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Chapter 31: Problem 2

Draw the structures of the following amines: (a) 2 -hexylamine; (b) 3,3 -dimethyl-1-heptylamine; (c) triethylamine; (d) dimethylamine; (e) 1,4 -butanediamine; (f) isopropylamine; (g) \(N, N\) -dimethylbutylamine; (h) 1 -octylamine; (i) benzylamine. Classify each compound as a primary, secondary or tertiary amine.

Short Answer

Expert verified
Primary: (a), (b), (e), (f), (h), (i); Secondary: (d); Tertiary: (c), (g).

Step by step solution

01

Understand Amines

Amines are organic compounds derived from NH鈧� (ammonia) with one or more hydrogen atoms replaced by alkyl or aromatic groups. Classification depends on the number of organic substituents attached to the nitrogen atom.
02

Draw 2-Hexylamine

2-Hexylamine has the structure: CH鈧�-(CH鈧�)鈧�-CH-NH鈧�. The nitrogen atom is connected to the second carbon of the hexane chain, and this compound is a primary amine.
03

Draw 3,3-Dimethyl-1-Heptylamine

3,3-Dimethyl-1-heptylamine has the structure: CH鈧�-(CH鈧�)鈧�-C(CH鈧�)鈧�-CH鈧�-NH鈧�. The nitrogen atom is attached to the 1st carbon of the heptane chain with two methyl groups on the 3rd carbon, making it a primary amine.
04

Draw Triethylamine

Triethylamine has the structure: N(CH鈧侰H鈧�)鈧�. Here, the nitrogen atom is connected to three ethyl groups, classifying it as a tertiary amine.
05

Draw Dimethylamine

Dimethylamine has the structure: NH(CH鈧�)鈧�. The nitrogen atom is bonded to two methyl groups and one hydrogen atom, making this a secondary amine.
06

Draw 1,4-Butanediamine

1,4-Butanediamine, also known as putrescine, has the structure: NH鈧�-(CH鈧�)鈧�-NH鈧�. It contains two primary amine groups each located at an end of the butane chain, classifying it as a primary diamine.
07

Draw Isopropylamine

Isopropylamine has the structure: (CH鈧�)鈧侰H-NH鈧�. The nitrogen is bonded to an isopropyl group, which is considered a primary amine because it contains only one alkyl substituent.
08

Draw N,N-Dimethylbutylamine

N,N-Dimethylbutylamine has the structure: CH鈧�(CH鈧�)鈧�-N(CH鈧�)鈧�. The nitrogen atom is attached to a butyl group and two methyl groups, classifying it as a tertiary amine.
09

Draw 1-Octylamine

1-Octylamine has the structure: CH鈧�-(CH鈧�)鈧�-NH鈧�. The amine group is attached to the 1st carbon of an octane chain, making it a primary amine.
10

Draw Benzylamine

Benzylamine has the structure: C鈧咹鈧�-CH鈧�-NH鈧�. This has a benzyl group (a phenyl attached to a methylene group) bonded to the nitrogen, classifying it as a primary amine.

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Organic Chemistry
Organic chemistry is the branch of chemistry dedicated to the study of carbon-containing compounds. These compounds generally contain carbon atoms bonded to hydrogen, oxygen, nitrogen, and other elements. Amines are an important category within organic chemistry, primarily due to their role in building more complex molecules. Amine molecules are characterized by their nitrogen atoms, which can form bonds with hydrogen, carbon, and other elements, resulting in a diverse array of compounds. Understanding organic chemistry lays the foundation for exploring how different atomic arrangements impact the chemical properties and reactivity of amines.
Functional Groups
In organic chemistry, a functional group is a specific grouping of atoms within molecules that determine the characteristics of the compound. Amines are characterized by having a nitrogen atom bonded to one or more alkyl or aromatic groups. The functional group for amines is often depicted by the general structure \ \(R{_n}NH_{3-n}\), where \(R\) stands for the organic substituent and \(n\) indicates the degree of substitution. This configuration impacts the molecule's properties, such as solubility and basicity. Functional groups are essential because they allow chemists to predict the behavior and reactivity of molecules in chemical reactions.
Molecular Structure
The molecular structure of a compound affects not only its identity but also its function and reactivity. Amines are known for their trigonal pyramidal shape around the nitrogen atom, which arises because of the lone pair electrons. This geometry influences intermolecular interactions like hydrogen bonding, impacting boiling and melting points. In identification, line drawings or condensed formulas can be used to depict the 3D placement of atoms relative to each other. Understanding molecular structure is crucial for categorizing amines correctly into primary, secondary, or tertiary classes.
Primary Amines
Primary amines are a type of amine where the nitrogen atom is bonded to one substituent group, alongside two hydrogen atoms. Their general formula is \( RNH_2 \), where \( R \) represents the substituent. They are considered the simplest form of amines and generally exhibit strong hydrogen bonding due to the presence of two hydrogen atoms, which contributes to relatively high boiling points. Examples from the exercise include compounds like 2-hexylamine and benzylamine, each depicting how primary amines can vary greatly in molecular structure despite sharing the same functional group.
Secondary Amines
Secondary amines involve a nitrogen atom bonded to two organic substituents and one hydrogen atom. Their general representation is \( R_2NH \). The presence of hydrogen allows them to participate in hydrogen bonding, albeit less effectively than primary amines, due to having only one hydrogen attached to the nitrogen. Dimethylamine is an example from the exercise, highlighting its classification as a secondary amine as it is bonded to two methyl groups. The reduced direct hydrogen bonding in comparison to primary amines allows for varied physical properties, making them unique in organic synthesis.
Tertiary Amines
Tertiary amines are characterized by a nitrogen atom bonded to three organic substituents with no hydrogen atom attached. The structure can be captured by \( R_3N \). Since they lack a hydrogen atom attached to nitrogen, they cannot form hydrogen bonds, which often results in lower boiling points than primary or secondary amines. Triethylamine and N,N-dimethylbutylamine are examples outlined in the exercise that illustrate how tertiary amines can vary in molecular structure. Despite their inability to hydrogen bond, they are crucial in synthesis and chemical reactions, acting as bases and nucleophiles in various organic reactions.

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Most popular questions from this chapter

What problems would be encountered if you used the reaction of 1 -bromohexane with \(\mathrm{NH}_{3}\) as a route to 1-hexylamine?

Write down the equilibria to which the following \(\mathrm{p} K_{\mathrm{a}}\) and \(\mathrm{p} K_{\mathrm{b}}\) values refer: \((\mathrm{a}) \mathrm{p} K_{\mathrm{b}}\) for methylamine (b) \(\mathrm{p} K_{\mathrm{a}}\) values for the conjugate acids of \(1,3-\) propanediamine; (c) \(\mathrm{p} K_{\mathrm{a}}\) for triethylammonium ion; (d) \(\mathrm{p} K_{\mathrm{b}}\) for benzylamine; (e) \(\mathrm{p} K_{\mathrm{a}}\) for the conjugate acid of 1-butylamine.

The mass spectrum of a compound \(\mathbf{X}\) has a parent peak at \(m / z=69 .\) The \(^{13} \mathrm{C}\) NMR spectrum of X has signals at \(\delta 119.9,19.3,19.0\) and \(13.3 \mathrm{ppm}\) Treatment of \(\mathbf{X}\) with \(\mathrm{LiAlH}_{4}\) gives compound \(\mathbf{Y}\), the mass spectrum of which contains major peaks at \(m / z=73\) and \(31 .\) The \(^{13} \mathrm{C}\) NMR spectrum of \(\mathbf{Y}\) shows signals at \(\delta 42.0,36.1,20.1\) and \(13.9 \mathrm{ppm}\) Elemental analytical data for \(\mathbf{X}\) and \(\mathbf{Y}\) are: \(\mathbf{X}, 69.6 \%\) \(\mathrm{C}, 20.3 \% \mathrm{N}, 10.1 \% \mathrm{H} ; \mathrm{Y}, 65.7 \% \mathrm{C}, 19.2 \% \mathrm{N}, 15.1 \%\) H. Compound \(\mathbf{Z}\) is an isomer of \(\mathbf{X} ;\) its \(^{1}\) H NMR spectrum contains signals at \(\delta 1.3\) (doublet, \(6 \mathrm{H}\) ), 2.7 (septet, 1 H) ppm. Suggest identities for \(\mathbf{X}, \mathbf{Y}\) and \(\mathbf{Z}\) How would Y react with (a) \(\mathrm{H}_{2} \mathrm{SO}_{4},\) (b) an excess of MeI and (c) butanoyl chloride, \(\mathrm{C}_{3} \mathrm{H}_{7} \mathrm{COCl} ?\)

Give structural representations of the following salts: (a) tetraethylammonium chloride; (b) tetrabutylammonium bromide; (c) diethylammonium sulfate; (d) \(N, N\) -dimethylbenzylammonium bromide.

(a) Suggest how the reaction of \(\mathrm{NH}_{3}\) with 1-bromopropane might proceed. (b) Suggest a method of preparing 1-hexylamine in high yield from 1-bromohexane.
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