Chapter 22: Problem 88
Draw the structure for each amine. \begin{equation}\begin{array}{l}{\text { a. isopropylamine }} \\ {\text { b. triethylamine }} \\ {\text { c. butylethylamine }}\end{array}\end{equation}
Short Answer
Expert verified
Isopropylamine has a nitrogen connected to two methyl groups and one hydrogen. Triethylamine has a nitrogen connected to three ethyl groups. Butylethylamine has a nitrogen connected to one butyl group and one ethyl group.
Step by step solution
01
Draw Isopropylamine
Begin with the primary amine (aminomethane) structure which has one carbon (C) attached to a nitrogen (N) with three hydrogens (H). Isopropylamine is a secondary amine, so replace two hydrogen atoms on the nitrogen with a propane chain, where the central carbon is connected to the nitrogen and has two methyl groups (CH3) attached to it.
02
Draw Triethylamine
Start with the basic amine structure, but this time it is a tertiary amine. So, the central nitrogen atom will be attached to three ethyl groups (CH2CH3). Replace three hydrogen atoms on the nitrogen with three ethyl groups to form triethylamine.
03
Draw Butylethylamine
Since butylethylamine is a secondary amine, you'll need one butyl group (CH2CH2CH2CH3) and one ethyl group (CH2CH3) attached to the nitrogen (N), replacing two of the three hydrogen atoms. Sketch the butyl group on one side and the ethyl group on the other side connected to the nitrogen.
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Isopropylamine
Isopropylamine is an organic compound that can be represented by the structural formula (CH3)2CHNH2. It belongs to the secondary amines group because the nitrogen atom is bonded to two carbon atoms that are part of the same isopropyl group, and one hydrogen atom.
To understand the structure, consider the following steps:
This yields isopropylamine, an amine with a simple branched structure, used in various chemical applications.
To understand the structure, consider the following steps:
- Identify the isopropyl group: a central carbon atom with two methyl groups (CH3) attached.
- Locate the nitrogen atom and attach it to the central carbon of the isopropyl group.
- Add one hydrogen atom to the nitrogen to complete the structure.
This yields isopropylamine, an amine with a simple branched structure, used in various chemical applications.
Triethylamine
Triethylamine, often abbreviated as TEA, is a ubiquitous tertiary amine with the chemical formula N(CH2CH3)3. As a tertiary amine, all three hydrogen atoms normally bonded to nitrogen in ammonia (NH3) are replaced by ethyl groups.
Here are the crucial points for its structure:
Here are the crucial points for its structure:
- Begin with a central nitrogen atom.
- Attach three ethyl groups (CH2CH3) to the nitrogen.
- Ensure there are no hydrogen atoms attached to the nitrogen, characteristic of tertiary amines.
Butylethylamine
Butylethylamine is an organic compound that falls into the category of secondary amines. Its molecular formula is C6H15N, indicating a nitrogen atom bonded to a butyl group (CH2CH2CH2CH3) and an ethyl group (CH2CH3).
The structure drawing involves these steps:
The structure drawing involves these steps:
- Start with a central nitrogen atom.
- Attach one butyl group to the nitrogen.
- Attach one ethyl group to the same nitrogen atom.
- Add one hydrogen atom to the nitrogen to complete the secondary amine structure.
Amine Functional Group
The amine functional group is a key feature in organic chemistry, represented as nitrogen attached to alkyl or aryl substituents and hydrogen atoms. Depending on the number of carbon-containing groups attached to nitrogen, amines are classified as primary, secondary, or tertiary.
The general characteristics include:
The general characteristics include:
- A lone pair of electrons on nitrogen, making amines basic and reactive.
- The ability to participate in hydrogen bonding due to the presence of a nitrogen-hydrogen bond (except in tertiary amines).
- A distinct odorous property that ranges from fishy to unpleasant smells.
Secondary Amine
Secondary amines are a category of amines where the nitrogen atom is bonded to two alkyl or aryl groups and one hydrogen atom. This can be visualized as NH with two R groups attached, where R represents a carbon-containing side chain.
Key points about secondary amines include:
Key points about secondary amines include:
- They often have a lower boiling point than their corresponding primary amines due to weaker hydrogen bonding.
- They can act as bases and nucleophiles in organic reactions.
- Secondary amines are often found in biologically active molecules such as pharmaceuticals.
Tertiary Amine
Tertiary amines feature a nitrogen atom connected to three alkyl or aryl groups with no hydrogen atoms directly attached to the nitrogen. The general formula for tertiary amines is N(R1)(R2)(R3), indicating three carbon groups taking the place of hydrogen atoms.
Important aspects of tertiary amines are:
Important aspects of tertiary amines are:
- They are unable to engage in hydrogen bonding with themselves because they lack a hydrogen atom bonded to nitrogen.
- They often have higher steric hindrance which affects their reactivity compared to primary and secondary amines.
- Tertiary amines are used as catalysts and can be found in many products such as drugs and dyes.