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Ch. 22 - Condensation ChemistryWorksheetSee all chapters
All Chapters
Ch. 1 - A Review of General Chemistry
Ch. 2 - Molecular Representations
Ch. 3 - Acids and Bases
Ch. 4 - Alkanes and Cycloalkanes
Ch. 5 - Chirality
Ch. 6 - Thermodynamics and Kinetics
Ch. 7 - Substitution Reactions
Ch. 8 - Elimination Reactions
Ch. 9 - Alkenes and Alkynes
Ch. 10 - Addition Reactions
Ch. 11 - Radical Reactions
Ch. 12 - Alcohols, Ethers, Epoxides and Thiols
Ch. 13 - Alcohols and Carbonyl Compounds
Ch. 14 - Synthetic Techniques
Ch. 15 - Analytical Techniques: IR, NMR, Mass Spect
Ch. 16 - Conjugated Systems
Ch. 17 - Aromaticity
Ch. 18 - Reactions of Aromatics: EAS and Beyond
Ch. 19 - Aldehydes and Ketones: Nucleophilic Addition
Ch. 20 - Carboxylic Acid Derivatives: NAS
Ch. 21 - Enolate Chemistry: Reactions at the Alpha-Carbon
Ch. 22 - Condensation Chemistry
Ch. 23 - Amines
Ch. 24 - Carbohydrates
Ch. 25 - Phenols
Ch. 26 - Amino Acids, Peptides, and Proteins
Ch. 26 - Transition Metals
Condensation Reactions
Aldol Condensation
Directed Condensations
Crossed Aldol Condensation
Claisen-Schmidt Condensation
Claisen Condensation
Intramolecular Aldol Condensation
Conjugate Addition
Michael Addition
Robinson Annulation
Additional Guides
Johnny Betancourt

Hydrolysis is the cleavage of a molecule into two smaller molecules through hydration. The combination of smaller molecules into a larger molecule can be accomplished through dehydration.

Hydrolysis mechanism

Let’s take a look at the synthesis of acetic acid through addition of water to ethyl acetate in acidic media:

Acid hydrolysis of esterAcid hydrolysis of ester

This mechanism shows how water breaks the bond between the carbonyl carbon and the ethoxy group. Notice that I used equilibrium arrows throughout the mechanism. It’s completely reversible through dehydration! Of course, this was just an example of hydrolysis in low pH; basic hydrolysis of an ester, called saponification, is also possible. 

Where else does this occur?

Other polymers, like those produced through condensation reactions, can also be broken down into monomers through hydration. Amides, salts, and polysaccharides can also be hydrolyzed. Let’s see what our products are when cellubiose is hydrolyzed:

Hydrolysis of cellubioseHydrolysis of cellubiose

We started off with one molecule, cellubiose, and added water to it to end up with two glucose molecules. I’ve color-coded where that added water ended up in the two molecules. Another example of a disaccharide being broken down in nature is sucrose being hydrolyzed into glucose and fructose in the human body; starch can be also be broken down into glucose monomers. 

Johnny Betancourt

Johnny got his start tutoring Organic in 2006 when he was a Teaching Assistant. He graduated in Chemistry from FIU and finished up his UF Doctor of Pharmacy last year. He now enjoys helping thousands of students crush mechanisms, while moonlighting as a clinical pharmacist on weekends.