All content on this website, including dictionary, thesaurus, literature, geography, and other reference data is for informational purposes only. Don't want to keep filling in name and email whenever you want to comment? Don’t forget to count the carbon atom in the carbonyl group when determining the number of carbon atoms in the chain. Esters are used in technology as plastic monomers (acrylates and vinyl acetates), plasticizers for plastics (dioctyl and dibutyl phthalates), detergents (alkyl sulfates), solvents (amyl, butyl, and ethyl acetates), extraction agents and pesticides (esters of phosphoric acid), explosives (esters of nitric acid and polyhydric alcohols, such as nitroglycerin), pharmaceuticals (validol and aspirin), and fragrances (benzyl acetate and terpenyl acetate). (d) An atomic model of ethyl butanoate. Usually concentrated sulfuric acid is used as a catalyst. The oxygen atom bonded to two different carbon atoms is located between the two sections. A new bond is formed between the oxygen atom of the hydroxyl group and the carbonyl carbon atom of the carboxylic acid. In some instances, they have a fruity or flowery fragrance. • Describe the conditions needed to produce esters. An ester is a carboxylic acid derivative. It is therefore an ester and has a $$-$$C$$=$$O (carbonyl) group as well as an oxygen atom bonded to the carbon atom of the carbonyl and another carbon atom. There is only one carbon atom in the left-hand chain (from the alcohol). Esters are usually obtained by esterification (see). Esters are hydrolyzed by the action of water to form the corresponding alcohol and acid, in accordance with the general formula. Figure $$\PageIndex{1}$$ shows models for two common esters. (If it were hydrogen atom, the compound would be a carboxylic acid.) For example, when ethanol and acetic acid react, ethyl acetate (an ester) … The $$-$$C$$=$$O (carbonyl) group is located at the first carbon atom of the carboxylic acid chain. Organizing and providing relevant educational content, resources and information for students. The nomenclature for the salts and esters is similar; for example, NaOCOCH3 is called sodium acetate, and C2H5OCOCH3 is known as ethyl acetate. Draw the structural and condensed structural representations for the organic compound ethyl hexanoate. Chemistry » Organic Molecules » IUPAC Naming And Formulae. $$\overset{\underset{\mathrm{def}}{}}{=}$$, $$\color{red}{\textbf{ethyl}}\color{orange}{\textbf{ butanoate}}$$, Determine which part is from the alcohol and which is from the carboxylic acid, Number the carbon atoms on the carbon chains, Combine the elements of the compound’s name into a single word in the order of chain from the alcohol; prefix (from chain containing carbonyl functional group), name ending according to functional group, Place the functional group as well as any branched groups, Combine this information and add the hydrogen atoms, $$\text{CH}_{3}\text{CH}_{2}\text{CH}_{2}\text{CH}_{2}\text{CH}_{2}\text{COO}$$, Physical Properties and Intermolecular Forces, Physical Properties and Functional Groups, Addition, Elimination and Substitution Reactions. This is therefore an ester and the suffix is -oate. The part containing the carbonyl group was formed from the carboxylic acid and is on the right here. This is a lesson from the tutorial, Organic Molecules and you are encouraged to log in or register, so that you can track your progress. For this tutorial, we will only be concerned with examples where the hydrogen atom has been replaced by an alkyl group (that is a group derived from the alkane series). An ester is a carboxylic acid derivative. 1. Of the other reactions in which esters display acylating properties, the most common are transesterification, alcoholysis, and double exchange reactions. The esterification process of ethanol and butanoic acid to ethyl butanoate and water. There are three carbon atoms in the right-hand chain (from the carboxylic acid) therefore the prefix will be propan-. This modified article is licensed under a CC BY-NC-SA 4.0 license. The (a) structural, (b) condensed structural and (c) molecular formula representations of ethyl butanoate. When an alcohol reacts with a carboxylic acid an ester is formed. Other esters—mainly those of the terpene alcohols—are components of essential oils. Register or login to make commenting easier. Carboxylic acid esters of low molecular weight are colourless, volatile liquids with pleasant odours, slightly soluble in water. The compound has the suffix -oate. Now condense the part that came from the alcohol, starting from the $$-\text{O}-$$: $$\text{CH}_{3}\text{CH}_{2}\text{CH}_{2}\text{CH}_{2}\text{CH}_{2}\text{COOCH}_{2}\text{CH}_{3}$$. The part containing the oxygen atom bonded to two different carbon atoms was formed from the alcohol and is on the left here. The reaction is catalyzed by acids and even more so by bases. The ethyl tells us that there are two carbon atoms in the part of the chain from the alcohol. Unless specified, this website is not in any way affiliated with any of the institutions featured. The compound formed by the elimination of water and the bonding of an alcohol and an organic acid. Therefore this will be methyl. The making of esters is also called esterification. Figure $$\PageIndex{1}$$: The Structure of Esters. The first O is for the $$-$$C$$=$$O, the second is from the $$-\text{O}-$$.