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.
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13. Alkenes, Alkynes, and Aromatic Compounds
Intro to Addition Reactions
Problem 54
Textbook Question
If 2-methyl-2-pentene were converted into 1-hexene, what kind of reaction would that be?

1
Step 1: Recognize the structural change in the molecules. 2-methyl-2-pentene is a branched alkene, while 1-hexene is a straight-chain alkene. This indicates a rearrangement of the carbon skeleton.
Step 2: Understand the type of reaction involved. The conversion of a branched alkene to a straight-chain alkene typically involves an isomerization reaction, where the connectivity of atoms is rearranged without adding or removing atoms.
Step 3: Recall that isomerization reactions often occur under specific conditions, such as the presence of a catalyst (e.g., acid or metal catalyst) and heat, which facilitate the rearrangement of the double bond and carbon chain.
Step 4: Consider the mechanism. In this case, the double bond in 2-methyl-2-pentene shifts position, and the branching is removed to form the straight-chain structure of 1-hexene. This involves breaking and reforming bonds within the molecule.
Step 5: Conclude that the reaction is an isomerization reaction, specifically an alkene isomerization, which changes the structure of the molecule while maintaining the same molecular formula (C6H12).

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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Elimination Reaction
An elimination reaction involves the removal of atoms or groups from a molecule, resulting in the formation of a double bond. In the case of converting 2-methyl-2-pentene to 1-hexene, a double bond is formed by eliminating a small molecule, typically water or hydrogen halide, from the starting alkene.
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Hydrocarbon Structure
Understanding hydrocarbon structure is essential for analyzing reactions involving alkenes. 2-methyl-2-pentene is a branched alkene, while 1-hexene is a straight-chain alkene. The structural differences influence the type of reactions that can occur, including the mechanisms of elimination and rearrangement.
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Rearrangement Reaction
A rearrangement reaction involves the reorganization of the molecular structure to form a different isomer. In this case, converting 2-methyl-2-pentene to 1-hexene may involve a rearrangement step where the carbon skeleton is altered, leading to the formation of a new alkene with a different position of the double bond.
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