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Solvolysis: Hydrolysis, Alcoholysis & Ammonolysis

Instructor: Korry Barnes

Korry has a Ph.D. in organic chemistry and teaches college chemistry courses.

How can a solvent be used as part of a chemical reaction? This lesson will focus on the general process of solvolysis by specifically using the reactions called hydrolysis, alcoholysis, and ammonolysis as examples.

Not Just Used for Cleaning

Did you ever have the pleasure of being in charge of cleaning the bathroom when you were young? Unfortunately it's a necessary evil, and most parents can't wain until their children are old enough to be in charge of their own facilities.

When you clean your bathroom you always use some sort of cleaning solvent right? Solvents that are commonly used for cleaning agents might include ammonia, bleach, or some other type of detergent or surfactant.

Did you know however that solvents aren't just used for household cleaners? They find a lot of use in various chemical reactions as well, especially in reactions involving organic compounds. Let's see how a solvent can actually be used as part of a chemical reaction in a process called solvolysis.

What is Solvolysis?

Let's get started by considering the process of solvolysis in a broad context. Recall that a nucleophile is anything that can act as an electron pair donor in a chemical reaction and form new bonds via the lone pair. In organic chemistry, nucleophiles always react with electrophiles, which are electron pair acceptors.

In general, solvolysis is a type of substitution or elimination reaction in which the solvent acts as a nucleophile.

In a solvolysis reaction there is usually an alkyl halide (an organic substrate containing a halogen) that acts as the electrophile and a solvent molecule that acts as the nucleophile. For example, a tertiary benzyl chloride will undergo a solvolysis reaction in which water acts as both the solvent and the nucleophile. This is a substitution process in which the chlorine atom is replaced by a hydroxyl (-OH) group.


The solvolysis of a tertiary benzyl chloride with water
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Let's now move into talking about some of the specific types of solvolysis reactions that are out there.

Hydrolysis

When an organic compound reacts with water in some way, it's called a hydrolysis reaction. A good example is the reaction of a molecule known as succinic anhydride reacting with water.


The reaction of succinic anhydride with water is a hydrolysis reaction
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Notice how the starting material (succinic anhydride) is a ring structure, but once the reaction with water happens, two of the carbon-oxygen bonds are broken within the ring and two new carbon-oxygen bonds are formed in the product. A good way to remember this concept is by remembering that 'hydro-' means 'water.'

Alcoholysis

If hydrolysis is an organic compound reacting with water, what do you think alcoholysis might be? If you were thinking about a reaction involing an alcohol, you would be correct! Alcoholysis is defined as a reaction that occurs between an organic molecule and an alcohol of some sort.

The handy thing about alcoholysis is that it's virtually identical to hydrolysis, the only difference is that it involves using an alcohol as the nucleophile instead of a water molecule. An example is the reaction of the tert-butyl chloride with methanol to give methyl tert-butyl ether as the product.

Note that any alcoholysis reaction will always form an ether as the reaction product. Ethers are simply derivatives of water in which the two hydrogen atoms have been replaced with two carbon-based groups. Notice the methyl and tert-butyl groups associated with methyl tert-butyl ether.


Methyl tert-butyl ether is an example of an ether, the product formed from an alcoholysis reaction
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Ammonolysis

Have you ever had the pleasure of smelling a cleaning solution that's made from ammonia? It's quite the pungent odor! It turns out however that ammonia can be utilized in a solvolysis reaction too.

Ammonolysis is when ammonia acts as the nucleophile and reacts with an organic compound. The beginning of the term should help us remember that it's ammonia we're dealing with here.

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