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16-September-2008 16:20:32 - Functional group For other uses, see Functional group disambiguation. Benzyl acetate has an ester functional group in red, an acetyl moiety circled with green and an benzyl alcohol moiety circled with orange. Benzyl acetate has an ester functional group in red, an acetyl moiety circled with green and an benzyl alcohol moiety circled with orange. In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. The same functional group will undergo the same or similar chemical reactions regardless of the size of the molecule it is a part of.12 However, its relative reactivity can be modified by nearby functional groups. The word moiety is often used synonymously to functional group, but according to the IUPAC definition, a moiety is a half of a molecule including substructures of functional groups. For example, an ester is divided into an alcohol and an acyl moiety, but has an ester functional group. The use of the word moiety to mean a functional group in the chemistry sense is actually fairly recent. While it has commonly been used in the archeology field to mean the half of a tribal family, it wasn't until a chance encounter between Elizabeth Bollwerk, an archeology graduate student, and a drug research scientist that the term made the cross-over.3 Combining the names of functional groups with the names of the parent alkanes generates a powerful systematic nomenclature for naming organic compounds. The non-hydrogen atoms of functional groups are always associated with each other and with the rest of the molecule by covalent bonds. When the group of atoms is associated with the rest of the molecule primarily by ionic forces, the group is referred to more properly as a polyatomic ion or complex ion. And all of these are called radicals, by a meaning of the term radical that predates the free radical. The first carbon atom after the carbon that attaches to the functional group is called the alpha carbon; the second, beta carbon, the third, gamma carbon, etc. If there is another functional group at a carbon, it may be named with the Greek letter, e.g. the gamma-amine in gamma-aminobutanoic acid is on the third carbon of the carbon chain attached to the carboxylic acid group. Functional groups are attached to the carbon backbone of organic molecules. They determine the characteristics and chemical reactivity of molecules. Functional groups are far less stable than the carbon backbone and are likely to participate in chemical reactions. Contents 1 Table of common functional groups 1.1 Hydrocarbons 1.2 Groups containing halogens 1.3 Groups containing oxygen 1.4 Groups containing nitrogen 1.5 Groups containing phosphorus and sulfur 1.6 Other 1.7 References 1.8 External links Table of common functional groups The following is a list of common functional groups. In the formulas, the symbols R and R' usually denote an attached hydrogen, or a hydrocarbon side chain of any length, but may sometimes refer to any group of atoms. Hydrocarbons Functional groups that vary based upon the number and order of Ï€ bonds impart different chemistry. Each listing below contains C-H bonds, but each one differs in type and scope of reactivity. Chemical class Group Formula Structural Formula Prefix Suffix Example Alkane Alkyl RH Alkyl alkyl- -ane methane Ethane Alkene Alkenyl R2C=CR2 Alkene alkenyl- -ene ethylene Ethylene Ethene Alkyne Alkynyl RC≡CR' Alkyne alkynyl- -yne acetylene Acetylene Ethyne Benzene derivative Phenyl RC6H5 RPh Phenyl phenyl- -benzene Cumene Cumene 2-phenylpropane Toluene derivative Benzyl RCH2C6H5 RBn Benzyl benzyl- 1-substituenttoluene Benzyl bromide Benzyl bromide 1-Bromotoluene There are also a large number of branched or ring alkanes that have specific names, e.g. tert-butyl, bornyl, cyclohexyl, etc. Groups containing halogens Haloalkanes are a class of molecule that is defined by a carbon-halogen bond. This bond can be relatively weak in the case of an iodoalkane or quite stable as in the case of a fluoroalkane. In general, with the exception of fluorinated compounds, haloalkanes readily undergo nucleophilic substitution reactions or elimination reactions. The substitution on the carbon, the acidity of an adjacent proton, the solvent conditions, etc. all can influence the outcome of the reactivity. Chemical class Group Formula Structural Formula Prefix Suffix Example haloalkane halo RX Halide group halo- alkyl halide Chloroethane Chloroethane Ethyl chloride fluoroalkane fluoro RF Fluoro group fluoro- alkyl fluoride Fluoromethane Fluoromethane Methyl fluoride chloroalkane chloro RCl Chloro group chloro- alkyl chloride Chloromethane Chloromethane Methyl chloride bromoalkane bromo RBr Bromo group bromo- alkyl bromide Bromomethane Bromomethane Methyl bromide iodoalkane iodo RI Iodo group iodo- alkyl iodide Iodomethane Iodomethane Methyl iodide Groups containing oxygen Compounds that contain C-O bonds each possess differing reactivity based upon the location and hybridization of the C-O bond, owing to the electron-withdrawing effect of sp² hybridized oxygen and the donating effects of sp³ hybridized oxygen. Chemical class Group Formula Structural Formula Prefix Suffix Example Acyl halide Haloformyl RCOX Acyl halide haloformyl- -oyl halide Acetyl chloride Acetyl chloride Ethanoyl chloride Alcohol Hydroxyl ROH Hydroxyl hydroxy- -ol methanol Methanol Ketone Carbonyl RCOR' Ketone keto-, oxo- -one Butanone Methyl ethyl ketone Butanone Aldehyde Aldehyde RCHO Aldehyde aldo- -al acetaldehyde Acetaldehyde Ethanal Carbonate Carbonate ester ROCOOR Carbonate alkyl carbonate Carboxylate Carboxylate RCOO- Carboxylate Carboxylate carboxy- -oate Sodium acetate Sodium acetate Sodium ethanoate Carboxylic acid Carboxyl RCOOH Carboxylic acid carboxy- -oic acid Acetic acid Acetic acid Ethanoic acid Ether Ether ROR' Ether alkoxy- alkyl alkyl ether Diethyl ether Diethyl ether Ethoxyethane Ester Ester RCOOR' Ester alkyl alkanoate Ethyl butyrate Ethyl butyrate Ethyl butanoate Hydroperoxide Hydroperoxy ROOH Hydroperoxy hydroperoxy- alkyl hydroperoxide Methyl ethyl ketone peroxide Methyl ethyl ketone peroxide Peroxide Peroxy ROOR Peroxy peroxy- alkyl peroxide Di-tert-butyl peroxide Di-tert-butyl peroxide Groups containing nitrogen Compounds that contain Nitrogen in this category may contain C-O bonds, such as in the case of amides. Chemical class Group Formula Structural Formula Prefix Suffix Example Amide Carboxamide RCONR2 Amide carboxamido- -amide acetamide Acetamide Ethanamide Amines Primary amine RNH2 Primary amine amino- -amine methylamine Methylamine Methanamine Secondary amine R2NH Secondary amine amino- -amine dimethylamine Dimethylamine Tertiary amine R3N Tertiary amine amino- -amine trimethylamine Trimethylamine 4° ammonium ion R4N+ Quaternary ammonium cation ammonio- -ammonium choline Choline Imine Primary ketimine RC=NHR' Imine imino- -imine Secondary ketimine RC=NRR' Imine imino- -imine Primary aldimine RC=NHH Imine imino- -imine Secondary aldimine RC=NR'H Imine imino- -imine Imide Imide RC=ONC=OR' Imide imido- -imide Azide Azide RN3 Organoazide azido- alkyl azide Phenyl azide Phenyl azide Azidobenzene Azo compound Azo Diimide RN2R' Azo.pngl azo- -diazene Methyl orange Methyl orange p-dimethylamino-azobenzenesulfonic acid Cyanates Cyanate ROCN Cyanate cyanato- alkyl cyanate Methyl cyanate Isocyanide RNC Isocyanide isocyano- alkyl isocyanide Isocyanates Isocyanate RNCO Isocyanate isocyanato- alkyl isocyanate Methyl isocyanate Methyl isocyanate Isothiocyanate RNCS Isothiocyanate isothiocyanato- alkyl isothiocyanate Allyl isothiocyanate Allyl isothiocyanate Nitrate Nitrate RONO2 Nitrate nitrooxy-, nitroxy- alkyl nitrate Amyl nitrate Amyl nitrate 1-nitrooxypentane Nitrile Nitrile RCN Nitrile cyano- alkanenitrile alkyl cyanide Benzonitrile Benzonitrile Phenyl cyanide Nitrite Nitrosooxy RONO Nitrite nitrosooxy- alkyl nitrite Amyl nitrite Isoamyl nitrite 3-methyl-1-nitrosooxybutane Nitro compound Nitro RNO2 Nitro nitro- Nitromethane Nitromethane Nitroso compound Nitroso RNO Nitroso nitroso- Nitrosobenzene Nitrosobenzene Pyridine derivative Pyridyl RC5H4N 4-pyridyl group 3-pyridyl group 2-pyridyl group 4-pyridyl pyridin-4-yl 3-pyridyl pyridin-3-yl 2-pyridyl pyridin-2-yl -pyridine Nicotine Nicotine Groups containing phosphorus and sulfur Compounds that contain sulfur and phosphorus exhibit unique chemistry due to their ability to form more bonds than nitrogen and oxygen, their lighter analogues on the periodic table. Chemical class Group Formula Structural Formula Prefix Suffix Example Phosphine Phosphino R3P A tertiary phosphine phosphino- -phosphane Methylpropylphosphane Methylpropylphosphane Phosphodiester Phosphate HOPOOR2 Phosphodiester phosphoric acid disubstituent ester disubstituent hydrogenphosphate DNA Phosphonic acid Phosphono RP=OOH2 Phosphono group phosphono- substituent phosphonic acid Benzylphosphonic acid Benzylphosphonic acid Phosphate Phosphate ROP=OOH2 Phosphate group phospho- Glyceraldehyde 3-phosphate Glyceraldehyde 3-phosphate Sulfide or thioether RSR' Sulfide group disubstituent sulfide Dimethyl sulfide Dimethyl sulfide Sulfone Sulfonyl RSO2R' Sulfonyl group sulfonyl- disubstituent sulfone Dimethyl sulfone Dimethyl sulfone Methylsulfonylmethane Sulfonic acid Sulfo RSO3H Sulfonyl group sulfo- substituent sulfonic acid Benzenesulfonic acid Benzenesulfonic acid Sulfoxide Sulfinyl RSOR' Sulfinyl group sulfinyl- disubstituent sulfoxide Diphenyl sulfoxide Diphenyl sulfoxide Thiol Sulfhydryl RSH Sulfhydryl mercapto-, sulfanyl- -thiol Ethanethiol Ethanethiol Ethyl mercaptan Thiocyanate Thiocyanate RSCN Thiocyanate thiocyanato- alkyl thiocyanate Disulfide Disulfide RSSR' Disulfide alkyl alkyl disulfide Diphenyl disulfide Diphenyl disulfide 1,2-diphenyldisulfane Other For a list of all functional groups: Category:Functional groups References ^ Compendium of Chemical Terminology IUPAC Gold Book http://goldbook.iupac.org/F02555.html ^ March, Jerry 1985. Advanced Organic Chemistry, Reactions, Mechanisms and Structure, third ion, John Wiley Sons. ISBN 0-471-85472-7. ^ Schleselmann, L. 2004, Pharmacy Times, Pharmacological History Notes, http://www.pharmacytimes.com/issues/articles/2004-06_121.asp accessed 5/1/08 External links IUPAC Blue Book organic nomenclature IUPAC ligand abbreviations pdf Organic Chemistry Help: Functional Groups Flashcards v d e Functional groups Chemical class: Alcohol Aldehyde Alkane Alkene Alkyne Amide Amine Azo compound Benzene derivative Carboxylic acid Cyanate Disulfide Ester Ether Haloalkane Hydrazone Imine Isocyanide Isocyanate Ketone Oxime Nitrile Nitro compound Nitroso compound Peroxide Phosphoric acid Pyridine derivative Sulfone Sulfonic acid Sulfoxide Thioester Thioether Thiol v d e Concepts in organic chemistry Aromaticity, Covalent bonding, Functional groups, Nomenclature, Organic compounds, Organic reactions, Organic synthesis, Publications, Spectroscopy, Stereochemistry, List of organic compounds Retrieved from http://en..org/wiki/Functional_group Categories: Functional groups | Organic compounds Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages العربية Bosanski Català Česky Dansk Deutsch Eesti Ελληνικά Español Esperanto Ù?ارسی Français í•œêµì–´ Bahasa Indonesia Italiano עברית МакедонÑ?ки Bahasa Melayu Nederlands 日本語 ‪Norsk bokmÃ¥l‬ ‪Norsk nynorsk‬ Occitan Polski Português Română РуÑ?Ñ?кий SlovenÄ?ina Suomi Svenska ไทย Tiếng Việt Türkçe УкраїнÑ?ька ä¸æ–‡ This page was last modified on 8 August 2008, at 08:06
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