The main difference between acidic and basic hydrolysis is that acidic hydrolysis involves the use of an acid to break down a chemical bond, whereas basic hydrolysis involves the use of a base to break down a chemical bond.
Hydrolysis is a process in which a molecule is broken down into smaller components through a reaction with water. In hydrolysis, the water molecule contributes a hydroxyl group to one part of the molecule while it donates the remaining hydrogen ion to the other part of the molecule during hydrolysis. There are several types of hydrolysis, such as acidic hydrolysis, basic hydrolysis, enzymatic hydrolysis, and photolytic hydrolysis.
Key Areas Covered
1. What is Acidic Hydrolysis
– Definition, Features, Uses
2. What is Basic Hydrolysis
– Definition, Features, Uses
3. Difference Between Acidic and Basic Hydrolysis
– Comparison of Key Differences
Key Terms
Acidic Hydrolysis, Basic Hydrolysis
What is Acidic Hydrolysis
Acidic hydrolysis involves the use of an acid to break down a chemical compound. The acid catalyzes the cleavage of the chemical bond through a nucleophilic substitution reaction with the addition of water. This type of hydrolysis is useful in organic chemistry to break down esters, amides, and other functional groups. Here, a proton is donated to the molecule, which is hydrolyzed. This protonation weakens the bond holding the molecule together. Hence, the bond becomes more susceptible to break. For example, in the hydrolysis of an ester, acid donates a proton to the carbonyl group of the ester, which then results in the formation of a tetrahedral intermediate. This tetrahedral intermediate then breaks and forms a carboxylic acid and an alcohol.
The most common acid used in acidic hydrolysis is sulfuric acid. It is a strong acid that can donate two protons per molecule. It is used in large amounts to ensure the reaction completes. Acids such as hydrochloric acid and phosphoric acid also are used in specific reactions.
Acidic hydrolysis is common in the hydrolysis of esters. Esters are compounds that form by the reaction of carboxylic acids with alcohol. When esters hydrolyze in the presence of an acid, it results in the formation of carboxylic acid and alcohol. Acidic hydrolysis also helps in the hydrolysis of nitriles and acetals. The hydrolysis of a nitrile with acid results in the formation of carboxylic acid and ammonia, while the hydrolysis of acetal results in the formation of a carbonyl compound and an alcohol.
One drawback of acidic hydrolysis is the controlling of reaction conditions in order to prevent side reactions and unwanted by-products. Another difficulty is handling highly corrosive and hazardous acids involved in the reaction.
What is Basic Hydrolysis
Basic hydrolysis is the use of a base to break down the chemical bond. This type of hydrolysis is useful in organic chemistry to break down amides, esters, nitriles, imines, and other functional groups.
In the mechanism of basic hydrolysis, a hydroxide ion is donated by the base to the molecule that should be hydrolyzed. This hydroxide ion acts as a nucleophile. It attacks the carbonyl carbon of the molecule that is hydrolyzed. This attack lowers the strength of the bond of the molecule.
The most common base used in basic hydrolysis is sodium hydroxide. This is a strong base. Other bases, such as potassium hydroxide or lithium hydroxide, also help in basic hydrolysis. Basic hydrolysis is useful in the hydrolysis of amides. It also helps to produce new compounds from precursors. In addition, it is helpful in the manufacture of soap.
In basic hydrolysis, the possibility of forming undesirable side reactions and undesirable by-products is minimum. Challenges associated with basic hydrolysis are controlling reaction conditions such as temperature, reaction time, and base concentration and handling the strong bases carefully.
Difference Between Acidic and Basic Hydrolysis
Definition
Acidic hydrolysis is a reaction that involves the use of an acid to break down a chemical bond, whereas basic hydrolysis is a reaction that involves the use of a base to break down the chemical bond.
Component Added
In acidic hydrolysis, a proton is added to the molecule that is being hydrolyzed, whereas in basic hydrolysis, a hydroxide ion is added to the molecule.
Compounds Broken
In acidic hydrolysis, the hydrolysis reaction mostly targets esters, amides, nitriles, and acetals, while in basic hydrolysis, the hydrolysis reaction mostly targets amides, esters, nitriles, and imines.
Uses
Acidic hydrolysis helps to break down esters, amides, nitriles, and acetals, whereas basic hydrolysis helps to break down esters, amides, nitriles, and imines. Basic hydrolysis also helps produce new compounds from precursors and soap.
Conclusion
In brief, hydrolysis is a process that breaks down a molecule into smaller components through a reaction with water. There are different types of hydrolysis. Acidic hydrolysis and basic hydrolysis are two such types of hydrolysis. The main difference between acidic hydrolysis and basic hydrolysis is that acidic hydrolysis involves the use of an acid to break down a chemical bond, whereas basic hydrolysis involves the use of a base to break down a chemical bond.
Reference:
1. “Acid Hydrolysis.” Science Direct.
2. “Basic Hydrolysis of Esters – Saponification.” Master Organic Chemistry
Image Courtesy:
1. “Acidic Ester Hydrolysis” By Jambels – Own work (CC BY-SA 4.0) via Commons Wikimedia
2. “Base catalyzed hydrolysis of parabens” By Pyager14 – Own work (CC BY-SA 4.0) via Commons Wikimedia
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