Chapter 11: Problem 31
\(\mathrm{C}_{3} \mathrm{H}_{9} \mathrm{~N}\) cannot represent (a) Quaternary salt (b) \(1^{\circ}\) amine (c) \(2^{\circ}\) amine (d) \(3^{\circ}\) amine
Short Answer
Expert verified
Quaternary salt is not possible.
Step by step solution
01
Analyze the Formula
The given formula is \(\mathrm{C}_{3}\mathrm{H}_{9}\mathrm{~N}\). This formula represents an organic compound that contains carbon, hydrogen, and nitrogen atoms.
02
Consider Quaternary Salt
A quaternary ammonium salt should have a nitrogen atom bonded to four other groups, most commonly alkyl groups, making it positively charged (e.g., \(\mathrm{R}_{4}\mathrm{N}^{+}\)). This requires at least \(\mathrm{C}_{4}\mathrm{H}_{9}\mathrm{~N}^{+}\), which cannot match \(\mathrm{C}_{3}\mathrm{H}_{9}\mathrm{~N}\).
03
Assess Primary Amine
A primary amine has the general formula \(\mathrm{RNH}_{2}\). For three carbons, a primary amine can be \(\mathrm{C}_{3}\mathrm{H}_{7}\mathrm{NH}_{2}\), matching the formula \(\mathrm{C}_{3}\mathrm{H}_{9}\mathrm{~N}\).
04
Evaluate Secondary Amine
A secondary amine has the general formula \(\mathrm{R}_{2}\mathrm{NH}\). For the given formula, a possible structure is \(\mathrm{R} = \mathrm{CH}_{3}\), giving \(\left(\mathrm{CH}_{3}\right)_{2}\mathrm{NH}\), also matching \(\mathrm{C}_{3}\mathrm{H}_{9}\mathrm{~N}\).
05
Consider Tertiary Amine
A tertiary amine has the general formula \(\mathrm{R}_{3}\mathrm{N}\). The formula \(\left(\mathrm{CH}_{3}\right)_{3}\mathrm{N}\) matches \(\mathrm{C}_{3}\mathrm{H}_{9}\mathrm{~N}\), hence it can represent a tertiary amine.
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Quaternary Ammonium Salt
Quaternary ammonium salts are intriguing compounds in organic chemistry, characterized by a nitrogen atom that is surrounded by four alkyl or aryl groups. This results in a positively charged nitrogen core, denoted usually as \( \text{NR}_4^+ \). Due to this positive charge, quaternary ammonium salts often appear in crystalline form and are quite soluble in water.
What makes these salts different from other amines is the absence of a lone pair on the nitrogen atom, which arises because all four of the nitrogen's valence electrons are engaged in forming covalent bonds with the surrounding groups. A simple example is tetramethylammonium chloride, where the nitrogen is bonded to four methyl groups (\( \text{CH}_3\)) and a chloride anion as a counter-ion.
In many applications, these compounds are used as disinfectants, antistatic agents, and fabric softeners due to their ability to disrupt microbial cell membranes. It's essential to note that in the context of the original exercise, the compound \( \text{C}_3\text{H}_9\text{N} \) cannot form a quaternary salt because it lacks a fourth carbon necessary to satisfy the quaternary nitrogen structure requirements.
What makes these salts different from other amines is the absence of a lone pair on the nitrogen atom, which arises because all four of the nitrogen's valence electrons are engaged in forming covalent bonds with the surrounding groups. A simple example is tetramethylammonium chloride, where the nitrogen is bonded to four methyl groups (\( \text{CH}_3\)) and a chloride anion as a counter-ion.
In many applications, these compounds are used as disinfectants, antistatic agents, and fabric softeners due to their ability to disrupt microbial cell membranes. It's essential to note that in the context of the original exercise, the compound \( \text{C}_3\text{H}_9\text{N} \) cannot form a quaternary salt because it lacks a fourth carbon necessary to satisfy the quaternary nitrogen structure requirements.
Primary Amine
In organic chemistry, a primary amine features a nitrogen atom bonded to one carbon-containing group (the alkyl or aryl group) and two hydrogen atoms, following the general formula \( \text{RNH}_2 \). The structure resembles ammonia, but one hydrogen is replaced by an organic substituent.
Primary amines are common and versatile, often serving as building blocks for more complex molecules. A straightforward example is ethylamine, with the molecular structure \( \text{CH}_3\text{CH}_2\text{NH}_2 \).
In assessing \( \text{C}_3\text{H}_9\text{N} \), the primary amine framework is satisfied when the molecule is configured as \( \text{C}_3\text{H}_7\text{NH}_2 \), fulfilling the general requirement for forming a primary amine. These compounds play a crucial role in the synthesis of dyes, pharmaceuticals, and even agrochemicals.
Primary amines are common and versatile, often serving as building blocks for more complex molecules. A straightforward example is ethylamine, with the molecular structure \( \text{CH}_3\text{CH}_2\text{NH}_2 \).
In assessing \( \text{C}_3\text{H}_9\text{N} \), the primary amine framework is satisfied when the molecule is configured as \( \text{C}_3\text{H}_7\text{NH}_2 \), fulfilling the general requirement for forming a primary amine. These compounds play a crucial role in the synthesis of dyes, pharmaceuticals, and even agrochemicals.
Secondary Amine
Secondary amines have a distinct chemical structure where the nitrogen is bonded to two carbon-containing groups and one hydrogen atom. The general formula for these compounds is \( \text{R}_2\text{NH} \), representing two organic substituents attached to the nitrogen.
This structure leads to numerous secondary amines such as dimethylamine (\( \left(\text{CH}_3\right)_2\text{NH} \)), which is found naturally in some plants and animals. Secondary amines exhibit intermediate properties between primary and tertiary amines, including their reactivity and solubility in water.
When applied to the formula \( \text{C}_3\text{H}_9\text{N} \), it can perfectly represent a secondary amine like dimethylamine, as mentioned above, showing that the formula can account for a secondary amine's presence.
This structure leads to numerous secondary amines such as dimethylamine (\( \left(\text{CH}_3\right)_2\text{NH} \)), which is found naturally in some plants and animals. Secondary amines exhibit intermediate properties between primary and tertiary amines, including their reactivity and solubility in water.
When applied to the formula \( \text{C}_3\text{H}_9\text{N} \), it can perfectly represent a secondary amine like dimethylamine, as mentioned above, showing that the formula can account for a secondary amine's presence.
Tertiary Amine
Tertiary amines are characterized by a nitrogen atom connected to three carbon-containing groups. The framework for these amines is \( \text{R}_3\text{N} \), showing no hydrogen atoms directly attached to the nitrogen.
A classic example is trimethylamine, where the nitrogen atom binds to three methyl groups (\( \text{CH}_3\)), resulting in a common formula of \( \left( \text{CH}_3 \right)_3\text{N} \). This configuration contributes to characteristic odors and plays a significant role in processes such as food biodegradation.
In the context of \( \text{C}_3\text{H}_9\text{N} \), the structure aligns perfectly with a tertiary amine such as trimethylamine, demonstrating that the molecular formula is also capable of representing a tertiary amine. This illustrates the flexibility and diversity of nitrogen-based compounds in organic chemistry.
A classic example is trimethylamine, where the nitrogen atom binds to three methyl groups (\( \text{CH}_3\)), resulting in a common formula of \( \left( \text{CH}_3 \right)_3\text{N} \). This configuration contributes to characteristic odors and plays a significant role in processes such as food biodegradation.
In the context of \( \text{C}_3\text{H}_9\text{N} \), the structure aligns perfectly with a tertiary amine such as trimethylamine, demonstrating that the molecular formula is also capable of representing a tertiary amine. This illustrates the flexibility and diversity of nitrogen-based compounds in organic chemistry.
