See Also

Ester

In chemistry Chemistry

Chemistry is the science [i] of matter [i] at the atom [i]ic to molecular [i] scale, dealing primarily ... 

, esters are organic compound Organic compound

An organic compound is any member of a large class of chemical compound [i]s whose molecule [i]s contain ... 

s in which an organic group Alkane

An alkane is an acyclic saturated [i] hydrocarbon [i]. ... 

  replaces a hydrogen Hydrogen

|- | Triple point [i] || 13.8033 K, 7.042 kPa ... 

 atom Atom

In chemistry [i] and physics [i], an atom is the smallest possible particle of a chemical element [i] t ... 

  in an oxygen Oxygen

Oxygen is a chemical element [i] with the chemical symbol O and atomic number [i] 8. ... 

 acid. An oxygen acid is an acid whose molecule Molecule

In chemistry, a molecule is an aggregate of two or more atom [i]s in a definite arrangement held togethe ... 

 has an - group Functional group

In organic chemistry [i] functional groups are specific groups of atom [i]s within molecule [i]s, that ... 

 from which the hydrogen can dissociate as an H+ ion. The most common esters are the carboxylate esters, where the acid in question is a carboxylic acid Carboxylic acid

Carboxylic acids are organic acid [i]s characterized by the presence of a carboxyl group, which ha ... 

. For example, if the acid is acetic acid Acetic acid

Acetic acid, also known as ethanoic acid, is an organic [i] chemical compound [i] ... 

, the ester is called an acetate. Esters may also be formed with inorganic acids; for example, dimethyl sulfate Dimethyl sulfate

Dimethyl sulfate is a chemical compound [i] with formula [i]22. ... 

 is an ester, and sometimes called "sulfuric acid Sulfuric acid

Sulfuric acid , H [i]2S [i]O [i]4, is a strong mineral acid [i]. ... 

, dimethyl ester".

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Encyclopedia


In chemistry Chemistry

Chemistry is the science [i] of matter [i] at the atom [i]ic to molecular [i] scale, dealing primarily ... 

, esters are organic compound Organic compound

An organic compound is any member of a large class of chemical compound [i]s whose molecule [i]s contain ... 

s in which an organic group Alkane

An alkane is an acyclic saturated [i] hydrocarbon [i]. ... 

  replaces a hydrogen Hydrogen

|-
| Triple point [i] || 13.8033 K, 7.042 kPa
... 

 atom Atom

In chemistry [i] and physics [i], an atom is the smallest possible particle of a chemical element [i] t ... 

  in an oxygen Oxygen

Oxygen is a chemical element [i] with the chemical symbol O and atomic number [i] 8.... 

 acid. An oxygen acid is an acid whose molecule Molecule

In chemistry, a molecule is an aggregate of two or more atom [i]s in a definite arrangement held togethe ... 

 has an - group Functional group

In organic chemistry [i] functional groups are specific groups of atom [i]s within molecule [i]s, that ... 

 from which the hydrogen can dissociate as an H+ ion.

The most common esters are the carboxylate esters, where the acid in question is a carboxylic acid Carboxylic acid

Carboxylic acids are organic acid [i]s characterized by the presence of a carboxyl group, which ha ... 

. For example, if the acid is acetic acid Acetic acid

Acetic acid, also known as ethanoic acid, is an organic [i] chemical compound [i] ... 

, the ester is called an acetate. Esters may also be formed with inorganic acids; for example, dimethyl sulfate Dimethyl sulfate

Dimethyl sulfate is a chemical compound [i] with formula [i]22. ... 

 is an ester, and sometimes called "sulfuric acid Sulfuric acid

Sulfuric acid , H [i]2S [i]O [i]4, is a strong mineral acid [i]. ... 

, dimethyl ester".

Esters are named similarly to salt Salt

In chemistry [i], a salt is any ionic compound [i] composed of cation [i]s and anion [i]s so that the ... 

s; 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.

An ester can be thought of as a product of a condensation reaction Condensation reaction

A condensation reaction is a chemical reaction [i] in which two molecule [i]s or moieties [i] rea ... 

 of an acid and an alcohol Alcohol

In chemistry [i], an alcohol is any organic compound [i] in which a hydroxyl [i] group [i] ... 

 , although there are other ways to form esters. Condensation is a type of chemical reaction Chemical reaction

A chemical reaction is a process that results in the interconversion of chemical substance [i]s . ... 

 in which two molecule Molecule

In chemistry, a molecule is an aggregate of two or more atom [i]s in a definite arrangement held togethe ... 

s are joined together and eliminate a small molecule, in this case two-OH groups are joined eliminating a water molecule Water

Water is a taste [i]less, odor [i]less substance that is essential to all known forms of life [i] and i ... 

. 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 Catalyst

In chemistry, a catalyst is a substance [i] that decreases the activation energy [i] ... 

 for this reaction. The name ester is derived from the German Essig-Äther, an old name for acetic acid ethyl ester .

Naming of esters


Esters can be produced by an equilibrium reaction between an alcohol Alcohol

In chemistry [i], an alcohol is any organic compound [i] in which a hydroxyl [i] group [i] ... 

 and a carboxylic acid Carboxylic acid

Carboxylic acids are organic acid [i]s characterized by the presence of a carboxyl group, which ha ... 

. The ester is named according to the alkyl Alkyl

An alkyl is a univalent [i] radical [i] containing only carbon [i] and hydrogen [i] atoms arrang ... 

group and then the alkanoate which make it up. For example, the reaction between methanol Methanol

Methanol, also known as methyl alcohol or wood alcohol, is a chemical compound [i] with chemical formula [i] ... 

 and butyric acid Butyric acid

Butyric acid, IUPAC [i] name n-Butanoic acid, or normal butyric acid, is a carboxylic acid [i] ... 

 yields the ester methyl butyrate Methyl butyrate

Methyl butyrate is an ester [i] with a fruity fragrance resembling apple [i]s or pineapple [i]s.... 

 C3H7-COO-CH3 . The simplest ester is H-COO-CH3 .

For esters derived from the simplest carboxylic acids, the traditional names are recommended by IUPAC, 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 Methyl benzoate

Methyl benzoate is an ester [i] with the chemical formula [i] C6H5COOCH3. ... 

, and phthalates Phthalates

Phthalates, or phthalate esters, are a group of chemical compounds that are mainly used as plasticizer [i] ... 

, with substitution allowed in the name.

Physical properties

Esters participate in hydrogen bond Hydrogen bond

In chemistry [i], a hydrogen bond is a type of attractive intermolecular force [i] that exists between t ... 

s 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 Water

Water is a taste [i]less, odor [i]less substance that is essential to all known forms of life [i] and i ... 

-soluble than their parent hydrocarbon Hydrocarbon

[i] that consists only of the elements [[carbon]... 

s. 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 molecule Molecule

In chemistry, a molecule is an aggregate of two or more atom [i]s in a definite arrangement held togethe ... 

s cannot hydrogen-bond to each other, which makes esters generally more volatile than an carboxylic acid Carboxylic acid

Carboxylic acids are organic acid [i]s characterized by the presence of a carboxyl group, which ha ... 

 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

Gas-liquid chromatography, or simply gas chromatography, is a type of chromatography [i] in which ... 

, gas liquid chromatography Gas-liquid chromatography

Gas-liquid chromatography, or simply gas chromatography, is a type of chromatography [i] in which ... 

, or mass spectrometry Mass spectrometry

Mass spectrometry is an analytical technique used to measure the mass-to-charge ratio [i] of ion [i]s. ... 

.
Many esters have distinctive odors, which has led to their use as artificial flavorings and fragrances. For example:
allyl hexanoate pineapple Pineapple

The pineapple is a tropical [i] ground [i] and fruit [i] , native [i] to Brazil [i], Bolivia [i], ... 

benzyl acetate pear Pear

Pears are tree [i]s of the genus [i] Pyrus and the juicy fruit [i] of that tree, edible in some spec ... 

, strawberry Strawberry

The strawberry is a genus of plant [i]s in the family Rosaceae [i], and the fruit [i] of these plan ... 

, jasmine Jasmine

Jasmine is a genus of shrub [i]s and vine [i]s in the Family Oleaceae [i], with about 200 species, nativ ... 

bornyl acetate pine Pine

Pines are coniferous [i] tree [i]s of the genus Pinus, in the family Pinaceae [i]. ... 

 tree flavor
butyl butyrate Butyl butyrate

Butyl butyrate, or butyl butanoate, is an organic compound [i] which is an ester [i] formed by the conde ... 

pineapple Pineapple

The pineapple is a tropical [i] ground [i] and fruit [i] , native [i] to Brazil [i], Bolivia [i], ... 

ethyl acetate Ethyl acetate

Ethyl acetate is the organic compound [i] with the formula CH3CH2OC(O)CH3. ... 

peach Peach

The Peach is a tree [i] native to China [i] that bears a juicy fruit of the same name.
... 

, pineapple Pineapple

The pineapple is a tropical [i] ground [i] and fruit [i] , native [i] to Brazil [i], Bolivia [i], ... 

, raspberry Raspberry

The Raspberry or Red Raspberry is a plant [i] that produces a tart, sweet, red composite fruit [i] ... 

ethyl butyrate Ethyl butyrate

Ethyl butyrate, also known as ethyl butanoate, is an ester [i] with the chemical formula CH3CH2CH2 ... 

banana Banana

Banana is the common name [i] used for herbaceous plants in the genus [i] Musa [i], which beca ... 

, pineapple Pineapple

The pineapple is a tropical [i] ground [i] and fruit [i] , native [i] to Brazil [i], Bolivia [i], ... 

, strawberry Strawberry

The strawberry is a genus of plant [i]s in the family Rosaceae [i], and the fruit [i] of these plan ... 

ethyl hexanoate strawberry Strawberry

The strawberry is a genus of plant [i]s in the family Rosaceae [i], and the fruit [i] of these plan ... 

ethyl cinnamate Ethyl cinnamate

Ethyl cinnamate is the ester [i] of cinnamic acid [i] and ethyl alcohol [i]. ... 

cinnamon Cinnamon

Cinnamon is a small evergreen [i] tree [i] 10-15 m tall, belonging to the family Lauraceae [i], native ... 

ethyl formate Ethyl formate

Ethyl formate is an ester [i] formed when ethanol [i] reacts with formic acid [i]. ... 

lemon Lemon

The lemon is a hybrid [i] citrus [i] tree [i] of cultivated origin. ... 

, rum Rum

Rum is a distilled beverage [i] made from sugarcane [i] by-products such as molasses [i] and sugarcane juice [i]... 

, strawberry Strawberry

The strawberry is a genus of plant [i]s in the family Rosaceae [i], and the fruit [i] of these plan ... 

ethyl heptanoate Ethyl heptanoate

Ethyl heptanoate is the ester [i] resulting from the condensation of heptanoic acid [i] and ethanol [i]. ... 

apricot Apricot

The apricot is a fruit [i]-bearing tree [i] native to China [i]. ... 

, cherry Cherry

A cherry is both a tree [i] and its fleshy fruit [i], a type known as a drupe [i] with a single hard st ... 

, grape Grape

Grapes are the fruit [i] that grow on a woody grape vine [i]. ... 

, raspberry Raspberry

The Raspberry or Red Raspberry is a plant [i] that produces a tart, sweet, red composite fruit [i] ... 

ethyl isovalerate apple Apple

The apple is a tree [i] and its pomaceous [i] fruit [i], of the species Malus domestica in the ... 

ethyl lactate Ethyl lactate

Ethyl lactate, also known as lactic acid ethyl ester, is a monobasic ester [i] formed from lactic acid [i] ... 

grape Grape

Grapes are the fruit [i] that grow on a woody grape vine [i]. ... 

ethyl nonanoate grape Grape

Grapes are the fruit [i] that grow on a woody grape vine [i]. ... 

ethyl valerate Ethyl pentanoate

Ethyl pentanoate, also commonly known as ethyl valerate, is an organic compound [i] used in flavors.... 

apple Apple

The apple is a tree [i] and its pomaceous [i] fruit [i], of the species Malus domestica in the ... 

geranyl acetate Geranyl acetate

Geranyl acetate is a natural organic compound [i] that is classified as a monoterpene [i]. ... 

geranium
geranyl butyrate cherry Cherry

A cherry is both a tree [i] and its fleshy fruit [i], a type known as a drupe [i] with a single hard st ... 

geranyl pentanoate apple Apple

The apple is a tree [i] and its pomaceous [i] fruit [i], of the species Malus domestica in the ... 

isobutyl acetate Isobutyl acetate

The chemical compound [i] isobutyl acetate, with systematic name 2-methylpropyl ethanoate, is a co ... 

cherry Cherry

A cherry is both a tree [i] and its fleshy fruit [i], a type known as a drupe [i] with a single hard st ... 

, raspberry Raspberry

The Raspberry or Red Raspberry is a plant [i] that produces a tart, sweet, red composite fruit [i] ... 

, strawberry Strawberry

The strawberry is a genus of plant [i]s in the family Rosaceae [i], and the fruit [i] of these plan ... 

isobutyl formate raspberries
isopentyl acetate Isoamyl acetate

Isoamyl acetate is an organic compound [i] that is the ester [i] formed from isoamyl alcohol [i] and acetic acid [i] ... 

pear Pear

Pears are tree [i]s of the genus [i] Pyrus and the juicy fruit [i] of that tree, edible in some spec ... 

,banana Banana

Banana is the common name [i] used for herbaceous plants in the genus [i] Musa [i], which beca ... 

linalyl acetate lavender Lavender

The lavenders Lavandula are a genus [i] of about 25-30 species of flowering plant [i]s in the mint f ... 

, sage
linalyl butyrate peach Peach

The Peach is a tree [i] native to China [i] that bears a juicy fruit of the same name.
... 

linalyl formate apple Apple

The apple is a tree [i] and its pomaceous [i] fruit [i], of the species Malus domestica in the ... 

, peach Peach

The Peach is a tree [i] native to China [i] that bears a juicy fruit of the same name.
... 

menthyl acetate peppermint Peppermint

Peppermint is a sterile [i] hybrid [i] mint [i], a cross between watermint [i] and spearmint [i] ... 

methyl anthranilate grape Grape

Grapes are the fruit [i] that grow on a woody grape vine [i]. ... 

, jasmine Jasmine

Jasmine is a genus of shrub [i]s and vine [i]s in the Family Oleaceae [i], with about 200 species, nativ ... 

methyl benzoate Methyl benzoate

Methyl benzoate is an ester [i] with the chemical formula [i] C6H5COOCH3. ... 

fruity, ylang ylang Ylang-ylang

Ylang-ylang, Cananga odorata, is the flower of the cananga tree.... 

methyl benzyl acetate cherry Cherry

A cherry is both a tree [i] and its fleshy fruit [i], a type known as a drupe [i] with a single hard st ... 

methyl butyrate Methyl butyrate

Methyl butyrate is an ester [i] with a fruity fragrance resembling apple [i]s or pineapple [i]s.... 

pineapple Pineapple

The pineapple is a tropical [i] ground [i] and fruit [i] , native [i] to Brazil [i], Bolivia [i], ... 

, apple Apple

The apple is a tree [i] and its pomaceous [i] fruit [i], of the species Malus domestica in the ... 

methyl cinnamate strawberry Strawberry

The strawberry is a genus of plant [i]s in the family Rosaceae [i], and the fruit [i] of these plan ... 

methyl pentanoate flowery Flower

A flower,rflorem<flos), also known as a bloom or blossom, is the reprod ... 

methyl phenyl acetate honey Honey

Honey is a sweet and viscous fluid produced by honeybee [i]s from the nectar [i] of flower [i]s. ... 

methyl salicylate Methyl salicylate

Methyl salicylateCOOCH3; is a natural product of many species of plant [i]s. ... 

root beer Root beer

Root beer is a fermented [i] beverage [i] made from a combination of vanilla [i], cherry [i] ... 

, wintergreen, Germolene™ and Ralgex™ ointments
nonyl caprylate orange
octyl acetate Octyl acetate

Octyl acetate is an ester [i] that is formed from octanol [i] and acetic acid [i].... 

fruity-orange
octyl butyrate parsnip Parsnip

The parsnip is a root vegetable [i] related to the carrot [i]. ... 

pentyl acetate Amyl acetate

Amyl acetate is an organic compound [i] and an ester [i] with the chemical formula CH [i]3COO [i] ... 

apple Apple

The apple is a tree [i] and its pomaceous [i] fruit [i], of the species Malus domestica in the ... 

, banana Banana

Banana is the common name [i] used for herbaceous plants in the genus [i] Musa [i], which beca ... 

pentyl butyrate Pentyl butyrate

Pentyl butyrate, also known as pentyl butanoate or amyl butyrate, is an ester [i] that is fo ... 

apricot Apricot

The apricot is a fruit [i]-bearing tree [i] native to China [i]. ... 

, pear Pear

Pears are tree [i]s of the genus [i] Pyrus and the juicy fruit [i] of that tree, edible in some spec ... 

, pineapple Pineapple

The pineapple is a tropical [i] ground [i] and fruit [i] , native [i] to Brazil [i], Bolivia [i], ... 

pentyl hexanoate apple Apple

The apple is a tree [i] and its pomaceous [i] fruit [i], of the species Malus domestica in the ... 

, pineapple Pineapple

The pineapple is a tropical [i] ground [i] and fruit [i] , native [i] to Brazil [i], Bolivia [i], ... 

pentyl pentanoate Pentyl pentanoate

Pentyl pentanoate is an ester [i] used in dilute quantities to replicate the scent or flavour of apple [i]... 

apple Apple

The apple is a tree [i] and its pomaceous [i] fruit [i], of the species Malus domestica in the ... 

propyl isobutyrate rum Rum

Rum is a distilled beverage [i] made from sugarcane [i] by-products such as molasses [i] and sugarcane juice [i]... 

terpenyl butyrate cherry Cherry

A cherry is both a tree [i] and its fleshy fruit [i], a type known as a drupe [i] with a single hard st ... 


Ester synthesis

Esters can be prepared in the laboratory in several ways:
  • by esterification of carboxylic acid Carboxylic acid

    Carboxylic acids are organic acid [i]s characterized by the presence of a carboxyl group, which ha ... 

     derivatives and alcohol Alcohol

    In chemistry [i], an alcohol is any organic compound [i] in which a hydroxyl [i] group [i] ... 

    s
  • by transesterifications between other esters
  • by Dieckmann condensation Dieckmann condensation

    The Dieckmann condensation [i] is the intramolecular [i] chemical reaction [i] of diester [i]s with base to gi... 

     or Claisen condensation Claisen condensation

    The Claisen condensation is a carbon-carbon bond [i] forming reaction [i] that occurs b ... 

     of esters carrying acidic a-protons
  • by Favorskii rearrangement Favorskii rearrangement

    The Favorskii rearrangement is the transformation of haloketone [i]s to branched-chain or ring-contracte ... 

     of a-haloketones in presence of base
  • by nucleophilic displacement Nucleophilic substitution

    In chemistry [i], nucleophilic substitution is a class of substitution reaction [i] in which an electron ... 

     of alkyl halide Haloalkane

    The haloalkanes are a group of chemical compound [i]s, consisting of alkane [i]s, such as methane [i] or ... 

    s with carboxylic acid salts
  • by Baeyer-Villiger oxidation Baeyer-Villiger oxidation

    The Baeyer-Villiger oxidation is an organic reaction [i] in which a ketone [i] is oxidized [i] to ... 

     of ketones with peroxides
  • by Pinner reaction Pinner reaction

    The Pinner reaction is an organic reaction [i] of a nitrile [i] with an alcohol [i] under acid [i] catalysis [i] ... 

     of nitrile Nitrile

    [i] [[functional group]... 

    s with an alcohol

Ester reactions


Esters react in a number of ways:
  • Esters may undergo hydrolysis Hydrolysis

    Hydrolysis is a chemical reaction [i] or process in which a molecule [i] is split into two parts by reac ... 

     - the breakdown of an ester by water. This process can be catalyzed both by acids and bases. The base-catalyzed process is called saponification Saponification

    Saponification is the hydrolysis [i] of an ester [i] under basic [i] conditions to form an alcohol [i] ... 

    . The hydrolysis yields an alcohol and a carboxylic acid Carboxylic acid

    Carboxylic acids are organic acid [i]s characterized by the presence of a carboxyl group, which ha ... 

     or its carboxylate Carboxylic acid

    Carboxylic acids are organic acid [i]s characterized by the presence of a carboxyl group, which ha ... 

     salt Salt

    In chemistry [i], a salt is any ionic compound [i] composed of cation [i]s and anion [i]s so that the ... 

    .
  • Esters also react if heated with primary or secondary amine Amine

    Amines are organic compound [i]s and a type of functional group [i] that contain nitrogen [i] as the key ... 

    s, producing amide Amide

    n chemistry [i], an amide is one of two kinds of compound [i]s:

... 

s.
  • Phenyl esters react to hydroxyarylketones in the Fries rearrangement Fries rearrangement

    The Fries rearrangement is a rearrangement reaction [i] of a phenyl [i] ester [i] to a hydroxy [i] aryl [i]... 

    .
  • Di-esters such as diethyl malonate Diethyl malonate

    Diethyl malonate, also known as DEM, is the diethyl [i] ester [i] of malonic acid [i]. ... 

     react as nucleophile Nucleophile

    In chemistry [i], a nucleophile is a reagent [i] that forms a chemical bond [i] to its reaction partner ... 

     with alkyl halide Haloalkane

    The haloalkanes are a group of chemical compound [i]s, consisting of alkane [i]s, such as methane [i] or ... 

    s in the malonic ester synthesis Malonic ester synthesis

    The Malonic Ester Synthesis is a chemical reaction [i] where diethyl malonate [i] is alkylated [i] ... 

     after deprotonation.
  • Specific esters are functionalized with an a-hydroxyl group in the Chan rearrangement Chan rearrangement

    The Chan rearrangement is a chemical reaction [i] that involves rearranging [i] a ... 

  • Esters are converted to isocyanates through intermediate hydroxamic acids in the Lossen rearrangement Lossen rearrangement

    The Lossen rearrangement [i] is the chemical reaction [i] of a hydroxamic acid [i] 1 with a dehydration ... 

    .

See also

  • Methyl

External links

  • A simple guide to naming and making Esters, as well as the Chemistry behind it.

References