Question

Identify the reaction products, and write an equation for the following reactions of \(\mathrm{CH}_{2}=\mathrm{CHCH}_{2} \mathrm{OH}.\) (a) \(\mathrm{H}_{2}\) (hydrogenation, in the presence of a catalyst (b) Oxidation (excess oxidizing agent) (c) Addition polymerization (d) Ester formation, using acetic acid

Short answer

(a) \\(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{CH}_{2}\mathrm{OH}\\) (b) \\(\mathrm{CH}_2\mathrm{COOH} + \mathrm{CO}_2 + \mathrm{H}_2\mathrm{O}\\) (c) Polymer chain (d) \\(\mathrm{CH}_{2}=\mathrm{CHCH}_{2}\mathrm{OOCCH}_{3}\\)

Step-by-step solution

Understanding Hydrogenation

In hydrogenation, \(\mathrm{CH}_{2}=\mathrm{CHCH}_{2}\mathrm{OH}\) reacts with \(\mathrm{H}_2\) in the presence of a catalyst like palladium or platinum. This process turns the double bond into a single bond. The product will be \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{CH}_{2}\mathrm{OH}.\)

Writing the Hydrogenation Equation

The balanced reaction for hydrogenation is: \\(\mathrm{CH}_{2}=\mathrm{CHCH}_{2}\mathrm{OH} + \mathrm{H}_2 \rightarrow \mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{CH}_{2}\mathrm{OH}.\)

Understanding Oxidation

In oxidation with an excess of an oxidizing agent, the alcohol \(\mathrm{OH}\) group is oxidized to a carboxylic acid. The double bond may also be cleaved, forming \(\mathrm{CH}_2\mathrm{COOH}+\mathrm{CO}_2+\mathrm{H}_2\mathrm{O}.\)

Writing the Oxidation Equation

The balanced reaction for oxidation is: \\(\mathrm{CH}_{2}=\mathrm{CHCH}_{2}\mathrm{OH} + 3[O] \rightarrow \mathrm{CH}_2\mathrm{COOH} + \mathrm{CO}_2 + \mathrm{H}_2\mathrm{O}.\)

Understanding Addition Polymerization

In addition polymerization, double bonds between carbon atoms are broken, and monomers link together. This converts \(\mathrm{CH}_{2}=\mathrm{CHCH}_{2}\mathrm{OH}\) into a larger polymer chain.

Writing the Addition Polymerization Equation

The polymerization can be represented as: \\(n(\mathrm{CH}_{2}=\mathrm{CHCH}_{2}\mathrm{OH}) \rightarrow [-\mathrm{CH}_{2}-\mathrm{CHCH}_{2}\mathrm{OH}-]_n.\)

Understanding Ester Formation

In ester formation, \(\mathrm{CH}_{2}=\mathrm{CHCH}_{2}\mathrm{OH}\) reacts with acetic acid (\(\mathrm{CH}_{3}\mathrm{COOH}\)). The alcohol and acid combine to form an ester and water.

Writing the Ester Formation Equation

The balanced reaction for esterification is: \\(\mathrm{CH}_{2}=\mathrm{CHCH}_{2}\mathrm{OH} + \mathrm{CH}_{3}\mathrm{COOH} \rightarrow \mathrm{CH}_{2}=\mathrm{CHCH}_{2}\mathrm{OOCCH}_{3} + \mathrm{H}_{2}\mathrm{O}.\)

Key concepts

Hydrogenation

Hydrogenation is a vital reaction in organic chemistry, where hydrogen gas (\( \mathrm{H}_2 \)) is added to unsaturated organic compounds. This process requires a catalyst, such as palladium or platinum. In the case of \( \mathrm{CH}_{2}=\mathrm{CHCH}_{2}\mathrm{OH} \), the double bond turns into a single bond, resulting in the product \( \mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{CH}_{2}\mathrm{OH} \).

• Converts double bonds to single bonds
• Requires a catalyst (e.g., palladium or platinum)
• Used to saturate organic molecules

Hydrogenation is widely used in the food industry to convert liquid oils into solid fats, besides its applications in creating fuel and various chemicals.

Oxidation

Oxidation involves the addition of oxygen or the removal of hydrogen from a molecule, fundamentally transforming its structure. It often involves an oxidizing agent, which accepts electrons from the substance being oxidized. In our example with \( \mathrm{CH}_{2}=\mathrm{CHCH}_{2}\mathrm{OH} \), the presence of an excess oxidizing agent (\([O]\)) alters not just the \( \mathrm{OH} \) group into a carboxylic acid but may also cleave the double bond, leading to products like \( \mathrm{CH}_2\mathrm{COOH} \), \( \mathrm{CO}_2 \), and \( \mathrm{H}_2\mathrm{O} \).

• Involves gain of oxygen/loss of hydrogen
• Uses oxidizing agents (e.g., \([O]\))
• Transforms alcohols into acids

Understanding oxidation reactions is crucial for fields like biochemistry and industrial chemistry, where they are responsible for processes ranging from energy production to material degradation.

Addition Polymerization

Addition polymerization is a chemical process where monomers with double bonds join together to form long polymer chains. This is a key method for creating various plastics and synthetic rubbers. For \( \mathrm{CH}_{2}=\mathrm{CHCH}_{2}\mathrm{OH} \), double bonds open up, allowing the monomers to link into polymers like \([-\mathrm{CH}_{2}-\mathrm{CHCH}_{2}\mathrm{OH}-]_n\).

• Involves breaking of double bonds
• Creates long polymer chains
• Used in production of plastics

This process is critical to the production of everyday materials, allowing for the customization of polymer properties to suit various commercial and industrial needs.

Ester Formation

Ester formation, or esterification, is a fascinating reaction where an alcohol and an acid react to form an ester and water. It's a typical reaction in organic chemistry, exemplified when \( \mathrm{CH}_{2}=\mathrm{CHCH}_{2}\mathrm{OH} \) combines with acetic acid (\( \mathrm{CH}_{3}\mathrm{COOH} \)). This reaction yields an ester, \( \mathrm{CH}_{2}=\mathrm{CHCH}_{2}\mathrm{OOCCH}_{3} \), and water (\( \mathrm{H}_2\mathrm{O} \)).

• Creates an ester from alcohol and acid
• Releases water as a byproduct
• Common in production of fragrances and flavorings

Esterification is essential in both natural and industrial contexts, contributing to the creation of many compounds utilized in the manufacture of perfumes, food additives, and pharmaceuticals.