What is the correct IUPAC name of the following compound? A. 2-amino-3-carboxyphenol B. 2-carboxy-6-hydroxyphenylamine C. 2-amino-3-hydroxybenzoic acid D. 2-carboxy-6-hydroxyaniline E. 2-nitro-3-phenolcarboxylic acid

Question

BlackTom AI · Accepted Answer

Carboxylic acid has the highest functional-group priority here, so the parent ring must be named as benzoic acid (benzoic acid = benzene-1-carboxylic acid).

1) Key concepts:
- IUPAC selects the principal functional group with highest seniority as the parent; carboxylic acid > alcohol > amine.
- Number the ring so the carboxyl carbon is C-1 and give substituents the lowest possible locants.
- Use prefixes amino- and hydroxy- for –NH2 and –OH substituents on a benzoic acid parent.

2) Step-by-step reasoning and numbering:
- Place the carboxyl group as position 1 (benzene-1-carboxylic acid = benzoic acid).
- Identify the other substituents on the ring relative to C-1. The structure shown has an amino group adjacent to the carboxyl (ortho) and a hydroxy group next to that (i.e., at the next carbon). That corresponds to substituents at C-2 (–NH2) and C-3 (–OH).
- Therefore the substituent locants are 2-amino and 3-hydroxy on benzoic acid.

3) Intermediate locant assignment:
- Parent: benzoic acid (1-CO2H)
- Substituents: 2-NH2, 3-OH
- Combined: 2-amino-3-hydroxybenzoic acid

4) Why this is correct:
- This name correctly uses the carboxylic acid as the parent and assigns the lowest locants to substituents. The substituent prefixes are standard (amino-, hydroxy-). The order of prefixes in the full name is alphabetical (amino before hydroxy) but locants are given explicitly: 2-amino-3-hydroxybenzoic acid.

5) Why the other options are incorrect:
- A (2-amino-3-carboxyphenol): treats phenol as parent and calls the CO2H a "carboxy" substituent — wrong because CO2H is higher priority and should be the parent.
- B (2-carboxy-6-hydroxyphenylamine) and D (2-carboxy-6-hydroxyaniline): treat aniline/phenylamine as parent with carboxyl as substituent and give different numbering — incorrect priority and incorrect locants.
- E (2-nitro-3-phenolcarboxylic acid): introduces a nitro group and a malformed substituent name ("phenolcarboxylic acid"); does not match the actual substituents.

6) Conclusion:
The correct IUPAC name is 2-amino-3-hydroxybenzoic acid, which matches answer C.

What is the correct IUPAC name of the following compound? A. 2-amino-3-carboxyphenol B. 2-carboxy-6-hydroxyphenylamine C. 2-amino-3-hydroxybenzoic acid D. 2-carboxy-6-hydroxyaniline E. 2-nitro-3-phenolcarboxylic acid单项选择题

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