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94-433: Hall launched the brand with two expressions called Forty Creek Barrel Select and Forty Creek Three Grain. In 2007, the first of a series of Forty Creek Special Reserves bottlings were released, which are limited-edition expressions that vary with each lot. In 2012, Forty Creek Copper Pot and Forty Creek Cream were introduced. Bill Ashburn, Forty Creek's Master Blender, has been a part of the distillery since John Hall acquired

188-405: A Latin prefix, and undecane which has mixed-language prefixes. Cyclic alkanes are simply prefixed with "cyclo-": for example, C 4 H 8 is cyclobutane (not to be confused with butene ) and C 6 H 12 is cyclohexane (not to be confused with hexene ). Branched alkanes are named as a straight-chain alkane with attached alkyl groups. They are prefixed with a number indicating

282-561: A blood alcohol concentration of 0.03-0.05 % and induces anesthetic coma at 0.4%. This use carries the high risk of deadly alcohol intoxication , pulmonary aspiration and vomit, which led to use of alternatives in antiquity, such as opium and cannabis , and later diethyl ether, starting in the 1840s. Ethanol is used as an antiseptic in medical wipes and hand sanitizer gels for its bactericidal and anti-fungal effects. Ethanol kills microorganisms by dissolving their membrane lipid bilayer and denaturing their proteins , and

376-468: A fuel source for lamps, stoves, and internal combustion engines. Ethanol also can be dehydrated to make ethylene, an important chemical feedstock. As of 2023, world production of ethanol fuel was 29,590,000,000 US gallons (112.0 gigalitres), coming mostly from the U.S. (51%) and Brazil (26%). Ethanol is the systematic name defined by the International Union of Pure and Applied Chemistry for

470-414: A hydroxyl group ), which indicates that the carbon of a methyl group (CH 3 −) is attached to the carbon of a methylene group (−CH 2 –), which is attached to the oxygen of a hydroxyl group (−OH). It is a constitutional isomer of dimethyl ether . Ethanol is sometimes abbreviated as EtOH , using the common organic chemistry notation of representing the ethyl group (C 2 H 5 −) with Et . Ethanol

564-447: A benzene ring are structural analogs of benzoic acid ( Ph −COOH ) and are named as one of its derivatives. If there are multiple carboxyl groups on the same parent chain, multiplying prefixes are used: Malonic acid , CH 2 (COOH) 2 , is systematically named propanedioic acid. Alternatively, the suffix "-carboxylic acid" can be used in place of "oic acid", combined with a multiplying prefix if necessary – mellitic acid

658-466: A compound consisting of an alkyl group with two carbon atoms (prefix "eth-"), having a single bond between them (infix "-an-") and an attached −OH functional group (suffix "-ol"). The "eth-" prefix and the qualifier "ethyl" in "ethyl alcohol" originally came from the name "ethyl" assigned in 1834 to the group C 2 H 5 − by Justus Liebig . He coined the word from the German name Aether of

752-472: A cosmetic, and retained that meaning in Middle Latin . The use of 'alcohol' for ethanol (in full, "alcohol of wine") was first recorded in 1753. Before the late 18th century the term alcohol generally referred to any sublimated substance. Ethanol is the oldest known sedative , used as an oral general anesthetic during surgery in ancient Mesopotamia and in medieval times . Mild intoxication starts at

846-457: A fuel reduces harmful tailpipe emissions of carbon monoxide, particulate matter, oxides of nitrogen , and other ozone-forming pollutants. Argonne National Laboratory analyzed greenhouse gas emissions of many different engine and fuel combinations, and found that biodiesel /petrodiesel blend ( B20 ) showed a reduction of 8%, conventional E85 ethanol blend a reduction of 17% and cellulosic ethanol 64%, compared with pure gasoline. Ethanol has

940-499: A greater concentration of sucrose than corn (by about 30%), but is also much easier to extract. The bagasse generated by the process is not discarded, but burned by power plants to produce electricity. Bagasse burning accounts for around 9% of the electricity produced in Brazil. In the 1970s most industrial ethanol in the U.S. was made as a petrochemical, but in the 1980s the U.S. introduced subsidies for corn-based ethanol . According to

1034-461: A much greater research octane number (RON) than gasoline, meaning it is less prone to pre-ignition, allowing for better ignition advance which means more torque, and efficiency in addition to the lower carbon emissions. Ethanol combustion in an internal combustion engine yields many of the products of incomplete combustion produced by gasoline and significantly larger amounts of formaldehyde and related species such as acetaldehyde. This leads to

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1128-410: A numerical suffix indicating the bonding position: CH 3 CH 2 CH 2 OH is propan-1-ol. The suffixes -diol , -triol , -tetrol , etc., are used for multiple −OH groups: Ethylene glycol CH 2 OHCH 2 OH is ethane-1,2-diol. If higher precedence functional groups are present (see order of precedence , below), the prefix "hydroxy" is used with the bonding position: CH 3 CHOHCOOH

1222-509: A post-processing solvent to remove oils, waxes, and chlorophyll from solution in a process known as winterization . Ethanol is found in paints , tinctures, markers, and personal care products such as mouthwashes, perfumes and deodorants. Polysaccharides precipitate from aqueous solution in the presence of alcohol, and ethanol precipitation is used for this reason in the purification of DNA and RNA . Because of its low freezing point of −114 °C (−173 °F) and low toxicity, ethanol

1316-586: A resolution on naming alcohols and phenols that was adopted at the International Conference on Chemical Nomenclature that was held in April 1892 in Geneva , Switzerland. The term alcohol now refers to a wider class of substances in chemistry nomenclature, but in common parlance it remains the name of ethanol. It is a medieval loan from Arabic al-kuḥl , a powdered ore of antimony used since antiquity as

1410-416: A significantly larger photochemical reactivity and more ground level ozone . This data has been assembled into The Clean Fuels Report comparison of fuel emissions and show that ethanol exhaust generates 2.14 times as much ozone as gasoline exhaust. When this is added into the custom Localized Pollution Index of The Clean Fuels Report, the local pollution of ethanol (pollution that contributes to smog)

1504-400: A solvent is in making tincture of iodine, cough syrups, etc. It is also miscible with light aliphatic hydrocarbons, such as pentane and hexane , and with aliphatic chlorides such as trichloroethane and tetrachloroethylene . Ethanol's miscibility with water contrasts with the immiscibility of longer-chain alcohols (five or more carbon atoms), whose water miscibility decreases sharply as

1598-399: A systematic and a common name (like CH 3 COOH , for example, which is known as both acetic acid and as ethanoic acid), its salts can be named from either parent name. Thus, KCH 3 CO 2 can be named as potassium acetate or as potassium ethanoate. The prefix form, is "carboxylato-". Esters ( R−C(=O)O−R' ) are named as alkyl derivatives of carboxylic acids. The alkyl (R') group

1692-405: A temperature called its flash point and an ignition source is then applied to it. For 20% alcohol by mass (about 25% by volume), this will occur at about 25 °C (77 °F). The flash point of pure ethanol is 13 °C (55 °F), but may be influenced very slightly by atmospheric composition such as pressure and humidity. Ethanol mixtures can ignite below average room temperature. Ethanol

1786-443: Is N , N -dimethylethanamide. Nitriles ( R−C≡N ) are named by adding the suffix "-nitrile" to the longest hydrocarbon chain (including the carbon of the cyano group). It can also be named by replacing the "-oic acid" of their corresponding carboxylic acids with "-carbonitrile." The prefix form is "cyano-." Functional class IUPAC nomenclature may also be used in the form of alkyl cyanides. For example, CH 3 CH 2 CH 2 CH 2 C≡N

1880-418: Is N ,2-dimethylpropanamine. * Note : These suffixes, in which the carbon atom is counted as part of the preceding chain, are the most commonly used. See individual functional group articles for more details. The order of remaining functional groups is only needed for substituted benzene and hence is not mentioned here. Common nomenclature uses the older names for some organic compounds instead of using

1974-411: Is 2-hydroxypropanoic acid. Ethers ( R−O−R ) consist of an oxygen atom between the two attached carbon chains. The shorter of the two chains becomes the first part of the name with the -ane suffix changed to -oxy, and the longer alkane chain becomes the suffix of the name of the ether. Thus, CH 3 OCH 3 is methoxymethane, and CH 3 OCH 2 CH 3 is methoxyethane ( not ethoxymethane). If

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2068-480: Is IUPAC convention to describe all alkenes using absolute descriptors of Z- (same side) and E- (opposite) with the Cahn–Ingold–Prelog priority rules (see also E–Z notation ). Alkynes are named using the same system, with the suffix " -yne " indicating a triple bond: ethyne ( acetylene ), propyne ( methylacetylene ). In haloalkanes and haloarenes ( R−X ), Halogen functional groups are prefixed with

2162-419: Is a volatile , flammable , colorless liquid with a characteristic wine -like odor and pungent taste. In nature, grape-sugar breaks up by the action of fermentation into alcohol or carbonic acid, without anything being added. As a psychoactive depressant , it is the active ingredient in alcoholic beverages , and the second most consumed drug globally behind caffeine . Ethanol is naturally produced by

2256-557: Is a volatile, colorless liquid that has a slight odor. It burns with a smokeless blue flame that is not always visible in normal light. The physical properties of ethanol stem primarily from the presence of its hydroxyl group and the shortness of its carbon chain. Ethanol's hydroxyl group is able to participate in hydrogen bonding, rendering it more viscous and less volatile than less polar organic compounds of similar molecular weight, such as propane . Ethanol's adiabatic flame temperature for combustion in air is 2082 °C or 3779 °F. Ethanol

2350-524: Is also an IUPAC nomenclature of inorganic chemistry . To avoid long and tedious names in normal communication, the official IUPAC naming recommendations are not always followed in practice, except when it is necessary to give an unambiguous and absolute definition to a compound. IUPAC names can sometimes be simpler than older names, as with ethanol , instead of ethyl alcohol. For relatively simple molecules they can be more easily understood than non-systematic names, which must be learnt or looked over. However,

2444-404: Is an image of the same molecule, where the hydrogens in the parent chain are removed and the carbons are shown by their numbers: Now, following the above steps: The final name is (6 E ,13 E )-18-bromo-12-butyl-11-chloro-4,8-diethyl-5-hydroxy-15-methoxytricosa-6,13-dien-19-yne-3,9-dione. Straight-chain alkanes take the suffix " -ane " and are prefixed depending on the number of carbon atoms in

2538-699: Is another potential source of ethanol, and is suitable for growing in dryland conditions. The International Crops Research Institute for the Semi-Arid Tropics is investigating the possibility of growing sorghum as a source of fuel, food, and animal feed in arid parts of Asia and Africa . Sweet sorghum has one-third the water requirement of sugarcane over the same time period. It also requires about 22% less water than corn. The world's first sweet sorghum ethanol distillery began commercial production in 2007 in Andhra Pradesh , India . Ethanol has been produced in

2632-563: Is as an engine fuel and fuel additive . Brazil in particular relies heavily upon the use of ethanol as an engine fuel, due in part to its role as one of the world's leading producers of ethanol. Gasoline sold in Brazil contains at least 25% anhydrous ethanol. Hydrous ethanol (about 95% ethanol and 5% water) can be used as fuel in more than 90% of new gasoline-fueled cars sold in the country. The US and many other countries primarily use E10 (10% ethanol, sometimes known as gasohol) and E85 (85% ethanol) ethanol/gasoline mixtures. Over time, it

2726-463: Is being conducted at a research level although there are a number of organizations at the beginning of the commercialization of ethanol fuel cells. Ethanol fireplaces can be used for home heating or for decoration. Ethanol can also be used as stove fuel for cooking. As a central nervous system depressant , ethanol is one of the most commonly consumed psychoactive drugs . Despite alcohol's psychoactive, addictive, and carcinogenic properties, it

2820-439: Is believed that a material portion of the ≈150-billion-US-gallon (570,000,000 m ) per year market for gasoline will begin to be replaced with fuel ethanol. Australian law limits the use of pure ethanol from sugarcane waste to 10 % in automobiles. Older cars (and vintage cars designed to use a slower burning fuel) should have the engine valves upgraded or replaced. According to an industry advocacy group , ethanol as

2914-410: Is benzenehexacarboxylic acid, for example. In the latter case, the carbon atoms in the carboxyl groups do not count as being part of the main chain, a rule that also applies to the prefix form "carboxy-". Citric acid serves as an example: it is formally named 2-hydroxypropane-1,2,3-tricarboxylic acid rather than 3-carboxy-3-hydroxypentanedioic acid . Salts of carboxylic acids are named following

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3008-419: Is called ethanoyl-R. Simply add the name of the attached halide to the end of the acyl group. For example, CH 3 COCl is ethanoyl chloride. An alternate suffix is "-carbonyl halide" as opposed to "-oyl halide". The prefix form is "halocarbonyl-". Acid anhydrides ( R−C(=O)−O−C(=O)−R ) have two acyl groups linked by an oxygen atom. If both acyl groups are the same, then the name of the carboxylic acid with

3102-523: Is called pentanenitrile or butyl cyanide. Cycloalkanes and aromatic compounds can be treated as the main parent chain of the compound, in which case the positions of substituents are numbered around the ring structure. For example, the three isomers of xylene CH 3 C 6 H 4 CH 3 , commonly the ortho- , meta- , and para- forms, are 1,2-dimethylbenzene, 1,3-dimethylbenzene, and 1,4-dimethylbenzene. The cyclic structures can also be treated as functional groups themselves, in which case they take

3196-481: Is considered a flammable liquid (Class 3 Hazardous Material) in concentrations above 2.35% by mass (3.0% by volume; 6 proof ). Dishes using burning alcohol for culinary effects are called flambé . Ethanol is a byproduct of the metabolic process of yeast. As such, ethanol will be present in any yeast habitat. Ethanol can commonly be found in overripe fruit. Ethanol produced by symbiotic yeast can be found in bertam palm blossoms. Although some animal species, such as

3290-439: Is considered a universal solvent , as its molecular structure allows for the dissolving of both polar , hydrophilic and nonpolar , hydrophobic compounds. As ethanol also has a low boiling point , it is easy to remove from a solution that has been used to dissolve other compounds, making it a popular extracting agent for botanical oils. Cannabis oil extraction methods often use ethanol as an extraction solvent, and also as

3384-451: Is currently used in lightweight rocket-powered racing aircraft . Commercial fuel cells operate on reformed natural gas, hydrogen or methanol. Ethanol is an attractive alternative due to its wide availability, low cost, high purity and low toxicity. There is a wide range of fuel cell concepts that have entered trials including direct-ethanol fuel cells , auto-thermal reforming systems and thermally integrated systems. The majority of work

3478-410: Is effective against most bacteria , fungi and viruses . It is ineffective against bacterial spores , which can be treated with hydrogen peroxide . A solution of 70% ethanol is more effective than pure ethanol because ethanol relies on water molecules for optimal antimicrobial activity. Absolute ethanol may inactivate microbes without destroying them because the alcohol is unable to fully permeate

3572-406: Is especially useful when both groups attached to the oxygen atom are complex. Aldehydes ( R−CH=O ) take the suffix " -al ". If other functional groups are present, the chain is numbered such that the aldehyde carbon is in the "1" position, unless functional groups of higher precedence are present. If a prefix form is required, "oxo-" is used (as for ketones), with the position number indicating

3666-429: Is less expensive and more readily available than fomepizole in the role. Ethanol is used to dissolve many water-insoluble medications and related compounds. Liquid preparations of pain medications , cough and cold medicines , and mouth washes, for example, may contain up to 25% ethanol and may need to be avoided in individuals with adverse reactions to ethanol such as alcohol-induced respiratory reactions . Ethanol

3760-433: Is more economical depends on prevailing prices of petroleum and grain feed stocks. World production of ethanol in 2006 was 51 gigalitres (1.3 × 10  US gal), with 69% of the world supply coming from Brazil and the U.S. Brazilian ethanol is produced from sugarcane, which has relatively high yields (830% more fuel than the fossil fuels used to produce it) compared to some other energy crops . Sugarcane not only has

3854-585: Is more economical. In an older process, first practiced on the industrial scale in 1930 by Union Carbide but now almost entirely obsolete, ethylene was hydrated indirectly by reacting it with concentrated sulfuric acid to produce ethyl sulfate , which was hydrolyzed to yield ethanol and regenerate the sulfuric acid: Ethanol in alcoholic beverages and fuel is produced by fermentation. Certain species of yeast (e.g., Saccharomyces cerevisiae ) metabolize sugar (namely polysaccharides ), producing ethanol and carbon dioxide. The chemical equations below summarize

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3948-453: Is named 2-methylbutane, not 3-methylbutane. If there are multiple side-branches of the same size alkyl group, their positions are separated by commas and the group prefixed with multiplier prefixes depending on the number of branches. For example, C(CH 3 ) 4 (neopentane) is named 2,2-dimethylpropane. If there are different groups, they are added in alphabetical order, separated by commas or hyphens. The longest possible main alkane chain

4042-659: Is named first. The R−C(=O)O part is then named as a separate word based on the carboxylic acid name, with the ending changed from "-oic acid" to " -oate " or "-carboxylate" For example, CH 3 CH 2 CH 2 CH 2 COOCH 3 is methyl pentanoate, and (CH 3 ) 2 CHCH 2 CH 2 COOCH 2 CH 3 is ethyl 4-methylpentanoate. For esters such as ethyl acetate ( CH 3 COOCH 2 CH 3 ), ethyl formate ( HCOOCH 2 CH 3 ) or dimethyl phthalate that are based on common acids, IUPAC recommends use of these established names, called retained names . The "-oate" changes to "-ate." Some simple examples, named both ways, are shown in

4136-449: Is no need to number it. The resulting name appears as: where each "#" represents a number. The group secondary functional groups and side chains may not look the same as shown here, as the side chains and secondary functional groups are arranged alphabetically. The di- and tri- have been used just to show their usage. (di- after #,#, tri- after #,#,#, etc.) Here is a sample molecule with the parent carbons numbered: For simplicity, here

4230-459: Is present mainly as an antimicrobial preservative in over 700 liquid preparations of medicine including acetaminophen , iron supplements , ranitidine , furosemide , mannitol , phenobarbital , trimethoprim/sulfamethoxazole and over-the-counter cough medicine . Some medicinal solutions of ethanol are also known as tinctures . In mammals, ethanol is primarily metabolized in the liver and stomach by ADH enzymes. These enzymes catalyze

4324-537: Is rated 1.7, where gasoline is 1.0 and higher numbers signify greater pollution. The California Air Resources Board formalized this issue in 2008 by recognizing control standards for formaldehydes as an emissions control group, much like the conventional NOx and reactive organic gases (ROGs). More than 20% of Brazilian cars are able to use 100% ethanol as fuel, which includes ethanol-only engines and flex-fuel engines. Flex-fuel engines in Brazil are able to work with all ethanol, all gasoline or any mixture of both. In

4418-457: Is readily available and legal for sale in many countries. There are laws regulating the sale, exportation/importation, taxation, manufacturing, consumption, and possession of alcoholic beverages. The most common regulation is prohibition for minors. Ethanol is an important industrial ingredient. It has widespread use as a precursor for other organic compounds such as ethyl halides , ethyl esters , diethyl ether, acetic acid, and ethyl amines . It

4512-463: Is slightly more refractive than water, having a refractive index of 1.36242 (at λ=589.3 nm and 18.35 °C or 65.03 °F). The triple point for ethanol is 150 ± 20 K . Ethanol is a versatile solvent, miscible with water and with many organic solvents, including acetic acid , acetone , benzene , carbon tetrachloride , chloroform , diethyl ether, ethylene glycol, glycerol , nitromethane , pyridine , and toluene . Its main use as

4606-414: Is sometimes used in laboratories (with dry ice or other coolants) as a cooling bath to keep vessels at temperatures below the freezing point of water. For the same reason, it is also used as the active fluid in alcohol thermometers . Ethanol is a 2-carbon alcohol . Its molecular formula is CH 3 CH 2 OH. The structure of the molecule of ethanol is CH 3 −CH 2 −OH (an ethyl group linked to

4700-412: Is used; therefore 3-ethyl-4-methylhexane instead of 2,3-diethylpentane, even though these describe equivalent structures. The di-, tri- etc. prefixes are ignored for the purpose of alphabetical ordering of side chains (e.g. 3-ethyl-2,4-dimethylpentane, not 2,4-dimethyl-3-ethylpentane). Alkenes are named for their parent alkane chain with the suffix " -ene " and a numerical root indicating the position of

4794-562: The IUPAC nomenclature of organic chemistry is a method of naming organic chemical compounds as recommended by the International Union of Pure and Applied Chemistry (IUPAC). It is published in the Nomenclature of Organic Chemistry (informally called the Blue Book ). Ideally, every possible organic compound should have a name from which an unambiguous structural formula can be created. There

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4888-506: The carboxyl functional group must take the "1" position on the main chain and so the locant need not be stated. For example, CH 3 −CH(OH)−COOH ( lactic acid ) is named 2-hydroxypropanoic acid with no "1" stated. Some traditional names for common carboxylic acids (such as acetic acid ) are in such widespread use that they are retained in IUPAC nomenclature, though systematic names like ethanoic acid are also used. Carboxylic acids attached to

4982-419: The carburetor ) and attribute the damage to the increased water retention by ethanol in fuel. Ethanol was commonly used as fuel in early bipropellant rocket (liquid-propelled) vehicles, in conjunction with an oxidizer such as liquid oxygen. The German A-4 ballistic rocket of World War II (better known by its propaganda name V-2 ), which is credited as having begun the space age, used ethanol as

5076-429: The fermentation process of sugars by yeasts or via petrochemical processes such as ethylene hydration. Historically it was used as a general anesthetic , and has modern medical applications as an antiseptic , disinfectant , solvent for some medications, and antidote for methanol poisoning and ethylene glycol poisoning . It is used as a chemical solvent and in the synthesis of organic compounds, and as

5170-407: The oxidation of ethanol into acetaldehyde (ethanal): When present in significant concentrations, this metabolism of ethanol is additionally aided by the cytochrome P450 enzyme CYP2E1 in humans, while trace amounts are also metabolized by catalase . The resulting intermediate, acetaldehyde, is a known carcinogen, and poses significantly greater toxicity in humans than ethanol itself. Many of

5264-449: The pentailed treeshrew , exhibit ethanol-seeking behaviors, most show no interest or avoidance of food sources containing ethanol. Ethanol is also produced during the germination of many plants as a result of natural anaerobiosis . Ethanol has been detected in outer space , forming an icy coating around dust grains in interstellar clouds . Minute quantity amounts (average 196 ppb ) of endogenous ethanol and acetaldehyde were found in

5358-491: The Renewable Fuels Association, as of 30 October 2007, 131 grain ethanol bio-refineries in the U.S. have the capacity to produce 7 × 10 ^  US gal (26,000,000 m ) of ethanol per year. An additional 72 construction projects underway (in the U.S.) can add 6.4 billion US gallons (24,000,000 m ) of new capacity in the next 18 months. In India ethanol is made from sugarcane. Sweet sorghum

5452-557: The United States, flex-fuel vehicles can run on 0% to 85% ethanol (15% gasoline) since higher ethanol blends are not yet allowed or efficient. Brazil supports this fleet of ethanol-burning automobiles with large national infrastructure that produces ethanol from domestically grown sugarcane. Ethanol's high miscibility with water makes it unsuitable for shipping through modern pipelines like liquid hydrocarbons. Mechanics have seen increased cases of damage to small engines (in particular,

5546-449: The Year" in 2007 because of his contribution to new lines of thought and new methods in the world of whisky. Forty Creek has garnered a number of awards at Spirit ratings competitions and from rating organizations. The awards include: In the 2008 Icons of Whisky Canada competition held by London England's Whisky Magazine , John K. Hall was awarded Ambassador of the Year and Kittling Ridge

5640-487: The aged whiskies after they are blended, for an additional six months. The production of limited edition Forty Creek whiskies began in 2007. Typically, the bottles are individually numbered, the public has a period of time in which they can reserve a particular bottle number, and the whisky is released in September – followed by a special weekend of events at the distillery. Malt Advocate magazine named John Hall "Pioneer of

5734-403: The attached alkane chain with the suffix "-amine" (e.g., CH 3 NH 2 methanamine). If necessary, the bonding position is suffixed: CH 3 CH 2 CH 2 NH 2 propan-1-amine, CH 3 CHNH 2 CH 3 propan-2-amine. The prefix form is "amino-". For secondary amines (of the form R−NH−R ), the longest carbon chain attached to the nitrogen atom becomes the primary name of the amine;

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5828-418: The bonding position and take the form of fluoro-, chloro-, bromo-, iodo-, etc., depending on the halogen. Multiple groups are dichloro-, trichloro-, etc., and dissimilar groups are ordered alphabetically as before. For example, CHCl 3 ( chloroform ) is trichloromethane. The anesthetic halothane ( CF 3 CHBrCl ) is 2-bromo-2-chloro-1,1,1-trifluoroethane. Alcohols ( R−OH ) take the suffix " -ol " with

5922-416: The carbon in the amide group cannot be included in the main chain. The prefix form is "carbamoyl-". e.g., HCONH 2 methanamide, CH 3 CONH 2 ethanamide. Amides that have additional substituents on the nitrogen are treated similarly to the case of amines: they are ordered alphabetically with the location prefix N : HCON(CH 3 ) 2 is N , N -dimethylmethanamide, CH 3 CON(CH 3 ) 2

6016-406: The carbon the group is attached to, counting from the end of the alkane chain. For example, (CH 3 ) 2 CHCH 3 , commonly known as isobutane , is treated as a propane chain with a methyl group bonded to the middle (2) carbon, and given the systematic name 2-methylpropane. However, although the name 2-methylpropane could be used, it is easier and more logical to call it simply methylpropane –

6110-450: The carbon with the lower number for each double bond in the chain: CH 2 =CHCH 2 CH 3 is but-1-ene. Multiple double bonds take the form -diene, -triene, etc., with the size prefix of the chain taking an extra "a": CH 2 =CHCH=CH 2 is buta-1,3-diene. Simple cis and trans isomers may be indicated with a prefixed cis- or trans- : cis -but-2-ene, trans -but-2-ene. However, cis- and trans- are relative descriptors. It

6204-411: The chain, following standard rules. The first few are: For example, the simplest alkane is CH 4 methane, and the nine-carbon alkane CH 3 (CH 2 ) 7 CH 3 is named nonane . The names of the first four alkanes were derived from methanol , ether , propionic acid and butyric acid , respectively. The rest are named with a Greek numeric prefix, with the exceptions of nonane which has

6298-466: The characteristic alcohol flush reaction that can cause temporary reddening of the skin as well as a number of related, and often unpleasant, symptoms of acetaldehyde toxicity. This mutation is typically accompanied by another mutation in the ADH enzyme ADH1B in roughly 80 % of east Asians, which improves the catalytic efficiency of converting ethanol into acetaldehyde. The largest single use of ethanol

6392-540: The common or trivial name is often substantially shorter and clearer, and so preferred. These non-systematic names are often derived from an original source of the compound. Also, very long names may be less clear than structural formulas. In chemistry, a number of prefixes , suffixes and infixes are used to describe the type and position of the functional groups in the compound. The steps for naming an organic compound are: The numbers for that type of side chain will be grouped in ascending order and written before

6486-454: The composition of the ethanol-water azeotrope shifts to more ethanol-rich mixtures. The minimum-pressure azeotrope has an ethanol fraction of 100% and a boiling point of 306 K (33 °C), corresponding to a pressure of roughly 70  torr (9.333 kPa). Below this pressure, there is no azeotrope, and it is possible to distill absolute ethanol from an ethanol-water mixture. An ethanol–water solution will catch fire if heated above

6580-621: The compound C 2 H 5 −O− C 2 H 5 (commonly called "ether" in English , more specifically called " diethyl ether "). According to the Oxford English Dictionary , Ethyl is a contraction of the Ancient Greek αἰθήρ ( aithḗr , "upper air") and the Greek word ὕλη ( hýlē , "wood, raw material", hence "matter, substance"). Ethanol was coined as a result of

6674-536: The conversion: Fermentation is the process of culturing yeast under favorable thermal conditions to produce alcohol. This process is carried out at around 35–40 °C (95–104 °F). Toxicity of ethanol to yeast limits the ethanol concentration obtainable by brewing; higher concentrations, therefore, are obtained by fortification or distillation . The most ethanol-tolerant yeast strains can survive up to approximately 18% ethanol by volume. IUPAC nomenclature of organic chemistry In chemical nomenclature ,

6768-447: The end of a chain: CHOCH 2 COOH is 3-oxopropanoic acid. If the carbon in the carbonyl group cannot be included in the attached chain (for instance in the case of cyclic aldehydes ), the prefix "formyl-" or the suffix "-carbaldehyde" is used: C 6 H 11 CHO is cyclohexanecarbaldehyde. If an aldehyde is attached to a benzene and is the main functional group, the suffix becomes benzaldehyde. In general ketones ( R 2 C=O ) take

6862-414: The ethanol molecule also has a nonpolar end, it will also dissolve nonpolar substances, including most essential oils and numerous flavoring, coloring, and medicinal agents. The addition of even a few percent of ethanol to water sharply reduces the surface tension of water. This property partially explains the " tears of wine " phenomenon. When wine is swirled in a glass, ethanol evaporates quickly from

6956-429: The exhaled breath of healthy volunteers. Auto-brewery syndrome , also known as gut fermentation syndrome, is a rare medical condition in which intoxicating quantities of ethanol are produced through endogenous fermentation within the digestive system . Ethanol is produced both as a petrochemical , through the hydration of ethylene and, via biological processes, by fermenting sugars with yeast . Which process

7050-465: The figure above. If the alkyl group is not attached at the end of the chain, the bond position to the ester group is suffixed before "-yl": CH 3 CH 2 CH(CH 3 )OOCCH 2 CH 3 may be called butan-2-yl propanoate or butan-2-yl propionate. . The prefix form is "oxycarbonyl-" with the (R') group preceding. Acyl groups are named by stripping the "-ic acid" of the corresponding carboxylic acid and replacing it with "-yl." For example, CH 3 CO−R

7144-406: The laboratory by converting carbon dioxide via biological and electrochemical reactions. Ethanol can be produced from petrochemical feed stocks, primarily by the acid - catalyzed hydration of ethylene. It is often referred to as synthetic ethanol. The catalyst is most commonly phosphoric acid , adsorbed onto a porous support such as silica gel or diatomaceous earth . This catalyst

7238-450: The main constituent of B-Stoff . Under such nomenclature, the ethanol was mixed with 25% water to reduce the combustion chamber temperature. The V-2's design team helped develop U.S. rockets following World War II, including the ethanol-fueled Redstone rocket , which launched the first U.S. astronaut on suborbital spaceflight . Alcohols fell into general disuse as more energy-dense rocket fuels were developed, although ethanol

7332-440: The methyl group could not possibly occur on any of the other carbon atoms (that would lengthen the chain and result in butane, not propane) and therefore the use of the number "2" is unnecessary. If there is ambiguity in the position of the substituent, depending on which end of the alkane chain is counted as "1", then numbering is chosen so that the smaller number is used. For example, (CH 3 ) 2 CHCH 2 CH 3 (isopentane)

7426-512: The microbe's membrane. Ethanol can also be used as a disinfectant and antiseptic by inducing cell dehydration through disruption of the osmotic balance across the cell membrane, causing water to leave the cell, leading to cell death. Ethanol may be administered as an antidote to ethylene glycol poisoning and methanol poisoning . It does so by acting as a competitive inhibitor against methanol and ethylene glycol for alcohol dehydrogenase (ADH). Though it has more side effects, ethanol

7520-410: The name of the side-chain. If there are two side-chains with the same alpha carbon , the number will be written twice. Example: 2,2,3-trimethyl- . If there are both double bonds and triple bonds, "en" (double bond) is written before "yne" (triple bond). When the main functional group is a terminal functional group (a group which can exist only at the end of a chain, like formyl and carboxyl groups), there

7614-409: The number of carbons increases. The miscibility of ethanol with alkanes is limited to alkanes up to undecane : mixtures with dodecane and higher alkanes show a miscibility gap below a certain temperature (about 13 °C for dodecane ). The miscibility gap tends to get wider with higher alkanes, and the temperature for complete miscibility increases. Ethanol-water mixtures have less volume than

7708-416: The other chain is prefixed as an alkyl group with location prefix given as an italic N : CH 3 NHCH 2 CH 3 is N -methylethanamine. Tertiary amines ( R−NR−R ) are treated similarly: CH 3 CH 2 N(CH 3 )CH 2 CH 2 CH 3 is N -ethyl- N -methylpropanamine. Again, the substituent groups are ordered alphabetically. Amides ( R−C(=O)NH 2 ) take the suffix "-amide", or "-carboxamide" if

7802-532: The oxygen is not attached to the end of the main alkane chain, then the whole shorter alkyl-plus-ether group is treated as a side-chain and prefixed with its bonding position on the main chain. Thus CH 3 OCH(CH 3 ) 2 is 2-methoxypropane. Alternatively, an ether chain can be named as an alkane in which one carbon is replaced by an oxygen, a replacement denoted by the prefix "oxa". For example, CH 3 OCH 2 CH 3 could also be called 2-oxabutane, and an epoxide could be called oxacyclopropane. This method

7896-608: The plant from Otto Reider in 1992. He remains the Master Blender to this day. Forty Creek Barrel Select is a blended Canadian whisky, 40% alcohol ( ethanol ) by volume, 80 proof . It is made with rye, barley and corn ( maize ). Each grain is fermented, distilled, and aged separately to produce a "meritage" of single grain whiskies. After distillation using a small-batch, copper pot still , the whiskies are aged separately 6–10 years in small cask 40-gallon white oak barrels of varying toasting levels. Vintage sherry casks round off some of

7990-580: The prefix "cyclo alkyl -" (e.g. "cyclohexyl-") or for benzene, "phenyl-". The IUPAC nomenclature scheme becomes rapidly more elaborate for more complex cyclic structures, with notation for compounds containing conjoined rings, and many common names such as phenol being accepted as base names for compounds derived from them. When compounds contain more than one functional group, the order of precedence determines which groups are named with prefix or suffix forms. The table below shows common groups in decreasing order of precedence. The highest-precedence group takes

8084-420: The suffix " -one " (pronounced own , not won ) with a suffixed position number: CH 3 CH 2 CH 2 COCH 3 is pentan-2-one. If a higher precedence suffix is in use, the prefix "oxo-" is used: CH 3 CH 2 CH 2 COCH 2 CHO is 3-oxohexanal. In general, carboxylic acids ( R−C(=O)OH ) are named with the suffix -oic acid (etymologically a back-formation from benzoic acid ). As with aldehydes,

8178-601: The suffix, with all others taking the prefix form. However, double and triple bonds only take suffix form (-en and -yn) and are used with other suffixes. Prefixed substituents are ordered alphabetically (excluding any modifiers such as di-, tri-, etc.), e.g. chlorofluoromethane, not fluorochloromethane. If there are multiple functional groups of the same type, either prefixed or suffixed, the position numbers are ordered numerically (thus ethane-1,2-diol, not ethane-2,1-diol.) The N position indicator for amines and amides comes before "1", e.g., CH 3 CH(CH 3 )CH 2 NH(CH 3 )

8272-679: The sum of their individual components at the given fractions. Mixing equal volumes of ethanol and water results in only 1.92 volumes of mixture. Mixing ethanol and water is exothermic , with up to 777 J/mol being released at 298 K. Hydrogen bonding causes pure ethanol to be hygroscopic to the extent that it readily absorbs water from the air. The polar nature of the hydroxyl group causes ethanol to dissolve many ionic compounds, notably sodium and potassium hydroxides , magnesium chloride , calcium chloride , ammonium chloride , ammonium bromide , and sodium bromide . Sodium and potassium chlorides are slightly soluble in ethanol. Because

8366-542: The symptoms typically associated with alcohol intoxication—as well as many of the health hazards typically associated with the long-term consumption of ethanol—can be attributed to acetaldehyde toxicity in humans. The subsequent oxidation of acetaldehyde into acetate is performed by aldehyde dehydrogenase (ALDH) enzymes. A mutation in the ALDH2 gene that encodes for an inactive or dysfunctional form of this enzyme affects roughly 50 % of east Asian populations, contributing to

8460-449: The thin film of wine on the wall of the glass. As the wine's ethanol content decreases, its surface tension increases and the thin film "beads up" and runs down the glass in channels rather than as a smooth sheet. At atmospheric pressure, mixtures of ethanol and water form an azeotrope at about 89.4  mol% ethanol (95.6% ethanol by mass, 97% alcohol by volume ), with a boiling point of 351.3 K (78.1 °C). At lower pressure,

8554-422: The usual cation -then- anion conventions used for ionic compounds in both IUPAC and common nomenclature systems. The name of the carboxylate anion ( R−C(=O)O ) is derived from that of the parent acid by replacing the "–oic acid" ending with "–oate" or "carboxylate." For example, NaC 6 H 5 CO 2 , the sodium salt of benzoic acid ( C 6 H 5 COOH ), is called sodium benzoate. Where an acid has both

8648-448: The word acid is replaced with the word anhydride and the IUPAC name consists of two words. If the acyl groups are different, then they are named in alphabetical order in the same way, with anhydride replacing acid and IUPAC name consists of three words. For example, CH 3 CO−O−OCCH 3 is called ethanoic anhydride and CH 3 CO−O−OCCH 2 CH 3 is called ethanoic propanoic anhydride . Amines ( R−NH 2 ) are named for

8742-500: Was deemed Best Distiller . 43°12′9″N 79°34′59″W  /  43.20250°N 79.58306°W  / 43.20250; -79.58306  ( Forty Creek ) Ethanol Ethanol (also called ethyl alcohol , grain alcohol , drinking alcohol , or simply alcohol ) is an organic compound with the chemical formula CH 3 CH 2 OH . It is an alcohol , with its formula also written as C 2 H 5 OH , C 2 H 6 O or EtOH, where Et stands for ethyl . Ethanol

8836-506: Was first used for large-scale ethanol production by the Shell Oil Company in 1947. The reaction is carried out in the presence of high pressure steam at 300 °C (572 °F) where a 5:3 ethylene to steam ratio is maintained. This process was used on an industrial scale by Union Carbide Corporation and others. It is no longer practiced in the US as fermentation ethanol produced from corn

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