Question

Hydrogen bonding between polyamide chains plays an important role in determining the properties of a nylon such as nylon 6,6 (Table 12.5 ). Draw the structural formulas for two adjacent chains of nylon 6,6 and show where hydrogenbonding interactions could occur between them.

Short answer

The structural formulas for two adjacent chains of nylon 6,6 can be represented as follows: \[ {*} CO - (CH_2)_4 - CO - NH - (CH_2)_4 - NH {*} (CH_2)_6 - {*} CO \\ | \\ {*} CO - (CH_2)_4 - CO - NH - (CH_2)_4 - NH {*} (CH_2)_6 - {*} CO \] The dashed line between the nitrogen atom bonded to the hydrogen and the neighboring oxygen atom on each chain represents hydrogen bonding interactions, which contribute to the physical properties of the polymer.

Step-by-step solution

Draw the repeating unit of 1,6-diaminohexane and adipoyl chloride combination

Draw the structural formulas for both 1,6-diaminohexane and adipoyl chloride, and connect them by an amide bond resulting from the condensation polymerization. The resulting unit structure will be: \[ \overset{O}{\Rightsquigarrow}{C} {*} NH - (CH_2)_4 - NH {*} {CO} - (CH_2)_4 - (CO) \] 2.

Draw the first chain of the nylon 6,6 polymer

Draw a repeating chain by extending alligator lines (C * and N * symbolize the continuation of the chain) from both ends of the previous structure, showing that it is part of the polymer chain. \[ {*} CO - (CH_2)_4 - CO - NH - (CH_2)_4 - NH {*} (CH_2)_6 - {*} CO \] 3.

Draw the second chain of the nylon 6,6 polymer

Draw another similar polymer chain, parallel and adjacent to the first chain. Make sure the chains are oriented with the amide groups facing each other so that hydrogen bonding can occur between them. \[ {*} CO - (CH_2)_4 - CO - NH - (CH_2)_4 - NH {*} (CH_2)_6 - {*} CO \] 4.

Indicate the hydrogen bonding interactions

Draw dashed lines between the nitrogen atom bonded to the hydrogen and the neighboring oxygen atom with a lone pair of electrons on each chain to represent hydrogen bonds. This will show where hydrogen bonding interactions could occur between the two chains. \[ H {*} N - (CH_2)_4 - NH {*} (CH_2)_6 - {*} CO \\ | \\ {*} CO - (CH_2)_4 - CO - NH - (CH_2)_4 - NH {*} (CH_2)_6 - {*} CO \] The final drawing represents two adjacent nylon 6,6 chains indicating the hydrogen bonding interactions between the amide groups.

Key concepts

Hydrogen Bonding

Hydrogen bonding is a special type of dipole-dipole interaction that occurs when a hydrogen atom is bonded to an electronegative atom, such as nitrogen or oxygen. In the case of nylon 6,6, hydrogen bonds form between the hydrogen atoms attached to the nitrogen in the amide groups and the oxygen atoms from the carbonyl groups on adjacent polymer chains.
This interaction is crucial because it increases the strength and stability of the polymer by holding the chains together.

• Hydrogen bonds are generally weaker than covalent bonds but stronger than van der Waals interactions.
• They play a significant role in determining the physical properties of materials, such as melting point and tensile strength.
• In polymers like nylon 6,6, they significantly contribute to density and durability.

These bonds can form and break relatively easily, which allows the material to be flexible yet strong. Understanding these interactions helps in the design of materials with desired mechanical properties.

Polymer Chains

Polymer chains are the fundamental building blocks of all polymers, including nylon 6,6. A polymer is essentially a long, repeating chain of molecules made up of smaller units called monomers.
In nylon 6,6, the polymer chains consist of repeating units formed from 1,6-diaminohexane and adipoyl chloride.
The term 'nylon 6,6' refers to the six carbon atoms in each of the monomer precursors.

• The process that creates these chains is called polymerization, specifically condensation polymerization in the case of nylon 6,6.
• During this process, each monomer unit joins together, forming long chains while releasing small molecules, such as water.
• These chains can be very long, giving the material its mechanical strength and elasticity.

Understanding the structure of polymer chains helps chemists to predict the properties of the material, allowing for innovation in a variety of applications, from textiles to engineering plastics.

Amide Groups

Amide groups are pivotal in connecting polymer chains in materials like nylon 6,6. Each amide bond is formed when an amine group (\( ext{-NH}_2 \)) from one monomer reacts with a carboxyl group (\( ext{-COOH} \)) from another, resulting in the release of a molecule of water and formation of the amide linkage.

• Amide groups are characterized by the functional group \( ext{-CONH} \), where the nitrogen is bonded directly to a carbonyl group.
• These groups are highly polar, leading to the potential for strong interactions between adjacent chains via hydrogen bonding.
• The presence of amide groups provides the polymer with increased rigidity and resistance to chemical and thermal degradation.

The formation of amide groups is essential for the durability and effectiveness of the materials in which they are used. They are crucial for the resilience and sustainability of nylon 6,6 and other similar polyamides.