General formula of an ester of a carboxylic acid.

In chemistry, esters are organic compounds in which an organic group (symbolised by R' in this article) replaces a hydrogen atom (or more than one) in an oxygen acid. An oxygen acid is an acid whose molecule has an -OH group from which the hydrogen (H) can dissociate as an H⁺ ion. This is the general displayed formular of an ester File links The following pages link to this file: Alkyl User:Borb Categories: GFDL images ... // Introduction The fundamental component of chemistry is that it involves matter in some way (this explains its broad reach). ... An organic compound is any member of a large class of chemical compounds whose molecules contain carbon, with the exception of carbides, carbonates, carbon oxides and gases containing carbon. ... An alkane in organic chemistry is a type of hydrocarbon in which the molecule has the maximum possible number of hydrogen atoms and so has no double bonds (they are saturated). ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... Properties An atom (Greek άτομον from ά: non and τομον: divisible) is a submicroscopic structure found in all ordinary matter. ... General Name, Symbol, Number oxygen, O, 8 Chemical series Chalcogens Group, Period, Block 16, 2, p Appearance colorless Atomic mass 15. ... An acid (from Arabic Azait meaning oil, often represented by the generic formula AH) is typically a water-soluble, sour-tasting chemical compound. ... A molecule is the smallest particle of a pure chemical substance that still retains its chemical composition and properties. ... Hydroxide is a polyatomic ion consisting of oxygen and hydrogen: −O−H It has a charge of −1. ... In ecology functional groups are collections of organisms based on morphological, physiological, behavioral, biochemical, or environmental responses or on trophic criteria. ... Dissociation is a psychological state or condition in which certain thoughts, emotions, sensations, or memories are separated from the rest of the psyche. ... An ion is an atom or group of atoms with a net electric charge. ...

The most common esters are the carboxylate esters, where the acid in question is a carboxylic acid. For example, if the acid is acetic acid, the ester is called an acetate. Esters may also be formed with inorganic acids; for example, dimethyl sulfate is an ester, and sometimes called "sulfuric acid, dimethyl ester". Structure of a carboxylic acid Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)-OH, usually written as COOH. In general, the salts and anions of carboxylic acids are called carboxylates. ... Flash point 43 Â°C R-phrases , S-phrases , , , US Permissible exposure limit (PEL) 10 ppm Supplementary data page Structure & properties n, εr, etc. ... Acetate, or ethanoate, is the anion of a salt or ester of acetic acid. ... Inorganic chemistry is the branch of chemistry concerned with the properties and reactions of inorganic compounds. ... Dimethyl sulfate has chemical formula (CH3)2SO4. ... Sulfuric acid (British English: sulphuric acid), H2SO4, is a strong mineral acid. ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ...

Esters are named similarly to salts; although they don't really have cations and anions, the terminology follows the same pattern: a more electropositive part followed by a more electronegative part. Salt Crystals (http://www. ... A cation is an ion with positive charge. ... An anion is an ion with negative charge. ...

An ester can be thought of as a product of a condensation reaction of an acid (usually an organic acid) and an alcohol (or phenol compound), although there are other ways to form esters. Condensation is a type of chemical reaction in which two molecules with -OH groups are joined with eliminating a water molecule from their -OH groups. A condensation reaction to form an ester is called esterification. Esterification can be catalysed by the presence of H⁺ ions. Sulfuric acid is often used as a catalyst for this reaction. The name ester is derived from the German Essig-Äther, an old name for acetic acid ethyl ester (ethyl acetate). A condensation reaction (also known as a dehydration reaction or dehydration synthesis when water is lost) is a chemical reaction in which two molecules or moieties react and become covalently bonded to one another by the concurrent loss of a small molecule, often water or methanol. ... An organic acid is an organic compound that is an acid. ... In general usage, alcohol (from Arabic al-kukhul الكحول, al meaning the and kukhul meaning spirit, the chemical) refers almost always to ethanol, also known as grain alcohol, and often to any beverage that contains ethanol (see alcoholic beverage). ... In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of a hydroxyl group (-OH) attached to an aromatic hydrocarbon group. ... A chemical reaction is a process that results in the interconversion of Chemical substances . ... A molecule is the smallest particle of a pure chemical substance that still retains its chemical composition and properties. ... Water has the chemical formula H2O, meaning that one molecule of water is composed of two hydrogen atoms and one oxygen atom. ... Esterification is the general name for a chemical reaction in which two chemicals (typically an alcohol and an acid) form an ester as the reaction product. ... A catalyst (Greek: καταλύτης, catalytÄ“s) is a substance that accelerates the rate (speed) of a chemical reaction (see also catalysis). ... Ethyl acetate, also known as acetic acid ethyl ester, ethyl ethanoate, or acetic ester, is a clear, flammable liquid with a characteristic, not unpleasant smell like certain glues or nail polish removers. ...

Naming of esters

Ethyl acetate structure

Esters can be produced by an equilibrium reaction between an alcohol and a carboxylic acid. The ester is named according to the alkyl group (the part from the alcohol) and then the alkanoate (the part from the carboxylic acid) which make it up.^[1] For example, the reaction between methanol and butyric acid yields the ester methyl butyrate C₃H₇-COO-CH₃ (as well as water). The simplest ester is H-COO-CH₃ (methyl formate, also called methyl methanoate). Image File history File links Ethylethanoate. ... Chemical equilibrium is the state in which a chemical reaction proceeds at the same rate as its reverse reaction; the rates of the forward and reverse reactions are equal, and the concentration of the reactants and products stop changing. ... In general usage, alcohol (from Arabic al-kukhul الكحول, al meaning the and kukhul meaning spirit, the chemical) refers almost always to ethanol, also known as grain alcohol, and often to any beverage that contains ethanol (see alcoholic beverage). ... Structure of a carboxylic acid Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)-OH, usually written as COOH. In general, the salts and anions of carboxylic acids are called carboxylates. ... An Alkyl is a univalent radical containing only carbon and hydrogen atoms arranged in a chain. ... In general usage, alcohol (from Arabic al-kukhul الكحول, al meaning the and kukhul meaning spirit, the chemical) refers almost always to ethanol, also known as grain alcohol, and often to any beverage that contains ethanol (see alcoholic beverage). ... Structure of a carboxylic acid Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)-OH, usually written as COOH. In general, the salts and anions of carboxylic acids are called carboxylates. ... Methanol, also known as methyl alcohol or wood alcohol, is a chemical compound with chemical formula CH3OH. It is the simplest alcohol, and is a light, volatile, colourless, tasteless, flammable, poisonous liquid with a very faint odor. ... Butyric acid, IUPAC name n-Butanoic acid, or normal butyric acid, is a carboxylic acid with structural formula CH3CH2CH2-COOH. It is notably found in rancid butter, parmesan cheese, or vomit and has an unpleasant odor and acrid taste, with a sweetish aftertaste (similar to ether). ... Methyl butyrate is an ester with a fruity fragrance resembling apples or pineapples. ... Methyl formate, also called methyl methanoate, is the methyl ester of formic acid. ...

For esters derived from the simplest carboxylic acids, the traditional names names are recommended by IUPAC,^[2] viz, formate, acetate, propionate, butyrate, though out of these only acetate may carry further substituents. For esters from higher acids, the alkane name with an -oate ending is generally preferred, e.g., hexanoate. Common esters of aromatic acids include benzoates such as methyl benzoate, and phthalates, with substitution allowed in the name. Structural formula Benzoic acid, C6H5C(O)OH, is an aromatic carboxylic acid. ... benzoic acid, replace the hydrogen atom of the alcohol group with a methyl group, process can be used for ethyl benzoate, propyl benzoate, and also using other carboxylate ions ... R,R=CnH2n+1; n=4-15 Phthalates are a group of chemical compounds that are mainly used as plasticizers -- substances added to plastics to increase their flexibility. ...

Physical properties

Esters participate in hydrogen bonds as hydrogen-bond acceptors, but cannot act as hydrogen-bond donors, unlike their parent alcohols. This ability to participate in hydrogen bonding makes them more water-soluble than their parent hydrocarbons. However, the limitations on their hydrogen bonding also make them more hydrophobic than either their parent alcohols or parent acids. Their lack of hydrogen-bond-donating ability means that ester molecules cannot hydrogen-bond to each other, which makes esters generally more volatile than an carboxylic acid of similar molecular weight. 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 analysed using gas chromatography, gas liquid chromatography, or mass spectrometry. Many esters have distinctive odors, which has led to their widespread use as artificial flavorings and fragrances. For example: Hydrogen bonds between water molecules are diagramatically represented by the black lines. ... Water (from the Old English word wæter; c. ... It has been suggested that this article or section be merged with Solution. ... Hydrocarbons are refined at oil refineries and chemical plants In chemistry, a hydrocarbon is any chemical compound that consists only of the elements carbon (C) and hydrogen (H). ... A molecule is the smallest particle of a pure chemical substance that still retains its chemical composition and properties. ... Structure of a carboxylic acid Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)-OH, usually written as COOH. In general, the salts and anions of carboxylic acids are called carboxylates. ... 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 such as helium or nitrogen, and the stationary phase is a microscopic layer of liquid on an inert solid support. ... ... Mass spectrometry is an analytical technique which determines the mass-to-charge (m/z) ratio of ions. ...

methyl butyrate smells of pineapple or apple

methyl salicylate (oil of wintergreen) smells of the ointments called Germolene™ and Ralgex™ in the UK

methyl benzoate smells of fruity-ylang ylang

ethyl formate smells of rum

ethyl butyrate smells of pineapple or strawberry

ethyl salicylate smells of oil of wintergreen

ethyl heptanoate smells of grape

propyl isobutyrate (rum)

isobutyl formate (raspberries)

butyl butyrate (pineapple)

pentyl acetate smells of banana

pentyl pentanoate smells of apple

pentyl butyrate smells of pear or apricot

isopentyl acetate smells of pear or banana (it is used as the flavouring in the manufacturing of old fashioned Pear Drops)

octyl acetate smells of fruity-orange

benzyl acetate smells slightly of jasmine

Methyl butyrate is an ester with a fruity fragrance resembling apples or pineapples. ... Binomial name Ananas comosus (L.) Merr. ... Binomial name Malus domestica Borkh. ... Chemical structure of methyl salicylate Methyl salicylate (chemical formula C6H4(HO)COOCH3; also known as salicylic acid methyl ester, oil of wintergreen, betula oil, methyl ester) is a natural product of many species of plants. ... Methyl salicylate (chemical formula C6H4(HO)COOCH3; also known as oil of wintergreen, betula oil, methyl ester) is a natural product of many species of plants. ... benzoic acid, replace the hydrogen atom of the alcohol group with a methyl group, process can be used for ethyl benzoate, propyl benzoate, and also using other carboxylate ions ... Binomial nomenclature Cananga odorata Ylang-ylang is the flower of the cananga tree. ... Ethyl formate, also known as ethyl methanoate is an ester formed when ethanol reacts with formic acid. ... Caribbean rum, circa 1941 Rum is a distilled beverage made from sugarcane by-products such as molasses and sugarcane juice by a process of fermentation and distillation. ... Chemical structure of ethyl butyrate Ethyl butyrate, also known as ethyl butanoate is an ester with the chemical formula CH3CH2CH2COO-CH2CH3, with one oxygen having a double bond. ... Binomial name Ananas comosus (L.) Merr. ... Species See text The strawberry (Fragaria) is a genus of plants in the family Rosaceae, and the fruit of these plants. ... Ethyl salicylate is the ester formed by the condensation of salicylic acid and ethanol. ... Methyl salicylate (chemical formula C6H4(HO)COOCH3; also known as oil of wintergreen, betula oil, methyl ester) is a natural product of many species of plants. ... Ethyl heptanoate is the ester resulting from the condensation of heptanoic acid and ethanol. ... To meet Wikipedias quality standards, this article or section may require cleanup. ... Pentyl acetate is an organic ester. ... Species Hybrid origin; see text A banana plant is a herb in the genus Musa, which because of its size and structure, is often mistaken for a tree. ... Pentyl pentanoate is an ester used in dilute quantities to replicate the scent or flavour of apple, and sometimes pineapple. ... Binomial name Malus domestica Borkh. ... Pentyl butyrate, also known as Pentyl butanoate, is an ester that is formed when pentanol is reacted with butyric acid, usually in the presence of sulfuric acid as a catalyst. ... Species About 30 species, including: Pyrus amygdaliformis Pyrus austriaca Pyrus balansae Pyrus betulifolia Pyrus bourgaeana Pyrus bretschneideri Pyrus calleryana Pyrus caucasica Pyrus communis Pyrus cordata Pyrus cossonii Pyrus elaeagrifolia Pyrus fauriei Pyrus kawakamii Pyrus korshinskyi Pyrus lindleyi Pyrus nivalis Pyrus pashia Pyrus persica Pyrus phaeocarpa Pyrus pyraster Pyrus pyrifolia Pyrus... Binomial name Prunus armeniaca L. The Apricot (Prunus armeniaca, syn. ... Species About 30 species, including: Pyrus amygdaliformis Pyrus austriaca Pyrus balansae Pyrus betulifolia Pyrus bourgaeana Pyrus bretschneideri Pyrus calleryana Pyrus caucasica Pyrus communis Pyrus cordata Pyrus cossonii Pyrus elaeagrifolia Pyrus fauriei Pyrus kawakamii Pyrus korshinskyi Pyrus lindleyi Pyrus nivalis Pyrus pashia Pyrus persica Pyrus phaeocarpa Pyrus pyraster Pyrus pyrifolia Pyrus... Species Hybrid origin; see text A banana plant is a herb in the genus Musa, which because of its size and structure, is often mistaken for a tree. ... Orange—specifically, sweet orange—refers to the citrus tree Citrus sinensis and its fruit. ... Benzyl acetate Benzyl acetate is an organic compound with the molecular formula C9H10O2. ... Species About 200 species, including: Jasminum angulare Jasminum azoricum Jasminum beesianum Jasminum dichotomum - Gold Coast Jasmine Jasminum floridum Jasminum fluminense - African Jasmine Jasminum fruticans Jasminum humile - Yellow Jasmine Jasminum mesnyi - Primrose Jasmine Jasminum multiflorum - Star Jasmine Jasminum nitidum - Shining Jasmine Jasminum nudiflorum - Winter Jasmine Jasminum officinale - Common Jasmine Jasminum parkeri...

Reactions

Ester saponification (basic hydrolysis)

Esters may undergo hydrolysis - the breakdown of an ester by water. This process can be catalyzed both by acids and bases. The base-catalyzed process is called saponification. The hydrolysis yields an alcohol and a carboxylic acid or its carboxylate salt. Shortened length of Ester_Hydrolysis. ... Hydrolysis is a chemical process in which a molecule is cleaved into two parts by the addition of a molecule of water. ... Saponification is the hydrolysis of an ester under basic conditions to form an alcohol and the salt of the acid. ... Structure of a carboxylic acid Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)-OH, usually written as COOH. In general, the salts and anions of carboxylic acids are called carboxylates. ... Structure of a carboxylic acid Carboxylic acids, also known as alkanoic acids, are organic acids characterized by the presence of a carboxyl group and have the general chemical formula R-C(=O)-OH, also written as R-COOH, where R is a hydrogen or an alkyl group. ... Salt Crystals (http://www. ...

Esters also react if heated with primary or secondary amines, producing amides. Ammonia Amines are organic compounds containing nitrogen as the key atom in the amine functional group. ... In chemistry, the term amide has several meanings. ...

Phenyl esters react to hydroxyarylketones in the Fries rearrangement. The Fries rearrangement is a rearrangement reaction of a phenyl ester to a hydroxy aryl ketone by catalysis of lewis acids . // Mechanism Despite many efforts a definitive reaction mechanism for the Fries rearrangement is not available. ...

External links

• Molecule of the month: Ethyl acetate and other esters

References

1. ^  IUPAC naming of esters
2. ^  IUPAC parent groups using traditional names