Ch. 19 - Amines

Wade9th EditionOrganic ChemistryISBN: 9780135213728Not the one you use?Change textbook

Wade 9th Edition

Ch. 19 - Amines

Problem 3a,b,c

Chapter 19, Problem 3a,b,c

Give correct names for the following amines:
(a)
(b)
(c)

Verified step by step guidance

Step 1: Identify the parent chain in each amine structure. The parent chain is the longest continuous carbon chain that contains the amine group (-NH2).

Step 2: Number the parent chain starting from the end closest to the amine group to give the amine the lowest possible locant (position number).

Step 3: Name the parent chain as an alkane, replacing the '-e' at the end of the alkane name with '-amine' to indicate the presence of the amine group. For example, methane becomes methanamine.

Step 4: If there are substituents (e.g., alkyl groups or other functional groups) attached to the parent chain, name and number them as prefixes, arranging them alphabetically in the final name.

Step 5: For secondary or tertiary amines (amines with two or three alkyl groups attached to the nitrogen), use the 'N-' prefix to indicate substituents directly attached to the nitrogen atom. For example, N-methylpropanamine indicates a methyl group attached to the nitrogen of a propanamine.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Amines

Amines are organic compounds derived from ammonia (NH3) by replacing one or more hydrogen atoms with alkyl or aryl groups. They can be classified as primary, secondary, or tertiary based on the number of carbon-containing groups attached to the nitrogen atom. Understanding the structure of amines is crucial for naming them correctly.

IUPAC Nomenclature

The International Union of Pure and Applied Chemistry (IUPAC) provides a systematic method for naming chemical compounds. For amines, the naming convention involves identifying the longest carbon chain attached to the nitrogen and using suffixes and prefixes to denote the presence of the amine functional group. Familiarity with these rules is essential for accurately naming amines.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In the case of amines, the amino group (-NH2) is the functional group that defines their reactivity and properties. Recognizing functional groups is vital for understanding how to name and classify organic compounds.

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Related Practice

Textbook Question

Rank each set of compounds in order of increasing basicity.

(b) aniline, p-methylaniline, p-nitroaniline

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Textbook Question

Determine which of the heterocyclic amines just shown are aromatic. Give the reasons for your conclusions.

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Textbook Question

Which of the amines listed next is resolved into enantiomers? In each case, explain why interconversion of the enantiomers does or does not take place.

(a) cis-2-methylcyclohexanamine

(b) N-ethyl-N-methylcyclohexanamine

(d) ethylmethylanilinium iodide

(e) methylethylpropylisopropylammoniumiodide

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Textbook Question

Draw the structures of the following compounds:

(a) tert-butylamine

(b) α-aminopropionaldehyde

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Textbook Question

Draw the structures of the following compounds: