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Ch.13 Alkenes, Alkynes, and Aromatic Compounds
McMurry - Fundamentals of GOB 8th Edition
McMurry8th EditionFundamentals of GOBISBN: 9780134015187Not the one you use?Change textbook
Chapter 13, Problem 17

The structure of vinyl acetate is shown below (the partial structure H2C=CH-is known as a vinyl group). When polymerized it produces poly(vinyl acetate), a polymer used for the springy soles in running shoes. Draw the structure of the polymer obtained if three vinyl acetate units underwent polymerization.
Chemical structure of vinyl acetate, showing H2C=CH- and the label "Vinyl acetate" on the right.

Verified step by step guidance
1
Understand the problem: Vinyl acetate is a monomer that contains a vinyl group (H₂C=CH-) and an acetate group (-OCOCH₃). During polymerization, the double bond in the vinyl group breaks, allowing the monomers to link together in a repeating chain.
Identify the repeating unit: The repeating unit in the polymer is derived from the vinyl acetate monomer. When the double bond in the vinyl group breaks, the monomer forms two single bonds that connect to adjacent monomers.
Visualize the polymerization process: In this case, three vinyl acetate units are polymerized. The double bonds in the vinyl groups of all three monomers break, and the monomers link together in a head-to-tail fashion, forming a chain.
Draw the structure of the polymer: Start with the first vinyl acetate unit, showing the broken double bond and the new single bonds connecting to the next monomer. Repeat this process for the second and third monomers, ensuring the acetate groups (-OCOCH₃) remain attached to the appropriate carbon atoms.
Label the repeating unit: Once the structure of the polymer is drawn, identify the repeating unit within the chain. This repeating unit represents the fundamental structure of poly(vinyl acetate) and can be enclosed in brackets with a subscript 'n' to indicate the polymer's length.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Vinyl Group

The vinyl group is a functional group characterized by the presence of a carbon-carbon double bond, specifically represented as H₂C=CH-. It is a key building block in organic chemistry, particularly in the formation of polymers. In the context of vinyl acetate, the vinyl group allows for the polymerization process, where multiple vinyl acetate units can link together to form long chains.
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Polymerization

Polymerization is a chemical process in which small molecules, known as monomers, chemically bond to form a larger, more complex structure called a polymer. This process can occur through various mechanisms, including addition polymerization, where unsaturated monomers like vinyl acetate react to form long chains. Understanding polymerization is essential for predicting the structure and properties of the resulting polymer.
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Poly(vinyl acetate)

Poly(vinyl acetate) is a synthetic polymer derived from the polymerization of vinyl acetate monomers. It is known for its flexibility, adhesive properties, and is commonly used in various applications, including adhesives and coatings. The structure of poly(vinyl acetate) consists of repeating units of vinyl acetate, which influences its physical properties and usability in products like running shoe soles.
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