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Learn about the reaction between acetone and water as well as acetone and alcohol. Understand if acetone is soluble in water and if acetone has alcohol in it.Updated: 11/21/2023
Frequently Asked Questions
What happens when you mix water and acetone?
Acetone is a highly soluble molecule; it dissolves completely in water. The presence of the oxygen atom in acetone is the reason why acetone is able to form hydrogen bonds when it is mixed with water. This results in the dissolving of acetone and the formation of a hom*ogenous solution.
Why is acetone highly soluble in water?
Acetone is a small polar molecule that dissolves completely in water; its carbonyl group -CO is the sole contributor to its polarity. Oxygen is more electronegative than carbon, it draws the electrons closer; granting it a partial negative charge. The electrons are farther from carbon, and that grants it a partial positive charge.
Table of Contents
- What Is Acetone?
- Acetone and Water
- Acetone and Alcohol
- Acetone and Iodine
- Lesson Summary
Acetone is an organic compound that is composed of carbons, hydrogens, and oxygen. It is a colorless, volatile, and highly flammable liquid; its extreme volatility is the reason why this acetone must be stored in an air-tight container. The functional group of acetone is the carbonyl group {eq}-CO {/eq}, which is a carbon atom that is double bonding with an oxygen atom {eq}-C=O {/eq}. Functional groups serve as an indicator of the type of organic compounds; compounds that only have the carbonyl as a functional group are classified as ketones. Acetone is the simplest ketone; it is composed of two methyls attached to the central carbon in the carbonyl group. The molecular structure of acetone is depicted in Figures 1 and 2. The central carbon is {eq}sp^2 {/eq} hybridized, the bond angles between the carbon atoms are estimated to be equal to 120{eq}^{\circ} {/eq}. Acetone has a trigonal planar geometry.
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The condensed chemical formula for acetone is {eq}C_3H_6O {/eq}, its expanded formula can be written as {eq}(CH_3)_2CO {/eq} or {eq}CH_3COCH_3 {/eq}. Propanone or propan-2-one is acetone's systematic name. Acetone is categorized as a very weak acid; its pKa value is equal to 19.3 (the higher the pKa value, the weaker the acid. For comparison, HCl's pKa value is -7). The pKa value of water, which is a neutral compound, is around 15.74. The acidity of acetone is much smaller than that of water. That, however, does not make acetone a base. Acetone has a total of six donatable protons (three in each methyl). The structure of acetone is perfectly symmetrical; the hydrogen atoms are all identical and are all equally donatable. However, only one hydrogen atom can be removed from {eq}C_3H_6O {/eq} to form a conjugate base as depicted in Figure 3. Acetone gets deprotonated and its conjugate base gets stabilized if and only if it reacted with an extremely strong and bulky base, like 2,6-dimethyl pyridine.
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Acetone is a naturally occurring chemical compound that is found in nature in trees and plants. It is also found in small quantities in the gases rising from volcanic eruptions and forest fires. It is also found in tobacco smoke, exhaust gas, and in the human body; the body produces acetone when breaking down fats and lipids.
How to neutralize acetone? Acetone is a good solvent for some polymers (plastics). In the case of acetone, if a residue is present on a piece of plastic, the plastic can be rinsed with water to flush the acetone away and stop it from dissolving the plastic (gradually). The chemistry behind this is discussed in the following section.
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Table of Contents
- What Is Acetone?
- Acetone and Water
- Acetone and Alcohol
- Acetone and Iodine
- Lesson Summary
Is acetone soluble in water? What sort of reaction occurs between acetone and water? Water is a universal solvent that is characterized by being polar and abundantly available. The unique properties of water make it an excellent solvent for many solutes. Recall that like dissolves like; polar solvents dissolve polar solutes. Most organic compounds are known to be nonpolar and hydrophobic. But does acetone dissolve in water? Is acetone miscible in water? In order for acetone to be soluble in water, it has to have some degree of polarity. The carbonyl group is composed of an oxygen and a carbon atom. The electronegativity difference between these two atoms is significant. Oxygen, the more electronegative atom, draws the shared electron pairs closer; granting it a partial negative charge. Carbon is less electronegative; it possesses a partial positive charge because the electrons are closer to oxygen than they are to carbon. This uneven distribution of electrons makes acetone a polar molecule. The oxygen atom is also capable of forming hydrogen bonds with the neighboring water molecules; this leads to the formation of a hom*ogenous water and acetone solution. Acetone is miscible because it completely dissolves in water. Acetone dissolves in water to form geminal-diol is {eq}C_3H_8O_2 {/eq}.
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Is acetone alcohol? An alcohol is a polar organic compound whose functional group is the hydroxyl group {eq}-OH {/eq}. Seeing that the functional group of acetone is the carbonyl -CO and not the hydroxyl -OH, then it can be deduced that acetone cannot be an alcohol. Does acetone have alcohol in it? Acetone is used as a nail polish remover, its strong odor is quite similar to that of rubbing alcohol. This is why there is a misconception in thinking that acetone is or contains alcohol. Acetone and alcohol do react together to form new products. The product of mixing acetone and alcohol is hemiacetal, which is an organic compound with the general formula {eq}RR'COR'' {/eq}, where R is an alkyl group.
The oxygen in the alcohol's hydroxyl attacks the carbon in acetone's carbonyl, as shown in Figure 5.
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The acetone reaction with iodine follows the same mechanism that is depicted in Figure 6. In acetone's case, the R is replaced with a methyl group {eq}-CH_3 {/eq} and the X is replaced with the halogen iodine I. The type of reaction between acetone and iodine is called the haloform reaction, which is a reaction that involves acetone and a base and a halogen, which is iodine in this case. A halogen is an electronegative element from group 17 on the periodic table, as shown in Figure 7. The products of the iodination of acetone are an acid salt and iodoform.
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Acetone is a colorless, highly volatile liquid with a strong odor. It is often used as nail polish remover. Its distinct odor is quite similar to that of rubbing alcohol, which is why it is often mistaken as an alcohol. Acetone is one of the simplest ketones, which are organic compounds that have the carbonyl group {eq}-CO {/eq} as a functional group. A carbonyl consists of a carbon double bonding with an oxygen. The molecular structure of acetone shows a symmetrical compound with trigonal planar geometry. The carbonyl's carbon is {eq}sp^2 {/eq} hybridized. chemical formula for acetone is {eq}C_3H_6O {/eq}. Acetone is weakly acidic; it gets deprotonated in the presence of a strong and bulky base. Acetone is an organic molecule that occurs naturally in the human body when the body breaks down fats. It is also found in nature in the gas of forest fires and volcanos.
Acetone is miscible in water; it dissolves completely in water due to the polarity of its carbonyl group. Its partially negative oxygen atom forms hydrogen bonds with the water molecules; the resulting product from acetone and water is the geminal diol. Acetone can react with alcohol, which is an organic molecule with the hydroxyl {eq}-OH {/eq} functional group, to form hemiacetal. The iodination of acetone is a haloform reaction. Such reactions involve a ketone, a base, and a halogen reacting to form an acid salt, and iodoform are formed.
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Video Transcript
What Is Acetone?
Let's say that the color of the nail polish you just bought looks awful. Sure, it looked good in the bottle, but it looks terrible on your fingernails. But don't panic, just remove it with some acetone. Or let's say you're in the chemistry lab and need your glassware cleaned. All you've got to do is the same thing--grab some acetone! Or let's say you have a band and it needs a name. You can copy the Los Angeles rock group from 1992 who named their band (you guessed it) Acetone!
Okay, okay, let's forget about the rock band and focus on the chemical. Acetone is a colorless, flammable, liquid, organic compound (meaning it contains carbon) that has a carbon double bonded to an oxygen as well as other carbon and hydrogen atoms. Acetone is a type of ketone, which is an organic molecule that has a carbonyl group (but more on that later).
Acetone's claim to fame is that it's a great solvent, meaning it can dissolve other substances. This is due to its chemical makeup. Let's explore how acetone mixes with some substances like water, alcohol, and iodine.
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Acetone and Water
Acetone is able to fully dissolve in water, meaning it's miscible in water. Initially, that probably doesn't sound impressive, but many organic compounds don't mix well with water.
So how is acetone able to mix with water? For starters, acetone is small, which helps, but there's more. Acetone has a carbonyl group, which is a carbon double bonded to an oxygen.
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This carbonyl group is polar, meaning the compound has a slight charge. As a general rule, polar molecules can dissolve in polar molecules. Since water is polar, and acetone is polar due to the carbonyl group, they can mix.
Acetone and Alcohol
So what about alcohol and acetone? Alcohol is an organic compound that is polar, like acetone. It has an oxygen bonded to a hydrogen as its distinguishing feature.
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When acetone is mixed with an alcohol, it can produce a hemiacetal (sometimes spelled 'hemiketal').
Because acetone is polar, the oxygen on the carbonyl group is slightly negative and the carbon is slightly positive. The alcohol is also polar, with the oxygen being slightly negative. The negative oxygen on the alcohol goes after the slightly positive carbon on the carbonyl group. The eventual result is the hemiacetal.
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Acetone and Iodine
The last reaction we will look at is called a haloform reaction, which is where a ketone is mixed with a halogen and a base. The result is a carbonyl group and a haloform.
Whoa! Let's unpack all those words! Wondering what a halogen is? Take a look at the periodic table and find group 17…those are all halogens. We'll focus on iodine here, but this process works with other halogens, too. A haloform is a halogen that's attached to a carbon and three hydrogen atoms.
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This reaction begins by exposing the ketone to a base, which removes one of its hydrogen atoms. Once it's removed, the ketone reacts with the iodine. In the case of an acetone, the R would be a carbon and three hydrogen atoms. The X refers to the halogen (in this case iodine).
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Lesson Summary
Let's take a couple moments to review what we've learned. Acetone is a colorless, liquid, organic compound. It's a type of ketone, which is an organic molecule that has a carbonyl group. A carbonyl group is a carbon double bonded to an oxygen. We focused on mixing acetone with three different substances.
- Acetone can dissolve in water (meaning it's miscible). This is because both water and acetone are polar, meaning they have a slight charge.
- Acetone reacts with alcohol, which is an organic compound with oxygen bonded to hydrogen, to form a hemiacetal. In this reaction, the oxygen on the alcohol goes after the carbon on the carbonyl group.
- Acetone reacts with halogens, like iodine, in haloform reactions, which is where a ketone is mixed with a halogen and a base. Here, a ketone (like acetone) is exposed to a base, which removes hydrogen. The ketone then reacts with the halogen.
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