Log In Start studying!

Select your language

Suggested languages for you:

Select your language

Suggested languages for you:
StudySmarter - The all-in-one study app.
4.8 • +11k Ratings
More than 3 Million Downloads
Free
|
|

Carboxylic Acids

Carboxylic Acids

Vinegar, be it the malt vinegar you shake over your chips or that balsamic vinegar you stir into a salad dressing, is generally 5-8% acetic acid by volume. It has a sharp, astringent taste and a low pH. Acetic acid is scientifically known as ethanoic acid and is one of the most common carboxylic acids. It is quite simple to make. Leave a bottle of apple cider out in the sun and before too long, naturally occurring Acetobacter bacteria start turning the ethanol present into acetic acid. But what actually is a carboxylic acid?

  • This article is an introduction to carboxylic acids in organic chemistry.
  • To start, we'll define carboxylic acid and explore both the carboxylic acid functional group and general structure.
  • After that, we'll look at examples of carboxylic acids.
  • We'll then look at carboxylic acid nomenclature before moving on to explore their properties and acidity.
  • We'll also touch on carboxylic production and reactions of carboxylic acids, including the test for carboxylic acids.

Carboxylic acid definition

Carboxylic acids are organic molecules with the carboxyl functional group, -COOH.

Carboxylic acid functional group

The definition above tells us that carboxylic acids all contain the carboxyl functional group, -COOH. This group is made up of two other functional groups:

  • The hydroxyl group found in alcohols, -OH,
  • The carbonyl group found in aldehyde and ketones, C=O.

Carboxylic acid general formula

The combination of the hydroxyl and carbonyl functional groups gives carboxylic acids the general formula RCOOH.

Carboxylic Acids general structure StudySmarter

The general structure of a carboxylic acid is shown with the carbonyl group circled in blue and the hydroxyl group circled in red. StudySmarter Originals

Look at the general structure of a carboxylic acid, shown above. We know that a carbon atom can only form four covalent bonds because it has just four outer shell electrons. The carboxyl functional group takes up three of these electrons: two form a C=O double bond with the oxygen atom and one bond with the hydroxyl group, -OH. This means that the carbon atom has just one electron remaining that it can use to form a bond. This means that it can only bond to one other R group, be it a long complex chain or just a simple hydrogen atom. Regardless of the R group, this arrangement means that the carboxylic acid functional group must always be at the end of a hydrocarbon chain.

Examples of carboxylic acids

Carboxylic acids range from simple molecules like methanoic acid, which has just one carbon atom, to complex molecules that are tens of carbon atoms long. Below, you'll find a table giving both the common and IUPAC names of some of the smaller carboxylic acids.

Common nameIUPAC nameNumber of carbon atoms
Formic acidMethanoic acid1
Acetic acidEthanoic acid2
Propionic acidPropanoic acid3
Butyric acidButanoic acid4
Valeric acidPentanoic acid5
Caproic acidHexanoic acid6

Other examples of carboxylic acids include all Amino Acids, from the smallest amino acid, glycine, to the largest, tryptophan. Fatty acids are carboxylic acids as well. You might have heard of omega 3 and omega 6, two essential nutrients. They're both fatty acids; therefore, they are carboxylic acids.

Carboxylic acids glycine StudySmarter The amino acid glycine.commons.wikimedia.org

Carboxylic acids tryptophan StudySmarter

The amino acid tryptophan.
commons.wikimedia.org

By looking at the common names of many carboxylic acids, you can take a guess as to where they come from. The Latin word capra means goat, so caproic acid is found in goat fat. Myristic acid, a carboxylic acid with 14 carbon atoms, comes from nutmeg - an aromatic spice in the family Myristica.

Carboxylic acid nomenclature

Carboxylic acids are named using standard IUPAC nomenclature (check out Organic Nomenclature if this is your first look at naming organic molecules). The methodical IUPAC system makes naming carboxylic acids pretty simple, really. Let's take a quick look at some of the rules.

  • Carboxylic acids have the suffix -oic acid.
  • We use the standard root names to show the length of the molecule.
  • We show additional functional groups and side chains using prefixes and numbers to indicate their position on the carbon chain, counting the carbon atom in the -COOH functional group as carbon 1.

These tables should give you a quick reminder of the different root names and prefixes used to name molecules.

Length of carbon chainRoot name
1-meth-
2-eth-
3-prop-
4 -but-
Functional group presentPrefix
-Clchloro-
-Brbromo-
-Iiodo-
-OHhydroxy-
-NH2amino-

Let's look at an example.

Name this carboxylic acid.

Carboxylic acids nomenclature example 2-chloropropanoic acid StudySmarterAn unknown carboxylic acid. StudySmarter Originals

This molecule's carbon chain is three atoms long, so we know it takes the root name -prop-. It also contains a chlorine atom. We therefore need to use the prefix chloro-. Remember that we count the carbon atom that is part of the carboxyl group as carbon 1, so in this case, the chlorine atom is attached to carbon 2. We call this molecule 2-chloropropanoic acid.

Carboxylic acids nomenclature example 2-chloropropanoic acid StudySmarter2-chloropropanoic acid, labelled. StudySmarter Originals

Properties of carboxylic acids

Take a closer look at the -COOH group. As we know, it contains not only the carbonyl functional group, C=O, but also the hydroxyl functional group, -OH. Let's draw these both out.

Note that we've drawn the hydroxyl group in full; the reason for this will become clear in just a second.

Carboxylic Acids general structure StudySmarterThe general structure of a carboxylic acid. StudySmarter Originals

If we look at a table of electronegativities, we can see that oxygen is a lot more electronegative than both carbon and hydrogen.

ElementElectronegativity
H2.20
C2.55
N3.04
O3.44
F3.98
Cl3.16

What does that mean? Well, electronegativity is an atom's ability to attract a shared or bonding pair of electrons towards itself. In this case, both of the oxygen atoms in the -COOH group pull on the electrons they use to bond to the other carbon and hydrogen atoms, tugging the electrons closer to themselves. This makes the two oxygen atoms partially negatively charged and leaves the carbon and hydrogen atoms partially positively charged. The bonds are now polar. We label them using the delta symbol, δ.

You can see the partial charges in the diagram below, as well as the oxygen atoms' lone pairs of electrons.

Carboxylic Acids partial charges polarity StudySmarterCarboxylic acid partial charges. StudySmarter Originals

In fact, the O-H bond in carboxylic acids is so polar, due to the different electronegativities of oxygen and hydrogen, that carboxylic acids can form hydrogen bonds.

  • In an OH bond, the oxygen atom attracts the shared pair of electrons towards itself quite strongly.
  • This leaves the hydrogen atom with a partial positive charge.
  • Because the hydrogen atom is so small, the charge is densely concentrated.
  • The hydrogen atom is attracted to one of the lone pairs of electrons on an oxygen atom belonging to a neighbouring molecule.
  • This is a hydrogen bond.

Carboxylic Acids hydrogen bonding StudySmarterCarboxylic acid hydrogen bonding. StudySmarter Originals

Check out Intermolecular Forces for a more in-depth explanation of hydrogen bonds.

Hydrogen bonds are relatively strong. They influence many of the properties of carboxylic acids.

Melting and boiling points

Carboxylic acids have higher melting and boiling points than similar alkanes and aldehydes. As we now know, this is because carboxylic acids form hydrogen bonds between molecules. In contrast, the strongest intermolecular forces between aldehydes are permanent dipole-dipole forces, whilst the strongest forces between alkanes are van der Waal forces. Hydrogen bonds are much stronger than both permanent dipole-dipole forces and van der Waal forces, and so require more energy to overcome.

Additionally, carboxylic acids have higher melting points than similar alcohols, despite alcohols also forming hydrogen bonds. This is because two carboxylic acids can form hydrogen bonds in a certain way to produce a molecule called a dimer. We can consider a dimer as two carboxylic acid molecules joined together to form one larger molecule. This means that it experiences double-strength van der Waals forces. On the other hand, alcohols don't form these dimers.

Carboxylic acids intermolecular forces dimer melting boiling point StudySmarter Two ethanoic acid molecules create a dimer by hydrogen bonding with each other. StudySmarter Originals

Solubility

Carboxylic acids can also form hydrogen bonds with water. This makes shorter chain carboxylic acids soluble in aqueous solutions. However, long chain molecules are insoluble because their non-polar hydrocarbon chains get in the way of hydrogen bonding, breaking the bonds up. Imagine using a magnet to pick up iron filings. If you put something in between the magnet and the filings, such as a block of wood, you won't be able to pick as many up - the strength of the attraction has decreased.

Acidity of carboxylic acids

Carboxylic acids, as their name suggests, are acids.

An acid is a proton donor.

To be more specific, carboxylic acids are weak acids.

A weak acid is an acid that only partially dissociates in solution. In contrast, strong acids fully dissociate in solution.

Head over to Acids and Bases for more about strong and weak acids.

In solution, carboxylic acids form an equilibrium, where some of the molecules dissociate into a positive hydrogen ion and a negative carboxylate ion, and some remain intact.

RCOOH ⇌ RCOO- + H+

Because carboxylic acids are so weak, the equilibrium lies well to the left. This means that only a few of the molecules dissociate. And because carboxylic acids are acids, they have a pH below 7. They take part in many typical acid-base reactions, which we'll introduce you to later.

Relative acidity of carboxylic acids, alcohols and phenol

Carboxylic acids are weak acids because their hydroxyl group (-OH) gives up a proton (which is just a hydrogen ion) in solution. You might consequently wonder why other molecules that have the same hydroxyl functional group, such as alcohols (ROH) and phenols (C6H5OH), aren't acidic. To understand this, we need to consider two factors:

  • The strength of the O-H bond.

  • The stability of the negative ion formed.

Bond strength

The O-H bond in carboxylic acids is much weaker than the O-H bond in alcohols and phenol. This is all thanks to the carboxylic acid's other functional group, the carbonyl group (C=O). The carbonyl group is electron-withdrawing, meaning that it attracts the shared pair of electrons in the O-H bond over towards itself, weakening the O-H bond. A weaker O-H bond means that it is easier for carboxylic acids to lose hydrogen as an H+ ion, and therefore gives them a greater acidity.

However, alcohols and phenol lack an electron-withdrawing group, and so their O-H bonds are just as strong as ever.

Ion stability

Let’s now think about the ion formed when carboxylic acids, alcohols and phenol act as acids by losing a proton (a hydrogen ion, H+). The more stable this ion, the less readily it joins back up with a hydrogen ion, and the greater the acidity of the original molecule.

When carboxylic acids lose a proton, they form negative carboxylate ions, RCOO-. The negative charge delocalises across both carbon-oxygen bonds. Instead of having one C-O single bond and one C=O double bond, the carboxylate ion has two identical carbon-oxygen bonds, which are each equivalent in strength to a one-and-a-half bond. Delocalisation is great for the ion - it stabilises the molecule, and makes oxygen’s electrons much less available for joining back up with a hydrogen ion.

However, alcohols and phenols don't form such a stable negative ion. When alcohols ionise, they form the alkoxide ion, RO-. This is a very unstable ion. Firstly, the R group tends to be a hydrocarbon chain, which is electron-donating and so increases the oxygen’s electron density. Secondly, the negative charge can’t delocalise and so is concentrated on the oxygen atom. All in all, this makes for a reactive ion that can’t wait to join back up with a hydrogen ion to form an alcohol again.

When phenols ionise, they form the phenoxide ion, C6H5O-. Like with the carboxylate ion, the negative charge delocalises; in this case, it delocalises across the enitre benzene ring. Once again, delocalisation makes the ion more stable, and so phenol is a stronger acid than alcohols. But the delocalisation in phenoxide ions is weaker than the delocalisation in carboxylate ions because it is spread over less electronegative carbon atoms. This means that oxygen in phenoxide ions still keeps most of its negative charge and is more attractive to H+ ions than oxygen in carboxylate ions. All in all, phenol is a stronger acid than alcohols, but a weaker acid than carboxylic acids.

Carboxylic Acids relative acidity of carboxylic acid alcohol phenol StudySmarterThe stability of the resulting ion formed plays a role in the acidity of carboxylic acids, alcohols and phenol. StudySmarter Originals

Relative acidity of different carboxylic acids

Acidity also varies between different carboxylic molecules. We'll explore the trends in acidity in carboxylic acids with varying chain lengths and different numbers of chlorine substituents.

Chain length

Increasing the length of the carboxylic acid's hydrocarbon R group, by adding additional -CH2- groups, decreases the strength of the acid. The longer the hydrocarbon chain, the weaker the acid. This is because alkyl groups are electron-donating. They push electrons away from themselves and increase the strength of the O-H bond. This makes it harder for the -COOH group to give up a hydrogen ion. It also increases the charge density of the resulting carboxylate ion's -COO- group, making it easier for the ion to bond to H+ again.

Chlorine substitutents

Swapping some of the hydrogen atoms in the carboxylic acid's R group for electron-withdrawing groups, such as electronegative chlorine atoms, increases the strength of the acid. The more chlorine substituents, the stronger the acid. This is because electron-withdrawing groups like chlorine atoms pull electrons away from the -COOH group, weakening the O-H bond and making it easier for the carboxylic acid to lose a hydrogen ion. These groups also decrease the charge density of the resulting carboxylate's -COO- group, making it harder for the ion to bond to H+ again.

Carboxylic Acids relative acidity chain length chlorine substituents StudySmarterThe effect of chain length and chlorine substituents on the relative acidity of carboxylic acids. StudySmarter Originals

Carboxylic acid production

At the start of this article, we mentioned how if you leave cider out in the sun, it eventually turns into vinegar. Cider is an alcohol. In this reaction, it is oxidised into first an aldehyde and then a carboxylic acid. Oxidation is one way of producing carboxylic acids.

Oxidation

In the lab, we typically produce carboxylic acids through oxidation by heating a primary alcohol under reflux with an oxidising agent such as acidified potassium dichromate (K2Cr2O7) . Reflux prevents the aldehyde first formed from evaporating off, and allows it to react further into a carboxylic acid.

Carboxylic Acids Reflux StudySmarterEquipment setup for reflux, StudySmarter Originals

For example, reacting ethanol (CH3CH2OH) with acidified potassium dichromate produces first ethanal (CH3CHO), and then ethanoic acid (CH3COOH) :

CH3CH2OH + 2[O] CH3COOH + H2O

We use [O] to represent an oxidising agent.

Likewise, oxidising butanol (CH3CH2CH2CH2OH) gives butanoic acid (CH3CH2CH2COOH):

CH3CH2CH2CH2OH + 2[O] CH3CH2CH2COOH + H2O

The alcohol used must be a primary alcohol. Oxidising a secondary alcohol produces a ketone whilst tertiary alcohols cannot be oxidised at all. This is because oxidising a tertiary alcohol would involve breaking a strong C-C bond. It just isn't energetically favourable to do that, so no reaction occurs.

Check out Oxidation of Alcohols for a more detailed look at oxidation reactions.

You can make vinegar out of any sort of alcohol. For example, oxidising beer produces a rich and intense malt vinegar, whilst oxidising white wine produces a fruity wine vinegar. To make it yourself, first dilute your chosen alcohol to 10% abv in a large container. Mix in a source of Acetobacter, such as a live vinegar, i.e., one containing a living culture of bacteria. Cover the container with a fine muslin cloth and leave in a warm, dark place for a couple of months, tasting every week or so to see how it is getting along. Before too long, you'll have a unique, flavourful vinegar on your hands!

Other methods

Oxidation isn't the only way of producing carboxylic acids. You're likely to come across a few other methods during your organic chemistry journey. These include:

  • Hydrolysis of nitriles using either a dilute acid, or a dilute alkali followed by acidification.
  • Hydrolysis of esters using either a dilute acid, or a dilute alkali followed by acidification.
  • Electrophilic addition-elimination reaction of acyl chlorides with water.
  • Electrophilic addition-elimination reaction of acid anhydrides with water.

Find out more about these reactions in Nitriles, Reactions of Esters, and Acylation respectively. However, we also provide additional information about them in Reactions of Carboxylic Acids.

Reactions of carboxylic acids

Carboxylic acids react in multiple ways, thanks to their polar -COOH group. Some examples include:

  • Nucleophilic substitution, when a nucleophile attacks the partially positively charged carbon atom. You should remember that a nucleophile is an electron pair donor with a lone pair of electrons and negative or partially negative charge. This can form a whole range of products known as acid derivatives, such as acyl chlorides and acid anhydrides.

  • Esterification, another type of nucleophilic substitution reaction, where the nucleophile is an alcohol. This forms an ester.

  • Addition reactions across the C=O bond.

  • Neutralisation reactions, in which the molecule acts as an acid and a hydrogen ion is lost from the -OH group. This process forms a salt.

You can see many of these in more detail in Reactions of Carboxylic Acids.

Testing for carboxylic acids

To test for carboxylic acids, we rely on their behaviour as an acid. Carboxylic acids react with carbonates to form a salt, water, and carbon dioxide gas, whilst most other organic molecules won't react at all. Gas bubbling up through the test tube is a tell-tale sign of a reaction.

For example, reacting ethanoic acid with sodium carbonate forms sodium ethanoate, water, and carbon dioxide:

2CH3COOH(aq) + Na2CO3(aq) → 2CH3COONa(aq) + CO2(g) + H2O(l)

Carboxylic Acids - Key takeaways

  • Carboxylic acids have the general formula RCOOH and contain both the carbonyl and hydroxyl functional groups.
  • We name carboxylic acids using the suffix -oic acid.
  • Carboxylic acids are polar molecules. Because they contain a hydrogen atom bonded to an oxygen atom, they also experience hydrogen bonding.
  • Carboxylic acids have higher melting and boiling points than similar alkanes, aldehydes, and alcohols due to the nature of their hydrogen bonds.
  • Carboxylic acids are weak acids. They are more acidic than other molecules featuring the hydroxyl group, such as alcohols and phenol. Their acidity depends on additional electron-withdrawing groups, such as chlorine atoms, and the length of their hydrocarbon R group.
  • Carboxylic acids are typically produced through the oxidation of a primary alcohol.
  • Carboxylic acids can react in multiple ways, including as an acid, in addition reactions, and in reactions involving nucleophiles.

Frequently Asked Questions about Carboxylic Acids

Carboxylic acids are organic molecules containing the carboxyl functional group, -COOH. This consists of the hydroxyl group, -OH, and the carbonyl group, C=O.

Carboxylic acids are weak acids because they only partially dissociate in solution. They form an equilibrium, where some of the molecules ionise into positive hydrogen ions and negative carboxylate ions, and some remain intact. 

Carboxylic acids are formed by oxidising primary alcohols. To do this, heat a primary alcohol under reflux with an oxidising agent such as acidified potassium dichromate. The alcohol will first oxidise into an aldehyde before turning into a carboxylic acid.

All amino acids, the building blocks of proteins, are carboxylic acids. Another example is ethanoic acid, found in all types of vinegar.  Citric acid is also a carboxylic acid. 

To make an ester, you can react a carboxylic acid and an alcohol together in an esterification reaction, using a strong acid catalyst.

Final Carboxylic Acids Quiz

Question

Name the two functional groups present in carboxylic acids.

Show answer

Answer

The carbonyl group

Show question

Question

What suffix is used to name carboxylic acids according to IUPAC nomenclature?

Show answer

Answer

-oic acid

Show question

Question

Which molecule has a higher boiling point? Justify your answer.

Show answer

Answer

Propane (Mr = 44)

Show question

Question

Which molecule has a higher boiling point? Justify your answer.

Show answer

Answer

Hexanoic acid (Mr = 116)

Show question

Question

Explain why carboxylic acids have higher boiling points than similar mass aldehydes.


Show answer

Answer

  • Aldehydes cannot form hydrogen bonds with each other as they don’t contain a hydrogen atom bonded to an oxygen atom. Their strongest intermolecular forces are permanent dipole-dipole forces.
  • Carboxylic acids do form hydrogen bonds between molecules as they contain an O-H bond. 
  • Hydrogen bonds are stronger than permanent dipole-dipole forces and require more energy to overcome.

Show question

Question

Explain why short chain carboxylic acids are soluble in water.


Show answer

Answer

They can form hydrogen bonds with water molecules.

Show question

Question

As chain length increases, the solubility of carboxylic acids _____.


Show answer

Answer

Decreases

Show question

Question

Name some reaction types carboxylic acids can take part in.


Show answer

Answer

  • Neutralisation
  • Addition reactions
  • Esterification
  • Nucleophilic substitution

Show question

Question

Carboxylic acids can be formed from secondary alcohols. True or false? 

Show answer

Answer

False

Show question

Question

Oxidising a primary alcohol gives:

Show answer

Answer

An aldehyde

Show question

Question

All carboxylic acids are ____ acids.

Show answer

Answer

Weak

Show question

Question

Name the first three carboxylic acids with the shortest carbon chain lengths.

Show answer

Answer

  • Methanoic acid.
  • Ethanoic acid.
  • Propanoic acid.

Show question

Question

Name the functional group found in carboxylic acids.


Show answer

Answer

The carboxyl group.

Show question

Question

The carboxyl functional group is made up of two other functional groups. Which groups are these?


Show answer

Answer

Hydroxyl group

Show question

Question

Why are carboxylic acids described as weak acids?


Show answer

Answer

They only partially dissociate in aqueous solution.

Show question

Question

Give three reactions that carboxylic acids partake in that are typical of acids.


Show answer

Answer

  • Neutralisation reactions with carbonates and hydroxides.
  • Reaction with ammonia.
  • Reaction with metals.

Show question

Question

Name the salt produced when sodium hydroxide reacts with ethanoic acid.


Show answer

Answer

Sodium ethanoate

Show question

Question

Name the salt produced when magnesium reacts with butanoic acid.


Show answer

Answer

Magnesium butanoate

Show question

Question

Write a word equation for the reaction between a carboxylic acid and one other reagent to form an ester and one other product.


Show answer

Answer

Carboxylic acid + alcohol ↔ ester + water

Show question

Question

What conditions are required for esterification?

Show answer

Answer

  • Heat
  • Strong concentrated acid catalyst.

Show question

Question

Name the ester produced when ethanoic acid reacts with methanol with a strong acid catalyst.


Show answer

Answer

Methyl ethanoate

Show question

Question

Name the alcohol and carboxylic acid used to produce ethyl propanoate.


Show answer

Answer

Ethanol

Show question

Question

Carboxylic acids can be attacked by nucleophiles. Which part of the molecule will the nucleophile attack? 


Show answer

Answer

The partially positively charged carbon.

Show question

Question

Decarboxylating a carboxylic acid gives _____ and _____.

Show answer

Answer

An alkane

Show question

Question

Reducing a carboxylic acid gives _____.

Show answer

Answer

A primary alcohol and water.

Show question

Question

How do you make acid derivatives?

Show answer

Answer

React carboxylic acids with phosphorus(V) chloride or phosphorus(III) chloride.

Show question

Question

Describe how you produce carboxylic acids from nitriles using a dilute acid.

Show answer

Answer

Heat under reflux using a dilute acid catalyst. This produces a carboxylic acid and an ammonium salt.

Show question

Question

Describe how you produce carboxylic acids from nitriles using a dilute alkali.

Show answer

Answer

Heat under reflux with a dilute alkali. This produces a carboxylate salt and ammonia. Adding a strong acid frees up the carboxylic acid.

Show question

Question

Describe how you produce carboxylic acids from esters using a dilute acid.

Show answer

Answer

Heat under reflux with an excess of a dilute acid catalyst. This produces a carboxylic acid and an alcohol. 

Show question

Question

Describe how you produce carboxylic acids from esters using a dilute alkali.

Show answer

Answer

Heat under reflux with a dilute alkali. This produces a carboxylate salt and an alcohol. Adding a strong acid turns the carboxylate salt into a carboxylic acid.

Show question

Question

Which of the following are ways of making carboxylic acids?

Show answer

Answer

Hydrolysing esters

Show question

Question

Name two carboxylic acids that can be oxidised.

Show answer

Answer

  • Methanoic acid
  • Ethanedioic acid

Show question

Question

Which oxidising agents can we use to oxidise methanoic acid?

Show answer

Answer

Just Tollens' reagent and Fehling's solution.

Show question

Question

Which oxidising agents can we use to oxidise ethanedioic acid?

Show answer

Answer

Just acidified potassium dichromate.

Show question

60%

of the users don't pass the Carboxylic Acids quiz! Will you pass the quiz?

Start Quiz

Discover the right content for your subjects

No need to cheat if you have everything you need to succeed! Packed into one app!

Study Plan

Be perfectly prepared on time with an individual plan.

Quizzes

Test your knowledge with gamified quizzes.

Flashcards

Create and find flashcards in record time.

Notes

Create beautiful notes faster than ever before.

Study Sets

Have all your study materials in one place.

Documents

Upload unlimited documents and save them online.

Study Analytics

Identify your study strength and weaknesses.

Weekly Goals

Set individual study goals and earn points reaching them.

Smart Reminders

Stop procrastinating with our study reminders.

Rewards

Earn points, unlock badges and level up while studying.

Magic Marker

Create flashcards in notes completely automatically.

Smart Formatting

Create the most beautiful study materials using our templates.

Sign up to highlight and take notes. It’s 100% free.

Get FREE ACCESS to all of our study material, tailor-made!

Over 10 million students from across the world are already learning smarter.

Get Started for Free
Illustration