in its structure. $\endgroup$ Jun 13 '18 at 19:58
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    $\begingroup$ @Rahul It should be pointed out that Wikipedia is not to be considered an authoritative source and has many incongruities and errors of fact. $\endgroup$
    – Dr. J.
    Jun 14 '18 at 10:36
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    $\begingroup$ Answer (iii) is the correct one. $\endgroup$
    – porphyrin
    Jun 14 '18 at 15:03
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    $\begingroup$ I agree that the correct answer should be (ii). My only experience with NCERT questions are from Stack Exchange, but it seems that there are either many errors in those questions or they rely on unusual conventions. $\endgroup$
    – jerepierre
    Jun 14 '18 at 15:50
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'Aromatic alcohol' is not a term that appears anywhere in the IUPAC literature - while its meaning is evident, it doesn't make sense in the same way that 'aromatic heterocyclic' does so is probably best avoided. What is defined by IUPAC is the definition of a phenol, and the definition of an aryl group. The definitions below come from an old IUPAC glossary of 'class names' which, although old, is still referenced in the most recent organic nomenclature guidelines and the most recent IUPAC Gold Book.

phenols: Compounds having one or more hydroxy groups attached to a benzene or other arene ring

aryl groups: Groups derived from arenes by removal of a hydrogen atom from a ring carbon atom.

Glossary of Class Names of Organic Compounds and Reactive Intermediates Based on Structure. Pure App. Chem. 1995, 67, 1307

To actually answer your question, the answer is (II) - as Jerepierre alluded to, the NCERT books / guides are renowned for being less that accurate, and a quick search around chem.SE will reveal just how many errors there are! In this case, its hard to tell if the error is just due to typesetting (someone typed III instead of II), or it it lies with the ambiguity of the term 'aromatic alcohol' (is it referring to phenols, or is it referring to a compound which contains both an aryl ring and a hydroxyl group).

I think its fair to assume that the question is asking you to identify the phenols, in which case the answer is (II) is because A and D are the only structures in which the hydroxyl group is directly attached to a benzene or other arene ring, which is our working definition of a phenol / aromatic alcohol.

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    $\begingroup$ So, according to you, aromatic alcohol is not defined anywhere in the world of chemistry. Right? $\endgroup$ Jun 16 '18 at 15:20
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    $\begingroup$ No. Just according to me its an ambiguous term and not one used by IUPAC (the people who define the Internationally accepted system of nomenclature). $\endgroup$
    – NotEvans.
    Jun 16 '18 at 15:31
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    $\begingroup$ Unfortunately textbook was correct and Wikipedia article had a mistake at that moment. Aromatic alcohol is an alcohol that is aromatic and is not phenol. How otherwise would you call such compound? $\endgroup$
    – Mithoron
    Aug 12 '20 at 0:56
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    $\begingroup$ I've been working as a researcher in the chemical sciences for 20 years. I upvoted this answer and would assume without any other context that aromatic alcohols referred to things like phenols, napthols, furanols, pyridinols, pyrazinols, etc etc etc. I'm sure people do it sometimes but I can't recall people saying "aromatic alcohol" to mean benzylic alcohol or similar compounds. $\endgroup$
    – Curt F.
    Dec 16 '20 at 20:00

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