Question

The product obtained on reaction of ethyl acetate with amalgamated sodium metal followed by hydrolysis is

Short answer

The product obtained on reaction of ethyl acetate with amalgamated sodium metal followed by hydrolysis is Acetic Acid (CH3COOH) and Ethanol (CH3CH2OH).

Step-by-step solution

React ethyl acetate with amalgamated sodium metal

First, we will react ethyl acetate (CH3COOCH2CH3) with amalgamated sodium metal. Amalgamated sodium is usually sodium dispersed in mercury and is used to enhance the reactivity of sodium metal. The reaction between ethyl acetate and amalgamated sodium can be represented as follows: Ethyl Acetate + 2Amalgamated Sodium → Sodium Ethoxide + Sodium Acetate $C{H}_{3}COOC{H}_{2}C{H}_3+2Na/Hg\to C{H}_{3}COONa+C{H}_{3}C{H}_{2}ONa$

Hydrolysis of the products obtained in Step 1

Now that we have obtained sodium acetate and sodium ethoxide from the reaction in Step 1, we will proceed with hydrolysis, which means we will react these products with water to convert them back to their corresponding acids and alcohols. Sodium Acetate + Water → Acetic Acid + Sodium Ion $$C{H}_{3}COONa+H_{2}O\to C{H}_{3}COOH+N{a}^{+}$$ Sodium Ethoxide + Water → Ethanol + Sodium Ion $$C{H}_{3}C{H}_{2}ONa+H_{2}O\to C{H}_{3}C{H}_{2}OH+N{a}^{+}$$

Write the overall reaction for the entire process

Now that we have obtained the products of individual reactions, we can write the overall reaction. In this reaction, we consider the reactants of the initial reaction and the final products obtained after hydrolysis. Ethyl Acetate + 2 Amalgamated Sodium + 2 Water → Acetic Acid + Ethanol + 2 Sodium Ions $$C{H}_{3}COOC{H}_{2}C{H}_3+2Na/Hg+2H_{2}O\to C{H}_{3}COOH+C{H}_{3}C{H}_{2}OH+2N{a}^{+}$$ So, the product obtained on reaction of ethyl acetate with amalgamated sodium metal followed by hydrolysis is Acetic Acid (CH3COOH) and Ethanol (CH3CH2OH).

Key concepts

Understanding Ethyl Acetate Reactions

Ethyl acetate, represented by the chemical formula CH₃COOCH₂CH₃, is commonly used in organic chemistry as a solvent and as a reactant in various chemical reactions. This colorless liquid possesses a pleasant, sweet smell, similar to that of pear drops. When ethyl acetate reacts with reagents like sodium metal, particularly amalgamated sodium, it undergoes a transformation.

Amalgamated sodium is a powerful reducing agent, commonly used to increase the reactivity of sodium by dispersing it in mercury. The presence of mercury allows for a more controlled release of sodium atoms, which can effectively donate electrons in a reaction. This is a crucial aspect as it drives the reaction forward, leading to a more efficient process.

During the reaction between ethyl acetate and amalgamated sodium, the ester is broken down into sodium salts of the constituent acid and alcohol. Specifically, sodium acetate (CH₃COONa) and sodium ethoxide (CH₃CH₂ONa) are formed. These products are pivotal for various subsequent chemical processes, including hydrolysis.

Amalgamated Sodium in Organic Synthesis

In organic synthesis, sodium in its amalgamated form is often used as it is more reactively manageable compared to pure sodium metal. The amalgam involves a mixture of sodium with mercury, which helps to tame the highly reactive and sometimes explosive nature of sodium.

Amalgamated sodium acts as a 'gentle' reductant, often employed in reactions that are sensitive to excessive reactivity, such as reductions of certain organic compounds. Using amalgamated sodium can help to avoid undesirable side reactions that might occur with other harsher reducing agents or with pure sodium metal itself.

To enhance understanding, consider amalgamated sodium as a 'controlled release' form of sodium, it can provide electrons steadily to the reaction, allowing a mild and more selective path to the desired products. In the context of ester reactions, like ethyl acetate, this controlled reduction is essential for breaking down the ester into sodium salts without damaging the functional groups.

Hydrolysis of Esters Explained

Esters are organic compounds that can be hydrolyzed, which means they can be broken down by water - a process aptly named hydrolysis. Hydrolysis reactions are a cornerstone in organic chemistry, essential for understanding the behavior of many biological and synthetic compounds.

When esters undergo hydrolysis, they are essentially reverted to their parent acid and alcohol. The sodium salts produced from the reaction with amalgamated sodium, sodium acetate, and sodium ethoxide, are perfect candidates for hydrolysis. The addition of water to these salts leads to the formation of acetic acid (CH₃COOH) and ethanol (CH₃CH₂OH), respectively.

The process of hydrolysis is not only fundamental in laboratory synthesis but also occurs naturally in living organisms. Many biological processes rely on the hydrolysis of esters; for example, the digestion of fats in our body involves the hydrolysis of esters by enzymes to release fatty acids and glycerol. Understanding the principles of hydrolysis is, therefore, beneficial not just for mastering organic synthesis, but also for comprehending biological functions.