Animated Solution for Chemistry - Organic Chemistry: The monomer (X) involved in the synthesis of Nylon 6,6 gives positive carbylamine test. If 10 moles of X are analyzed using Dumas method, the amount (in grams) of nitrogen gas evolved is _______.
Use: Atomic mass of N (in amu) = 14
Enter Numerical Value:
Visualized Solution
Identifying Monomer X
Nylon-6,6 is synthesized from two monomers:
1. Hexamethylenediamine: H2N−(CH2)6−NH2
2. Adipic acid: HOOC−(CH2)4−COOH
Monomer X gives a positive carbylamine test, which is characteristic of primary amines (1∘ amines).
Therefore, X is Hexamethylenediamine.
Molecular Formula of X
Structure of X: H2N−(CH2)6−NH2
Counting the atoms:
Carbon (C) = 6
Hydrogen (H) = 2+12+2=16
Nitrogen (N) = 2
Molecular Formula: C6H16N2
The Dumas Method
The Dumas method is used for the quantitative estimation of nitrogen.
The organic compound is heated with Copper(II) oxide (CuO).
All nitrogen in the compound is converted to Nitrogen gas (N2).
Reaction: CxHyNzCuO,ΔxCO2+2yH2O+2zN2
Stoichiometry of N2 Evolution
For monomer X (C6H16N2), z=2.
Moles of N2 produced per mole of X = 2z=22=1 mole.
Therefore, 1 mole of X≡1 mole of N2.
Calculating Moles for the Given Sample
Given: 10 moles of monomer X are analyzed.
Since 1 mole X→1 mole N2
Moles of N2 evolved = 10 moles.
Final Mass Calculation
Molar mass of N2=2×14=28 g/mol.
Mass of N2 evolved = Moles×Molar Mass
Mass = 10 moles×28 g/mol
Mass = 280 g
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The Sigma Insight: Polymers
Solution Diagram
The journey to solving this problem is a beautiful blend of organic polymer chemistry and quantitative analysis. It tests your ability to identify a compound from its chemical properties and then apply stoichiometric principles to a classic analytical method. Let's break it down step by step.
Decoding the Monomer
The problem begins by introducing a monomer, labeled X, which is used in the synthesis of Nylon 6,6.
Nylon 6,6 is a well-known condensation polymer. It is synthesized from two specific monomers:
1. Hexamethylenediamine: H2N−(CH2)6−NH2
2. Adipic acid: HOOC−(CH2)4−COOH
We are given a crucial piece of evidence: monomer X gives a positive carbylamine test. The carbylamine test (also known as the isocyanide test) is a definitive chemical test used exclusively to detect the presence of primary amines (1∘ amines).
Looking at our two candidates, adipic acid is a dicarboxylic acid and will not respond to this test. Hexamethylenediamine, on the other hand, possesses two primary amine groups. Therefore, we can confidently conclude that monomer X is hexamethylenediamine.
The Molecular Formula
To proceed with any quantitative analysis, we need the exact molecular formula of hexamethylenediamine.
Let's count the atoms in H2N−(CH2)6−NH2:
- Carbon (C): There are 6 carbon atoms in the central chain.
- Hydrogen (H): There are 6×2=12 hydrogens in the chain, plus 2 on each nitrogen, giving a total of 12+2+2=16 hydrogen atoms.
- Nitrogen (N): There is one nitrogen atom at each end, totaling 2 nitrogen atoms.
This gives us the molecular formula: C6H16N2.
The Dumas Method
The problem then states that 10 moles of this monomer are analyzed using the Dumas method.
The Dumas method is a classic quantitative technique used to determine the nitrogen content in an organic compound. In this method, a known mass of the organic compound is strongly heated with copper(II) oxide (CuO) in an atmosphere of carbon dioxide.
During this vigorous oxidation, the carbon and hydrogen in the compound are converted into carbon dioxide and water, respectively. The most important part for us is that all the nitrogen present in the compound is liberated as free nitrogen gas (N2).
The general chemical equation for this process is:
Let's apply this to our monomer, C6H16N2. Here, the number of nitrogen atoms per molecule, z, is 2.
According to the stoichiometry of the Dumas method, 1 mole of the compound will produce 2z moles of N2 gas.
Moles of N2=22=1 mole
This means there is a simple 1:1 molar ratio between hexamethylenediamine and the nitrogen gas evolved.
The problem asks us to analyze 10 moles of monomer X.
Since 1 mole of X yields 1 mole of N2, it naturally follows that 10 moles of X will yield exactly 10 moles of N2 gas.
Finally, we need to find the mass of this evolved gas in grams. We know the atomic mass of nitrogen is 14 amu, so the molar mass of N2 gas is 2×14=28 g/mol.
Mass of N2=Moles×Molar Mass
Mass of N2=10 moles×28 g/mol=280 g
The total amount of nitrogen gas evolved is 280 grams.