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) Propanol; (b) Acrylic acid; (c) Poly(propylene glycol); (d) Allyl acetate.

Step-by-step solution

Analyze the Reaction with Hydrogenation

When an alkene like \(\mathrm{CH}_2=\mathrm{CHCH}_2 \mathrm{OH}\) is subjected to hydrogenation in the presence of a catalyst such as Pd or Pt, the double bond is reduced, converting it into an alkane. The product of this reaction is propanol, \(\mathrm{CH}_3\mathrm{CH}_2\mathrm{CH}_2\mathrm{OH}\). The balanced equation for this reaction is:\[\mathrm{CH}_2=\mathrm{CHCH}_2\mathrm{OH} + \mathrm{H}_2 \xrightarrow{\text{Catalyst}} \mathrm{CH}_3\mathrm{CH}_2\mathrm{CH}_2\mathrm{OH}\]

Determine Products of Oxidation

When \(\mathrm{CH}_2=\mathrm{CHCH}_2 \mathrm{OH}\) is oxidized with an excess oxidizing agent, the alcohol group is first oxidized to form an aldehyde which further oxidizes to a carboxylic acid. The resulting product is acrylic acid, \(\mathrm{CH}_2=\mathrm{CHCOOH}\). The balanced equation for this oxidation process is:\[\mathrm{CH}_2=\mathrm{CHCH}_2 \mathrm{OH} \rightarrow \mathrm{CH}_2=\mathrm{CHCOOH}\]

Addition Polymerization Process

Addition polymerization of \(\mathrm{CH}_2=\mathrm{CHCH}_2 \mathrm{OH}\) involves the reaction of many monomer units, opening up their double bonds to form large polymer chains. The polymer formed will be poly(propylene glycol) with repeating units of \([-\mathrm{CH}_2-\mathrm{CHCH}_2 \mathrm{OH}-]_n\). The simplified reaction is:\[ n(\mathrm{CH}_2=\mathrm{CHCH}_2 \mathrm{OH}) \rightarrow [-\mathrm{CH}_2-\mathrm{CHCH}_2 \mathrm{OH}-]_n \]

Formulation of an Ester with Acetic Acid

The reaction of \(\mathrm{CH}_2=\mathrm{CHCH}_2 \mathrm{OH}\) with acetic acid to form an ester is called esterification. In this reaction, the alcohol group reacts with the carboxylic acid to form an ester and water, resulting in allyl acetate, \(\mathrm{CH}_2=\mathrm{CHCH}_2 \, \mathrm{OCOCH}_3\). The equation for the esterification reaction is:\[\mathrm{CH}_2=\mathrm{CHCH}_2 \mathrm{OH} + \mathrm{CH}_3 \mathrm{COOH} \rightarrow \mathrm{CH}_2=\mathrm{CHCH}_2 \mathrm{OCOCH}_3 + \mathrm{H}_2\mathrm{O}\]

Key concepts

Understanding Hydrogenation

Hydrogenation is a simple but crucial process in organic chemistry, where unsaturated compounds, such as alkenes and alkynes, are converted into saturated ones by adding hydrogen.
It typically involves the use of a metal catalyst like palladium (Pd) or platinum (Pt). In the case of the molecule \(\text{CH}_2=\text{CHCH}_2\text{OH}\), hydrogenation helps reduce the double bond in the alkene to a single bond, turning it into an alkane: propanol \(\text{CH}_3\text{CH}_2\text{CH}_2\text{OH}\).
This reaction \

Exploring Oxidation

Oxidation refers to the process where a molecule loses electrons, often resulting in the addition of oxygen or the removal of hydrogen.
In organic chemistry, oxidation of alcohols can convert them first to aldehydes and then to carboxylic acids, assuming there's enough oxidizing agent present.
For our molecule, \(\text{CH}_2=\text{CHCH}_2\text{OH}\), the hydroxyl group \(\text{-OH}\) is oxidized to form acrylic acid \(\text{CH}_2=\text{CHCOOH}\).
Notice the transformation involves multiple steps and includes intermediate aldehyde formation. \

Unraveling Addition Polymerization

Addition polymerization is fascinating as it involves the assembling of monomer molecules into larger structures, called polymers, by breaking their double bonds.
In this process, no atoms are lost, making it a kind of rearrangement of atoms. With \(\text{CH}_2=\text{CHCH}_2\text{OH}\), numerous monomers join to generate poly(propylene glycol).
This polymerization leads to chains with repeating units \([-\text{CH}_2-\text{CHCH}_2 \text{OH}-]_n\), where \(n\) denotes the number of repeating units forming.\

Esterification Process Explained

Esterification is a key reaction that forms esters, often recognized for their pleasant aromas.
It involves the reaction between an alcohol and a carboxylic acid, producing an ester and water.
In our example, when \(\text{CH}_2=\text{CHCH}_2\text{OH}\) reacts with acetic acid \(\text{CH}_3\text{COOH}\), it forms allyl acetate \(\text{CH}_2=\text{CHCH}_2 \text{OCOCH}_3\) and water.
One can remember that water is a byproduct of this reversible reaction. \