Esters are a class of chemical compounds and functional groups. An alkyl is a Univalent radical consisting of Carbon and Hydrogen atoms arranged in a chain In the context of organic molecules aryl refers to any Functional group or Substituent derived from a Simple aromatic ring, may it be Phenyl A chemical compound is a substance consisting of two or more different elements chemically bonded together in a fixed proportion by Mass. In Organic chemistry, functional groups are specific groups of Atoms within Molecules that are responsible for the characteristic Chemical reactions Esters consist of an inorganic or organic acid in which at least one -OH (hydroxyl) group is replaced by an -O-alkyl (alkoxy) group. Inorganic chemistry is the branch of Chemistry concerned with the properties and behavior of Inorganic compounds This field covers all Chemical compounds Organic chemistry is a discipline within Chemistry which involves the scientific study of the structure properties composition reactions, and preparation In Computer science, ACID ( Atomicity Consistency Isolation Durability) is a set of properties that guarantee that Database transactions are Hydroxyl in Chemistry stands for a molecule consisting of an Oxygen atom and a Hydrogen atom connected by a Covalent bond. An alkyl is a Univalent radical consisting of Carbon and Hydrogen atoms arranged in a chain In Chemistry, the alkoxyl group is an Alkyl (carbon and hydrogen chain group linked to Oxygen thus R-O Some acids that are commonly esterified are carboxylic acids, phosphoric acid, sulfuric acid, nitric acid, and boric acid. Carboxylic acids are Organic acids characterized by the presence of a Carboxyl group, which has the formula -C(=OOH usually written -COOH or -CO2H Phosphoric acid, also known as orthophosphoric acid or phosphoric(V acid, is a mineral (inorganic acid having the Chemical formula Sulfuric (or sulphuric acid, H 2 S[[oxygen O]]4 is a strong Mineral acid. Nitric acid ( H[[nitrate NO3]] also known as Aqua fortis and spirit of nitre, is a highly corrosive and Boric acid, also called boracic acid or orthoboric acid or Acidum Boricum, is a mild Acid often used as an Antiseptic, Insecticide Volatile esters, particularly carboxylate esters, often have a pleasant smell and are found in perfumes, essential oils, and pheromones, and give many fruits their scent. Perfume is a mixture of fragrant Essential oils and Aroma compounds Fixatives and Solvents used to give the human body animals objects and living An essential oil is a concentrated Hydrophobic Liquid containing volatile Aroma compounds from Plants They are also known as volatile A pheromone (from Greek φέρω phero "to bear" + ‘ορμόνη " Hormone " is a Chemical that triggers a natural The term fruit has different meanings dependent on context and the term is not synonymous in Food preparation and Biology. Ethyl acetate and methyl acetate are important solvents; fatty acid esters form fat and lipids; phosphoesters form the backbone of DNA molecules; and polyesters are important plastics. Ethyl acetate ( systematically, ethyl ethanoate commonly abbreviated EtOAc or EA is the Organic compound with the formula CH3COOCH2CH3 Methyl acetate, also known as acetic acid methyl ester or methyl ethanoate, is a clear flammable liquid with a characteristic not unpleasant smell like certain A solvent is a liquid or gas that dissolves a solid liquid or gaseous Solute, resulting in a Solution. In Chemistry, especially Biochemistry, a fatty acid is a Carboxylic acid often with a long unbranched Aliphatic tail ( chain) which Fats consist of a wide group of compounds that are generally soluble in organic solvents and largely insoluble in water Lipids are broadly defined as any fat- Soluble ( lipophilic) naturally-occurring Molecule, such as fats oils waxes cholesterol sterols fat-soluble A phosphodiester bond is a group of strong covalent bonds between the phosphorus atom in a Phosphate group and two other Molecules over two Deoxyribonucleic acid ( DNA) is a Nucleic acid that contains the genetic instructions used in the development and functioning of all known Polyester is a category of Polymers which contain the Ester Functional group in their main chain Plastic is the general common term for a wide range of synthetic or semisynthetic organic solid materials suitable for the manufacture of industrial products Cyclic esters are called lactones. lactone is a cyclic Ester in Organic chemistry. It is the condensation product of an Alcohol group and a Carboxylic acid The name "ester" is derived from the German Essig-Äther (literally: vinegar ether), an old name for ethyl acetate. Ether is a class of Organic compounds which contain an ether group — an Oxygen Atom connected to two (substituted Alkyl Esters can be synthesized in a condensation reaction between an acid and an alcohol in a reaction known as esterification. In Chemistry, chemical synthesis is purposeful execution of Chemical reactions in order to get a product, or several products A condensation reaction is a Chemical reaction in which two Molecules or moieties ( Functional groups) combine to form one single molecule together with In Chemistry, an alcohol is any Organic compound in which a Hydroxyl group ( - O[[hydrogen H]]) is bound to a Carbon Esterification is the general name for a Chemical reaction in which two reactants (typically an alcohol and an acid form an Ester as the reaction product
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Nomenclature
An ester is named according to the two parts that make it up: the part from the alcohol and the part from the acid (in that order), for example ethyl ethanoate (see image below).
Since most esters, or carbonate, are derived from carboxylic acids, a specific nomenclature is used for them. For esters derived from the simplest carboxylic acids, the traditional name for the acid constituent is generally retained, e. g. , formate, acetate, propionate, butyrate. [1] For esters from more complex carboxylic acids, the systematic name for the acid is used, followed by the suffix -oate. For example, methyl formate is the ester of methanol and methanoic acid (formic acid): the simplest ester. Methyl formate, also called methyl methanoate, is the methyl Ester of Formic acid. Methanol, also known as methyl alcohol, carbinol, wood alcohol, wood naphtha or wood spirits, is a Chemical compound Formic acid (systematically called methanoic acid) is the simplest Carboxylic acid. It could also be called methyl methanoate. [2]
Esters of aromatic acids are also encountered, including benzoates such as methyl benzoate, and phthalates, with substitution allowed in the name. Benzoic acid, C7H6O2 (or C6H5COOH is a colorless crystalline solid and the simplest Aromatic Carboxylic acid Methyl benzoate is an Ester with the Chemical formula C6H5COOCH3 Phthalates, or phthalate esters, are esters of Phthalic acid and are mainly used as Plasticizers (substances added to Plastics to increase their
Physical properties
Esters participate in hydrogen bonds as hydrogen-bond acceptors, but cannot act as hydrogen-bond donors, unlike their parent alcohols. A hydrogen bond results from a Dipole-dipole force between an Electronegative atom and a Hydrogen atom bonded to Nitrogen, Oxygen This ability to participate in hydrogen bonding makes them more water-soluble than their parent hydrocarbons. Water is a common Chemical substance that is essential for the survival of all known forms of Life. Solubility is the characteristic Physical property referring to the ability of a given substance the Solute, to dissolve in a Solvent. In Organic chemistry, a hydrocarbon is an Organic compound consisting entirely of Hydrogen and Carbon. However, the limitations on their hydrogen bonding also make them more hydrophobic than either their parent alcohols or their parent acids. Their lack of hydrogen-bond-donating ability means that ester molecules cannot hydrogen-bond to each other, which, in general, makes esters more volatile than a carboxylic acid of similar molecular weight. In Chemistry, a molecule is defined as a sufficiently stable electrically neutral group of at least two Atoms in a definite arrangement held together by Carboxylic acids are Organic acids characterized by the presence of a Carboxyl group, which has the formula -C(=OOH usually written -COOH or -CO2H This property makes them very useful in organic analytical chemistry: Unknown organic acids with low volatility can often be esterified into a volatile ester, which can then be analyzed using gas chromatography, gas liquid chromatography, or mass spectrometry. Gas-liquid chromatography (GLC, or simply gas chromatography (GC, is a type of Chromatography in which the mobile phase is a carrier gas usually an Inert Gas-liquid chromatography (GLC, or simply gas chromatography (GC, is a type of Chromatography in which the mobile phase is a carrier gas usually an Inert Mass spectrometry is an analytical technique that identifies the chemical composition of a compound or sample based on the Mass-to-charge ratio of charged particles Many esters have distinctive odors, which has led to their use as artificial flavorings and fragrances. For example:
Ester synthesis
"Esterification" (condensation of an alcohol and an acid) is not the only way to synthesize an ester. Pineapple ( Ananas comosus) is the common name for an edible Tropical Plant and also its Fruit It is native to the southern part of Brazil Benzyl acetate is an Organic compound with the molecular formula C9H10O2 A pear is a pomaceous Fruit produced by a tree of Genus Pyrus. Garden strawberries are a common variety of strawberry cultivated worldwide Jasmine or Jessamine ( Jasminum) (from Persian yasmin, ie "gift from God" via Arabic) is a Genus of Shrubs This article is about the tree For other uses of the term "pine" see Pine (disambiguation. Butyl butyrate, or butyl butanoate is an Organic compound which is an Ester formed by the condensation of Butyric acid and Butanol. Pineapple ( Ananas comosus) is the common name for an edible Tropical Plant and also its Fruit It is native to the southern part of Brazil Ethyl acetate ( systematically, ethyl ethanoate commonly abbreviated EtOAc or EA is the Organic compound with the formula CH3COOCH2CH3 Nail polish or nail varnish is a Lacquer that is applied to the nails of both the Fingers and Toes usually cosmetically but also as A scale model is a representation or copy of an object that is larger or smaller than the actual size of the object. Paint is any Liquid, liquifiable or mastic composition which after application to a substrate in a thin layer is converted to an opaque Solid Model aircraft are flying or non-flying models of existing or imaginary Aircraft, often scaled down versions of full size planes using materials such as balsa Glue or adhesive is a compound that adheres or bonds two items together Ethyl butyrate, also known as ethyl butanoate, or butyric ether, is an Ester with the chemical formula CH3CH2CH2COOCH2CH3 For the fruit see Banana. For other meanings see Banana (disambiguation. Pineapple ( Ananas comosus) is the common name for an edible Tropical Plant and also its Fruit It is native to the southern part of Brazil Garden strawberries are a common variety of strawberry cultivated worldwide Pineapple ( Ananas comosus) is the common name for an edible Tropical Plant and also its Fruit It is native to the southern part of Brazil Ethyl cinnamate is the Ester of Cinnamic acid and Ethanol. It is present in the essential oil of Cinnamon; pure ethyl cinnamate has a "fruity Cinnamon ( Cinnamomum verum, synonym C zeylanicum) is a small Evergreen Tree 10–15 metres (32 Ethyl formate is an Ester formed when Ethanol reacts with Formic acid. The lemon ( Citrus × limon) is a hybrid in cultivated wild plants Rum is a Distilled beverage made from Sugarcane by-products such as Molasses and sugarcane Juice by a process of fermentation Garden strawberries are a common variety of strawberry cultivated worldwide Ethyl heptanoate is the Ester resulting from the condensation of Heptanoic acid and Ethanol. The Apricot ( Prunus armeniaca, "Armenian plum" in Latin syn This article is about the Cherry berry also classified as fruit for the ornamental tree See Cherry Blossom. For the Tokyo University supercomputer see Gravity Pipe. GRAPE, or GRA phics P rogramming E nvironment is The raspberry (plural raspberries) is the edible Fruit of a multitude of plant species in the subgenus Idaeobatus of the genus Rubus The apple is the pomaceous Fruit of the apple tree Species Malus domestica in the Rose family Rosaceae. Ethyl lactate, also known as lactic acid ethyl ester is a monobasic Ester formed from Lactic acid and Ethanol, commonly used as a Solvent Butter is a Dairy product made by churning fresh or fermented Cream or Milk. For the 1993 hip-hop single by the Wu-Tang Clan see CREAM CREAM is an acronym for Cognitive Reliability Error Analysis Method a For the Tokyo University supercomputer see Gravity Pipe. GRAPE, or GRA phics P rogramming E nvironment is Ethyl pentanoate, also commonly known as ethyl valerate is an Organic compound used in flavors The apple is the pomaceous Fruit of the apple tree Species Malus domestica in the Rose family Rosaceae. Geranyl acetate is a natural Organic compound that is classified as a monoterpene. Gardeners often use the name "geranium" to mean Pelargonium: see below. This article is about the Cherry berry also classified as fruit for the ornamental tree See Cherry Blossom. The apple is the pomaceous Fruit of the apple tree Species Malus domestica in the Rose family Rosaceae. The Chemical compound isobutyl acetate, with systematic name 2-methylpropyl ethanoate, is a common solvent This article is about the Cherry berry also classified as fruit for the ornamental tree See Cherry Blossom. The raspberry (plural raspberries) is the edible Fruit of a multitude of plant species in the subgenus Idaeobatus of the genus Rubus Garden strawberries are a common variety of strawberry cultivated worldwide The raspberry (plural raspberries) is the edible Fruit of a multitude of plant species in the subgenus Idaeobatus of the genus Rubus Refractive index | --> Isoamyl acetate, also known as isopentyl acetate, is an Organic compound that is the Ester formed from Isoamyl A pear is a pomaceous Fruit produced by a tree of Genus Pyrus. For the fruit see Banana. For other meanings see Banana (disambiguation. A pear drop is a boiled sweet made from Sugar and Flavourings. Isopropyl acetate is an Ester, an Organic compound which is the product of condensation of Acetic acid and Isopropanol. The Lavenders Lavandula are a Genus of about 25–30 species of Flowering plants in the mint family Lamiaceae, native to the Mediterranean Common sage ( Salvia officinalis) is a small perennial Evergreen Subshrub, with woody stems grayish leaves and blue to purplish flowers The peach ( Prunus persica) is a species of Prunus native to China that bears an edible juicy fruit also called a peach The apple is the pomaceous Fruit of the apple tree Species Malus domestica in the Rose family Rosaceae. The peach ( Prunus persica) is a species of Prunus native to China that bears an edible juicy fruit also called a peach Methyl acetate, also known as acetic acid methyl ester or methyl ethanoate, is a clear flammable liquid with a characteristic not unpleasant smell like certain Peppermint ( Mentha × piperita) is a hybrid mint, a cross between Watermint ( Mentha aquatica) and Spearmint Methyl anthranilate, also known as MA, methyl 2-aminobenzoate or carbomethoxyaniline, is an Ester of Anthranilic acid. For the Tokyo University supercomputer see Gravity Pipe. GRAPE, or GRA phics P rogramming E nvironment is Jasmine or Jessamine ( Jasminum) (from Persian yasmin, ie "gift from God" via Arabic) is a Genus of Shrubs Methyl benzoate is an Ester with the Chemical formula C6H5COOCH3 Ylang-ylang (ˈiːlæŋˈʔiːlæŋ (ee-lang ee-lang Cananga odorata, is a small flower of the Cananga tree The Feijoa ( Feijoa sellowiana, synonym Acca sellowiana) also known as Pineapple Guava or Guavasteen, is an Evergreen This article is about the Cherry berry also classified as fruit for the ornamental tree See Cherry Blossom. Methyl butyrate, also known under the systematic name methyl butanoate, is the Methyl Ester of Butyric acid. Pineapple ( Ananas comosus) is the common name for an edible Tropical Plant and also its Fruit It is native to the southern part of Brazil The apple is the pomaceous Fruit of the apple tree Species Malus domestica in the Rose family Rosaceae. Methyl cinnamate is the Methyl Ester of Cinnamic acid. It is found naturally in a variety of plants including in fruits like Strawberry Garden strawberries are a common variety of strawberry cultivated worldwide Methyl pentanoate, commonly known as methyl valerate, is the Methyl Ester of Pentanoic acid (valeric acid with a fruity Odor A flower, also known as a bloom or Blossom, is the reproductive structure found in Flowering plants (plants of the division Magnoliophyta, also Refractive index | --> Methyl phenylacetate is an Organic compound that is the Ester formed from Methanol and Phenylacetic acid Honey is a sweet and Viscous fluid produced by Honey bees (and some other species and derived from the nectar of Flowers According to the Methyl salicylate ( Chemical formula C6H4(HOCOOCH3 also known as salicylic acid methyl ester, oil of wintergreen, Methyl salicylate ( Chemical formula C6H4(HOCOOCH3 also known as salicylic acid methyl ester, oil of wintergreen, Root beer, also known as Sarsaparilla, is a carbonated Beverage originally created from Sassafras. Wintergreen is a group of plants Wintergreen once commonly referred to Plants that continue Photosynthesis (remain Green) throughout the Winter Germolene is a brand name used on a range of Antiseptic products produced by the company Bayer. Raljex Spray is a spray specifically used for soothing painful Muscles and joints in humans not animals An orange —specifically the sweet orange —is the Citrus fruit Citrus sinensis ( syn Octyl acetate, or octyl ethanoate is an Ester that is formed from Octanol (octyl alcohol and Acetic acid. An orange —specifically the sweet orange —is the Citrus fruit Citrus sinensis ( syn Butyric acid (from Greek βούτυρος = butter) also known under the systematic name butanoic acid, is a Carboxylic acid with the structural The parsnip ( Pastinaca sativa) is a Root vegetable related to the Carrot. Amyl acetate (also pentyl ethanoate, pentyl acetate) is an Organic compound and an Ester with the chemical formula CH3COO(CH24CH3 The apple is the pomaceous Fruit of the apple tree Species Malus domestica in the Rose family Rosaceae. For the fruit see Banana. For other meanings see Banana (disambiguation. Pentyl butyrate, also known as pentyl butanoate or amyl butyrate, is an Ester that is formed when Pentanol is reacted with Butyric The Apricot ( Prunus armeniaca, "Armenian plum" in Latin syn A pear is a pomaceous Fruit produced by a tree of Genus Pyrus. Pineapple ( Ananas comosus) is the common name for an edible Tropical Plant and also its Fruit It is native to the southern part of Brazil The apple is the pomaceous Fruit of the apple tree Species Malus domestica in the Rose family Rosaceae. Pineapple ( Ananas comosus) is the common name for an edible Tropical Plant and also its Fruit It is native to the southern part of Brazil Pentyl pentanoate (C4H9COOC5H11 is an Ester used in dilute solution to replicate the scent or flavour of Apple, The apple is the pomaceous Fruit of the apple tree Species Malus domestica in the Rose family Rosaceae. The Chemical compound propyl acetate, also known as propyl ethanoate, is a common Solvent. A pear is a pomaceous Fruit produced by a tree of Genus Pyrus. Rum is a Distilled beverage made from Sugarcane by-products such as Molasses and sugarcane Juice by a process of fermentation This article is about the Cherry berry also classified as fruit for the ornamental tree See Cherry Blossom. Esters can be prepared in the laboratory in a number of other ways:
- Transesterifications between other esters
- Dieckmann condensation or Claisen condensation of esters carrying acidic α-protons
- Favorskii rearrangement of α-haloketones in presence of base
- Nucleophilic displacement of alkyl halides with carboxylic acid salts
- Nucleophilic displacement of acyl halides with alcohols
- Baeyer-Villiger oxidation of ketones with peroxides
- Pinner reaction of nitriles with an alcohol
Ester reactions
Esters react in a number of ways:
- Esters may undergo hydrolysis - the breakdown of an ester by water. In Organic chemistry, transesterification is the process of exchanging the Alcohol group of an Ester compound with another Alcohol. The Dieckmann condensation is the Intramolecular Chemical reaction of di Esters with base to give β-ketoesters The Claisen condensation (not to be confused with the Claisen rearrangement) is a Carbon-carbon bond forming reaction that occurs between two Esters The Favorskii rearrangement (not to be confused with the Favorskii reaction) named for the Russian chemist Alexei Yevgrafovich Favorskii, In organic and Inorganic chemistry, nucleophilic substitution is a fundamental class of Substitution reaction in which an "electron rich" The haloalkanes (also known as halogenoalkanes or alkyl halides) are a group of Chemical compounds consisting of Alkanes such as Methane In organic and Inorganic chemistry, nucleophilic substitution is a fundamental class of Substitution reaction in which an "electron rich" An acyl halide (also known as an acid halide) is a Chemical compound derived from an Oxoacid by replacing a Hydroxyl group with a In Chemistry, an alcohol is any Organic compound in which a Hydroxyl group ( - O[[hydrogen H]]) is bound to a Carbon The Baeyer-Villiger oxidation is an Organic reaction in which a Ketone is oxidized to an Ester by treatment with Peroxy acids or The Pinner reaction (after Adolf Pinner) is an Organic reaction of a Nitrile with an Alcohol under Acid Catalysis for instance A nitrile is any Organic compound which has a - C ≡ N Functional group. Hydrolysis is a Chemical reaction during which one or more water molecules are split into hydrogen and hydroxide ions which may go on to participate in further reactions This process can be catalyzed both by acids and bases. The base-catalyzed process is called saponification. Saponification is the Hydrolysis of an Ester under basic conditions to form an Alcohol and the Salt of a Carboxylic acid The hydrolysis yields an alcohol and a carboxylic acid or its carboxylate salt. Carboxylic acids are Organic acids characterized by the presence of a Carboxyl group, which has the formula -C(=OOH usually written -COOH or -CO2H A carboxylate anion is an Ion with Negative charge that contains the group -COO&minus Salt is a Dietary mineral composed primarily of Sodium chloride that is essential for Animal life but toxic to most land plants
- Esters also react if heated with primary or secondary amines, producing amides. Amines are Organic compounds and Functional groups that contain a basic Nitrogen Atom with a Lone pair. In Chemistry, an amide is one of three kinds of Compounds (sometimes called acid amide the organic Functional group characterized
- Phenyl esters react to hydroxyarylketones in the Fries rearrangement. The Fries rearrangement, named for the German chemist Karl Theophil Fries, is a Rearrangement reaction of a Phenyl Ester to a Hydroxy
- Di-esters such as diethyl malonate react as nucleophile with alkyl halides in the malonic ester synthesis after deprotonation. Diethyl malonate, also known as DEM, is the Diethyl Ester of Malonic acid. In Chemistry, a nucleophile (literally nucleus lover as in nucleus and phile) is a Reagent that forms a Chemical bond to The haloalkanes (also known as halogenoalkanes or alkyl halides) are a group of Chemical compounds consisting of Alkanes such as Methane The malonic ester synthesis is a Chemical reaction where Diethyl malonate or another Ester of Malonic acid is Alkylated at the carbon Deprotonation is a Chemistry term that refers to the removal of a Proton ( Hydrogen Cation H+ from a Molecule, forming
- Specific esters are functionalized with an α-hydroxyl group in the Chan rearrangement. The Chan rearrangement is a Chemical reaction that involves rearranging an Acyloxy Acetate ( 1) in the presence of a strong base
- Esters are converted to isocyanates through intermediate hydroxamic acids in the Lossen rearrangement. Isocyanate is the Functional group of atoms &ndashN=C=O (1 Nitrogen, 1 Carbon, 1 Oxygen) not to be confused with the Cyanate A hydroxamic acid is a class of Chemical compounds sharing the same Functional group in which an Amine is inserted into an Carboxylic acid. The Lossen rearrangement is the Chemical reaction of a Hydroxamic acid 1 with a dehydration agent (such as Tosyl chloride) to form the O-derivative
- Esters with β-hydrogen atoms can be converted to alkenes in ester pyrolysis. Ester pyrolysis in Organic chemistry is a Vacuum pyrolysis reaction converting Esters containing a β-hydrogen atom into the corresponding Carboxylic
External links
- An introduction to esters
- Molecule of the month: Ethyl acetate and other esters
- Making an Ester A simple guide to naming and making esters, as well as the chemistry behind it.
References
Dictionary
ester
-noun
- (organic chemistry) A compound most often formed by the condensation of an alcohol and an acid, with elimination of water. It contains the functional group carbon-oxygen double bond joined via carbon to another oxygen atom.
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