Functional groups - Biblioteka.sk

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Functional groups
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Example functional groups of benzyl acetate:
  Ester group
  Acetyl group
  Benzyloxy group

In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest of the molecule's composition.[1][2] This enables systematic prediction of chemical reactions and behavior of chemical compounds and the design of chemical synthesis. The reactivity of a functional group can be modified by other functional groups nearby. Functional group interconversion can be used in retrosynthetic analysis to plan organic synthesis.

A functional group is a group of atoms in a molecule with distinctive chemical properties, regardless of the other atoms in the molecule. The atoms in a functional group are linked to each other and to the rest of the molecule by covalent bonds. For repeating units of polymers, functional groups attach to their nonpolar core of carbon atoms and thus add chemical character to carbon chains. Functional groups can also be charged, e.g. in carboxylate salts (−COO), which turns the molecule into a polyatomic ion or a complex ion. Functional groups binding to a central atom in a coordination complex are called ligands. Complexation and solvation are also caused by specific interactions of functional groups. In the common rule of thumb "like dissolves like", it is the shared or mutually well-interacting functional groups which give rise to solubility. For example, sugar dissolves in water because both share the hydroxyl functional group (−OH) and hydroxyls interact strongly with each other. Plus, when functional groups are more electronegative than atoms they attach to, the functional groups will become polar, and the otherwise nonpolar molecules containing these functional groups become polar and so become soluble in some aqueous environment.

Combining the names of functional groups with the names of the parent alkanes generates what is termed a systematic nomenclature for naming organic compounds. In traditional nomenclature, 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-aminobutyric acid is on the third carbon of the carbon chain attached to the carboxylic acid group. IUPAC conventions call for numeric labeling of the position, e.g. 4-aminobutanoic acid. In traditional names various qualifiers are used to label isomers, for example, isopropanol (IUPAC name: propan-2-ol) is an isomer of n-propanol (propan-1-ol). The term moiety has some overlap with the term "functional group". However, a moiety is an entire "half" of a molecule, which can be not only a single functional group, but also a larger unit consisting of multiple functional groups. For example, an "aryl moiety" may be any group containing an aromatic ring, regardless of how many functional groups the said aryl has.

Table of common functional groups

The following is a list of common functional groups.[3] 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

Hydrocarbons are a class of molecule that is defined by functional groups called hydrocarbyls that contain only carbon and hydrogen, but vary in the number and order of double bonds. Each one differs in type (and scope) of reactivity.

Chemical class Group Formula Structural Formula Prefix Suffix Example
Alkane Alkyl R(CH2)nH Alkyl alkyl- -ane
Ethane
Alkene Alkenyl R2C=CR2 Alkene alkenyl- -ene ethylene
Ethylene
(Ethene)
Alkyne Alkynyl RC≡CR' alkynyl- -yne
Acetylene
(Ethyne)
Benzene derivative Phenyl RC6H5
RPh
Phenyl phenyl- -benzene
Cumene
(Isopropylbenzene)

There are also a large number of branched or ring alkanes that have specific names, e.g., tert-butyl, bornyl, cyclohexyl, etc. Hydrocarbons may form charged structures: positively charged carbocations or negative carbanions. Carbocations are often named -um. Examples are tropylium and triphenylmethyl cations and the cyclopentadienyl anion.

Groups containing halogen

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 halo- alkyl halide
Chloroethane
(Ethyl chloride)
fluoroalkane fluoro RF fluoro- alkyl fluoride
Fluoromethane
(Methyl fluoride)
chloroalkane chloro RCl chloro- alkyl chloride Chloromethane
Chloromethane
(Methyl chloride)
bromoalkane bromo RBr bromo- alkyl bromide
Bromomethane
(Methyl bromide)
iodoalkane iodo RI 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 sp-hybridized oxygen (carbonyl groups) and the donating effects of sp2-hybridized oxygen (alcohol groups).

Chemical class Group Formula Structural formula Prefix Suffix Example
Alcohol Hydroxyl ROH
Hydroxyl
Hydroxyl
hydroxy- -ol methanol
Methanol
Ketone Ketone RCOR' Ketone -oyl- (-COR')
or
oxo- (=O)
-one Butanone
Butanone
(Methyl ethyl ketone)
Aldehyde Aldehyde RCHO Aldehyde formyl- (-COH)
or
oxo- (=O)
-al acetaldehyde
Acetaldehyde
(Ethanal)
Acyl halide Haloformyl RCOX Acyl halide carbonofluoridoyl-
carbonochloridoyl-
carbonobromidoyl-
carbonoiodidoyl-
-oyl fluoride
-oyl chloride
-oyl bromide
-oyl iodide
Acetyl chloride
Acetyl chloride
(Ethanoyl chloride)
Carbonate Carbonate ester ROCOOR' Carbonate (alkoxycarbonyl)oxy- alkyl carbonate triphosgene
Triphosgene
(bis(trichloromethyl) carbonate)
Carboxylate Carboxylate RCOO
Carboxylate
Carboxylate

Carboxylate
carboxylato- -oate Sodium acetate
Sodium acetate
(Sodium ethanoate)
Carboxylic acid Carboxyl RCOOH Carboxylic acid carboxy- -oic acid Acetic acid
Acetic acid
(Ethanoic acid)
Ester Carboalkoxy RCOOR' Ester alkanoyloxy-
or
alkoxycarbonyl
alkyl alkanoate Ethyl butyrate
Ethyl butyrate
(Ethyl butanoate)
Hydroperoxide Hydroperoxy ROOH Hydroperoxy hydroperoxy- alkyl hydroperoxide tert-Butyl hydroperoxide
tert-Butyl hydroperoxide
Peroxide Peroxy ROOR' Peroxy peroxy- alkyl peroxide Di-tert-butyl peroxide
Di-tert-butyl peroxide
Ether Ether ROR'
Ether
Ether
alkoxy- alkyl ether Diethyl ether
Diethyl ether
(Ethoxyethane)
Hemiacetal Hemiacetal R2CH(OR1)(OH) Hemiacetal alkoxy -ol -al alkyl hemiacetal
Hemiketal Hemiketal RC(ORʺ)(OH)R' Hemiketal alkoxy -ol -one alkyl hemiketal
Acetal Acetal RCH(OR')(OR") Acetal dialkoxy- -al dialkyl acetal
Ketal (or Acetal) Ketal (or Acetal) RC(OR")(OR‴)R' Ketal dialkoxy- -one dialkyl ketal
Orthoester Orthoester RC(OR')(OR")(OR‴) Orthoester trialkoxy-
Heterocycle
(if cyclic)
Methylenedioxy (–OCH2O–)

methylenedioxy- -dioxole
1,2-Methylenedioxybenzene
(1,3-Benzodioxole)
Orthocarbonate ester Orthocarbonate ester C(OR)(OR')(OR")(OR‴) Orthocarbonate ester tetralkoxy- tetraalkyl orthocarbonate
Tetramethoxymethane
Organic acid anhydride Carboxylic anhydride R1(CO)O(CO)R2 Carboxylic anhydride anhydride Butyric anhydride
Butyric anhydride

Groups containing nitrogen

Compounds that contain nitrogen in this category may contain C-O bonds, such as in the case of amides.

Zdroj:https://en.wikipedia.org?pojem=Functional_groups
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Chemical class Group Formula Structural formula Prefix Suffix Example
Amide Carboxamide RCONR'R" Amide carboxamido-
or
carbamoyl-
-amide acetamide
Acetamide
(Ethanamide)
Amidine Amidine RC(NR)NR2 amidino- -amidine acetamidine

(acetimidamide)

Amines Primary amine RNH2 Primary amine amino- -amine methylamine
Methylamine
(Methanamine)
Secondary amine R'R"NH 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
Hydrazone R'R"CN2H2
hydrazino- -hydrazine
Benzophenone
Imine Primary ketimine RC(=NH)R' Imine imino- -imine
Secondary ketimine Imine imino- -imine