IUPAC nomenclature retains the common name aniline for \(\mathrm{C}_{\mathrm{e}} \mathrm{H}_{3} \mathrm{NH}_{2}\), the simplest arcanatic amine. Its simple derinatives are named using the prefixes \(o, w\), and \(p\), or numbers to locate substituents. Several derivatives of aniline have common names that are still widely used. Among these are tolusdine for a methyd-suhatitusted aniline and anisidine for a methoxyl-substituted aniline.

Short Answer

Expert verified
Question: Provide the IUPAC name for the following derivative of aniline: The methoxy group is attached to the carbon atom two positions away from the NH2 group on the benzene ring. Answer: 3-Methoxyaniline

Step by step solution

01

Identifying the parent compound and substituents

First, identify the parent compound and the substituents attached to the parent compound. In this case, aniline (C6H5NH2) is the parent compound, and we have two derivatives: one with a methyl substituent (toluidine) and one with a methoxy substituent (anisidine).
02

Naming the substituent

Next, name the substituent based on its atom or group, and use appropriate prefixes or numbers to indicate the position of the substituent. For example: - In toluidine (methyl-substituted aniline), the substituent is a methyl group. - In anisidine (methoxy-substituted aniline), the substituent is a methoxy group.
03

Using ortho, meta, and para prefixes or numbers to indicate the substituent position

For derivatives of aniline, use the prefixes ortho (o-), meta (m-), and para (p-) or numbers (2-, 3-, 4-) to indicate the substituent location relative to the NH2 group (amino group) on the benzene ring. The position numbers start from the carbon atom connected to the NH2 group: - ortho (o-) or 2-: the substituent is located at the carbon atom adjacent to the amino group. - meta (m-) or 3-: the substituent is located at the carbon atom two positions away from the amino group. - para (p-) or 4-: the substituent is located at the carbon atom opposite to the amino group.
04

Combining the substituent name and location with the parent compound

Combine the substituent name and its location (using prefixes or numbers) with the parent compound (aniline) to get the IUPAC name of the derivative. Here are some examples: 1. o-Toluidine (ortho-Toluidine) or 2-Toluidine: CH3 is at the ortho position (carbon 2) to the NH2 group on the benzene ring of aniline. IUPAC name: 2-Methylaniline 2. m-Toluidine (meta-Toluidine) or 3-Toluidine: CH3 is at the meta position (carbon 3) to the NH2 group on the benzene ring of aniline. IUPAC name: 3-Methylaniline 3. p-Toluidine (para-Toluidine) or 4-Toluidine: CH3 is at the para position (carbon 4) to the NH2 group on the benzene ring of aniline. IUPAC name: 4-Methylaniline 4. o-Anisidine (ortho-Anisidine) or 2-Anisidine: OCH3 is at the ortho position (carbon 2) to the NH2 group on the benzene ring of aniline. IUPAC name: 2-Methoxyaniline 5. m-Anisidine (meta-Anisidine) or 3-Anisidine: OCH3 is at the meta position (carbon 3) to the NH2 group on the benzene ring of aniline. IUPAC name: 3-Methoxyaniline 6. p-Anisidine (para-Anisidine) or 4-Anisidine: OCH3 is at the para position (carbon 4) to the NH2 group on the benzene ring of aniline. IUPAC name: 4-Methoxyaniline

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Most popular questions from this chapter

Like ammonia, all amines are weak bases, and aqueous solutions of amines are basic. The following acid-base reaction between an amine and water is written uxing curved arross to emphasize that, in these proton-transfer reactions, the unshared pair of electrons on nitrogen forms a new covalent bond with hydrogen and displaces hydroxide ion.

All aliphatic amines have about the same hase strength, \(\mathrm{p} K_{\mathrm{2}}\) of the conjugate acid \(10.0-11.0\), and are slightly stronger bases than ammonia. The increase in basicity compared with ammonia can be attributed to the greater stability of an alkylammonium ion, as for example \(\mathrm{RCH}_{2} \mathrm{NH}_{3}{ }^{+}\)compared with the ammonium ion, \(\mathrm{NH}_{4}{ }^{+}\). This greater stability arises from the electron- releasing effect of alky groups and the resulting partial delocalization of the positive charge from nitrogen onto carbon in the alkylammonium ion.

The hasicitydecreasing effect of nitro substitution in the s-position is almost entirely the result of its inductive effect, whereas that of nitro substitution in the 4.position is attributable to both inductive and resonance effects. In the case of para suhstitution (as well as ortho substitution), delocalization of the lone pair on the amino nitrogen involves not only the carbons of the aromatic ring but alwo oxy gen atoms of the nitro group.

Amines are further divided into aliphatic and aromatic amines. In an aliphatic amine, all carbons bonded to nitrogen are derived from alkyl groups; in an aromatic amine, one or more of the groups bonded to nitrogen are aryl groups.

Common names for most aliphatic amines are derived by listing the alkyl groups bonded to nitrogen in alphabetical order in one word ending in the suffix awine, that ix, they are named as alkylamines.

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