A functional group is an atom or group of atoms that determines the chemical properties of an organic compound. Common functional groups include hydroxyl, carboxyl, ether, aldehyde, carbonyl, and the like. Organic chemical reactions mainly occur on functional groups, and functional groups play a decisive role in the properties of organic substances. -X (X is a halogen atom. For halogenated hydrocarbons, the halogen atom can be considered as its functional group, but some textbooks think that the carbon-halogen bond is its functional groups), -OH, -CHO, -COOH, -NO2, -SO3H, -NH2, RCO-, these functional groups determine the halogenated hydrocarbons, alcohols or phenols, aldehydes, carboxylic acids, nitro compounds or Chemical properties of nitrites, sulfonic acid organics, amines, amides.
Resulting in heterogeneity
The classification of organics is based on composition, carbon chain, functional groups and homologues.
There are three types of isomerism in organic matter: carbon chain isomerism, functional group positional isomerism and functional group isomerism. For similar organic compounds, the isomerism caused by the different positions of functional groups is the positional isomerism of functional groups. For example, the following 8 isomers of vinyl chloride reflect the different positions of carbon-carbon double bonds and chlorine atoms. Heterogeneous.
For the same atomic composition, different functional groups are formed, thus forming different types of organic substances, which is the species isomerism of functional groups. For example, aldehydes and ketones with the same number of carbon atoms, carboxylic acids and esters with the same number of carbon atoms, are all different types of isomerism caused by the formation of different functional groups.
Chemical properties
Functional groups play a decisive role in the properties of organic matter, -X, -OH, -CHO, -COOH, -NO2, -SO3H, -NH2, RCO-, these functional groups determine the halogenated hydrocarbons, alcohols or phenols, aldehydes in organic matter , carboxylic acids, nitro compounds or nitrites, sulfonic acid organics, amines, amides chemical properties. Therefore, learning the properties of organic substances is actually learning the properties of functional groups. Organic substances containing any functional groups should have the chemical properties of such functional groups. Organic substances that do not contain such functional groups do not possess the chemical properties of such functional groups. A point to be aware of in particular in chemistry. For example, aldehydes can undergo silver mirror reaction or be oxidized by freshly prepared copper hydroxide suspension, which can be considered as a more characteristic reaction of aldehydes; but this is not unique to aldehydes, but to aldehyde groups Therefore, all substances containing aldehyde groups, such as glucose, formic acid and formate, can undergo silver mirror reaction, or be oxidized by newly prepared copper hydroxide suspension.
Other properties
There are interactions among groups in organic molecules, including the influence of functional groups on hydrocarbon groups, the influence of hydrocarbon groups on functional groups, and the interactions among functional groups in substances containing multiple functional groups.
① Alcohols, phenols and carboxylic acids contain hydroxyl groups in their molecules, so they can react with sodium to release hydrogen, but due to the different groups connected, there are differences in acidity.
R-OH is neutral and cannot react with NaOH and Na2CO3; the hydroxyl group directly connected to the benzene ring becomes a phenolic hydroxyl group, and the hydroxyl group not directly connected to the benzene ring becomes an alcoholic hydroxyl group.
C6H5-OH is very weakly acidic, weaker than carbonic acid, but stronger than HCO3-(bicarbonate). Can not make the indicator change color, can react with NaOH. Phenol can also react with sodium carbonate to generate sodium phenolate and sodium bicarbonate;
R-COOH is weakly acidic, has the property of acid, and can react with NaOH and Na2CO3.
Obviously, in carboxylic acids, the influence of the carbonyl group in the carboxyl group makes the hydrogen in the hydroxyl group easy to ionize.
② Both aldehydes and ketones have carbonyl groups (>C=O), but the carbonyl carbon atoms in aldehydes are connected to a hydrogen atom, and the carbonyl carbon atoms in ketones are connected to hydrocarbon groups, so the former has reducibility, and the latter is relatively stable, not weak oxidized by oxidants.
③ Atomic groups in the same molecule also affect each other. Like phenol, -OH makes the benzene ring easily substituted (activated), and phenyl makes -OH acidic (ie, ionizes H+). In fructose, the polyhydroxyl group affects the carbonyl group, and the silver mirror reaction can occur.
As can be seen from the above, we can not only determine the chemical properties of organic matter by the functional groups contained in the organic matter, but also judge the functional groups contained in it by the chemical properties of the substance. For example, glucose can undergo silver mirror reaction, hydrogenated and reduced to hexavalent alcohol, and it can be known that it has an aldehyde group; it can be esterified with acid to generate glucose pentaacetate, indicating that it has five hydroxyl groups, so it is a polyhydroxy aldehyde.
Organic chemistry reactions take place primarily on functional groups, so pay attention to what bonds the reactions take place on in order to write chemical equations correctly.
For example, the hydrogenation of aldehyde occurs on the carbon-oxygen bond of the aldehyde group, and the oxidation occurs on the carbon-hydrogen bond of the aldehyde group; the substitution of halogenated hydrocarbon occurs on the carbon-halogen bond, and the elimination of carbon occurs on the carbon-halogen bond and adjacent carbon atoms. On the hydrogen bond; the esterification of alcohol is the breaking of the O-H bond in the hydroxyl group, and the substitution is the breaking of the C-O bond; the addition polymerization is a carbon-carbon double bond (>C=C<) (not necessarily an olefin) The unique reaction of the compound is that during polymerization, the groups on the carbon of the double bond are thrown up and down, and one bond in the double bond is opened and connected hand in hand.
Hydrocarbyl
Different hydrocarbyl functional groups have different properties depending on the π bond they contain. Note: Alkyl groups (eg methyl, methylene) do not count as functional groups, while phenyl groups are.
Classification |
Functional group name |
Chemical formula |
Prefix |
Suffix |
---|---|---|---|---|
Alkanes |
Alkyl |
RH |
alkyl- |
-ane |
Olefins |
Alkenyl |
R2C=CR2 |
alkenyl- |
-ene |
Alkynes |
Alkynyl |
RC≡CR' |
alkynyl- |
-yne |
Benzene and Derivatives |
Phenyl |
RC6H5 RPh |
phenyl- |
-benzene |
Toluene and derivatives |
Benzyl |
RCH2C6H5 RBn |
benzyl- |
1-(substituent)toluene |
Halogen-containing substituents
Halogenated hydrocarbons contain carbon-halogen bonds, and the bond energy varies with different halogens. In addition to fluorohydrocarbons, halogenated hydrocarbons can undergo nucleophilic substitution and elimination reactions.
Classification |
Functional group name |
Chemical formula |
Prefix |
Suffix |
---|---|---|---|---|
Haloalkanes |
Carbon-halogen bond |
RX |
halo- |
alkylhalide |
Fluoroalkane |
Carbon-fluorine bond |
RF |
fluoro- |
alkylfluoride |
Chloroalkanes |
Carbon-chlorine bond |
RCl |
chloro- |
alkylchloride |
Bromoalkane |
Carbon bromine bond |
RBr |
bromo- |
alkylbromide |
Iodoalkane |
Carbon iodine bond |
RI |
iodo- |
alkyliodide |
Oxygenated
Different carbon-oxygen bonds have different properties due to the degree of atomic hybridization in them. The sp hybridized oxygen atom has electron withdrawing effect, while sp has electron donating effect.
Classification | Functional group name div> | Chemical formula | Prefix | Suffix |
---|---|---|---|---|
Acyl halides | Haloformyl | RCOX | haloformyl- | -oyl halide |
ol | hydroxy | ROH | hydroxy- | -ol |
ketone | carbonyl | RCOR' | keto-, oxo- | -one |
aldehyde | aldehyde group td> | RCHO | aldo- | -al |
Carbonate | Carbonate | ROCOOR | alkylcarbonate | |
carboxy acid | carboxylate | RCOO | carboxy- | -oate |
carboxylic acid | carboxy | RCOOH | carboxy- | -oic acid |
ether | ether | ROR' | alkoxy- | alkyl alkyl ether |
ester | ester | RCOOR' | alkyl alkanoate | |
Hydroperoxide | Hydroperoxide | ROOH | hydroperoxy- | alkylhydroperoxide |
Peroxide | Peroxy | ROOR | peroxy- | alkylperoxide |
Nitrogenous
Classification | functional group name | chemical formula | Prefix | Suffix | |
---|---|---|---|---|---|
Amide | Amide | RCONH2 | carboxamido- | -amide | |
amine | Primary Amine | RNH2 | amino- | -amine | |
Secondary amine | R2NH | amino- | -amine | ||
Tertiary amine | R3N | amino- | -amine | ||
quaternium Quaternary ammonium cations | R4N | ammonio- | -ammonium | ||
Imine | Primary Ketimine | RC(=NH)R' | imino- | -imine | |
Secondary Ketimine | RC(=NR)R ' | imino- | -imine | ||
Primary aldimine | RC(=NH)H | imino- | -imine | ||
Secondary aldimine | RC(=NR')H | imino- | -imine | ||
imine | imide | RC(=O)NC(=O)R' | imido- | -imide | |
azide | azide | RN3 | azido- | alkylazide | Azobenzene |
Azo Compounds | azo group | RN2R' | azo- | -diazene | methyl yellow |
cyanate | cyanate | ROCN | cyanato- | alkylcyanate | |
Isonitrile | RNC | isocyano- | alkylisocyanide | ||
Isocyanates | Isocyanates | RNCO | isocyanato- | alkyl isocyanate | methyl isocyanate |
isocyanurate Thiocyanate | RNCS | isothiocyanato- | alkylisothiocyanate | allyl isothiocyanate | |
Nitrates | Nitrates | RONO2 | nitrooxy-, nitroxy- | alkylnitrate | n-amyl nitrate |
cyano | RCN | cyano- | alkanenitrile alkylcyanide | Benzonitrile | |
Nitrite | Nitrite | RONO | nitrosooxy- | alkylnitrite | isoamyl nitrite |
Nitro Compounds | Nitro | RNO2 | nitro- | nitromethane | |
nitroso compounds | nitroso | RNO | nitroso- | Nitrosobenzene | |
pyridineand derivatives | pyridyl | RC5H4N | 4-pyridyl (pyridin-4-yl) 3-pyridyl (pyridin-3-yl) 2-pyridyl (pyridin-2-yl) | -pyridine | Nicotine |
Phosphorus-containing sulfur
Heteroatoms in organophosphorus and organosulfur compounds tend to form more bonds than their homogeneous groups of nitrogen and oxygen.
Classification | functional group name | chemical formula | Prefix | Suffix |
---|---|---|---|---|
phosphine | phosphine | R3P | phosphino- | -phosphane |
phosphodiester | phosphonates | HOPO(OR)2 | phosphoric acid di(substituent) ester | di(substituent) hydrogenphosphate |
phosphite | Phosphite | RP(=O)(OH)2 | phosphono- | substituentphosphonic acid |
Phosphate | Phosphate | ROP(=O )(OH)2 | phospho- | |
thioether | thioether | RSR' | di(substituent) sulfide | |
sulfone | sulfonyl | RSO2R' | sulfonyl- | di(substituent) sulfone |
sulfone | sulfonic acid | RSO3H | sulfo- | substituentsulfonic acid |
Sulfoxide | Sulfonyl | RSOR' | sulfinyl- | di(substituent)sulfoxide |
thiol | thiol | RSH | mercapto-, sulfanyl- | -thiol |
thiocyanate | thiocyanate | RSCN | thiocyanato- | alkylthiocyanate |
Disulfide | Disulfide | RSSR' | alkyl alkyl disulfide |