What is a Tautomerization ? – Definition, Mechanism & Example


The maximum famous tautomerization is the enol and keto tautomers. With this form of tautomerization, we use a ketone or a molecule with a carbon double bonded to an oxygen. Although we commonly display ketones on this manner, in reality, an answer of ketones can be switching backward and forward in speedy equilibrium with any other shape, the enol. The enol movements a hydrogen from the alpha carbon onto the oxygen, shifting the carbon-oxygen double bond to a carbon-carbon double bond.

Molecules Like Musical Chairs

When you had been younger, did you ever play the sport known as musical chairs? People stroll round as a few track is gambling and while the track stops, absolutely each person attempts to take a seat down down in a chair. Whomever does not get a chair is then removed from the sport. The gamers get rearranged in the course of the sport and seldom grow to be withinside the equal chair they began out in.

Did you understand that we will liken a few molecules to the sport musical chairs? Although it could appear difficult to believe, every so often the atoms in a molecule will rearrange themselves, similar to in the sport, to shape a distinctive structure. This form of system is known as tautomerization and is the concern of our lesson today. We are going to be searching on the definition of tautomers, a selected examples of tautomers, and the mechanism via way of means of which they interconvert. Let’s play musical molecules!


Let’s kick matters off via way of means of searching at a few definitions. In natural chemistry constitutional isomers are compounds which have the equal chemical formula; that is, they are made from the equal atoms however range of their atom connectivities. Tautomers are constitutional isomers of compounds that conveniently interconvert among each other. Take, for instance, the 4 constitutional isomers of butanol.

Notice how all the systems are associated within side the feel that they’ve the equal numbers of carbon, hydrogen, and oxygen atoms, however they range in how the atoms are bonded together. Tautomers are a type of constitutional isomer that have a tendency to arrange from one shape to the alternative rapidly.


Now that we are a piece greater acquaint with what it’s far we are searching for. Let’s examine multiple examples of compounds which can tautomers of each other. Take, for instance, the tautomers of the molecule referred to as phenol. Note how they’re distinctive from each other the placement of each the atoms and the chemical bonds.

One of the systems has 3 double bonds in the ring device and an alcohol useful group. At the same time as the alternative most effective carries double bonds relate to the hoop and a ketone. The carbon-oxygen double bond useful group. Make positive to remember. Though, that the systems nonetheless have the equal chemical formula. They simply have distinctive atom arrangements.

Another true instance of tautomers are the systems refer to as thiolactam and thiolactim respectively. Can you see the distinction among those compounds? If you observed that one compound carries a carbon-sulfur double bond. Additionally one carries most effective a carbon-sulfur unmarried bond, you are at the proper track!

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