Intro Functional Groups Flashcards
Alcohol
A hydroxyl group is a hydrogen bonded to an oxygen that is covalently bonded to the rest of the molecule. Just as with alkenes, alkynes, and ketones, the location of the hydroxyl group is made by numbering the molecule such that the hydroxyl group has the lowest number possible. Alcohols are subdivided by examining the carbon to which the hydroxyl group is bonded. If this carbon is bonded to one other carbon atom, it is a primary (1°) alcohol. If this carbon is bonded to two other carbons, it is a secondary (2°) alcohol. If it is bonded to three other carbons, it is a tertiary (3°) alcohol.
Aldehyde
An organic compound containing a formyl group. The formyl group is a functional group, with the structure R-CHO, consisting of a carbonyl center (a carbon double bonded to oxygen) bonded to hydrogen and an R group, which is any generic alkyl or side chain. The group without R is called the aldehyde group or formyl group. Aldehydes differ from ketones in that the carbonyl is placed at the end of a carbon skeleton rather than between two carbon atoms. Many fragrances are aldehydes.
Alkane
An alkane, or paraffin (a still-used historical name that also has other meanings), is a saturated hydrocarbon. Alkanes consist only of hydrogen and carbon atoms and all bonds are single bonds. Alkanes (technically, always acyclic) have the general chemical formula CnH2n+2. Alkanes belong to a homologous series of organic compounds in which the members differ by a molecular mass of 14.03u (mass of a methanediyl group, —CH2—, one carbon atom of mass 12.01u, and two hydrogen atoms of mass ≈1.01u each). There are two main commercial sources: crude oil and natural gas.
Alkene
Aliphatic hydrocarbons with one double bond between carbons are called alkenes. They follow the naming convention of the alkanes except that the suffix -ene is used instead of -ane. For alkenes above propene the position of the double bond must be specified in the name. Alkenes are unsaturated hydrocarbons and are generally very reactive. Typical reactions involve the addition of hydrogens or halogens. The double bond in alkenes can act to bond such molecules together in long chains and sheets. The formation of polymers is an important area of chemistry.
Halide
A halide is a binary compound, of which one part is a halogen atom and the other part is an element or radical that is less electronegative (or more electropositive) than the halogen, to make a fluoride, chloride, bromide, iodide, or astatide compound. Many salts are halides; the hal-syllable in halide and halite reflects this correlation. All Group 1 metals form halides that are white solids at room temperature.
A halide ion is a halogen atom bearing a negative charge. The halide anions are fluoride (F−), chloride (Cl−), bromide (Br−), iodide (I−) and astatide (At−). Such ions are present in all ionic halide salts. Halide minerals contain halides.
Alkyne
An alkyne is an unsaturatedhydrocarbon which has at least one carbon—carbon triple bond between two carbon atoms. The simplest acyclic alkynes with only one triple bond and no other functional groups form a homologous series with the general chemical formula CnH2n-2. Alkynes are traditionally known as acetylenes, although the name acetylene also refers specifically to C2H2, known formally as ethyne using IUPAC nomenclature. Like other hydrocarbons, alkynes are generally hydrophobic but tend to be more reactive.
Amide
An amide, also known as an acid amide, is a compound with the functional group RnE(O)xNR’2 (R and R’ refer to H or organic groups). Most common are “organic amides” (n = 1, E = C, x = 1), but many other important types of amides are known including phosphor amides (n = 2, E = P, x = 1 and many related formulas) and sulfonamides (E = S, x= 2). The term amide refers both to classes of compounds and to the functional group (RnE(O)xNR’2) within those compounds.
Amine
Amines are organic compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines, trimethylamine, and aniline. Inorganic derivatives of ammonia are also called amines, such as chloramine (NClH2).
Compounds with the nitrogen atom attached to a carbonyl of the structure R–CO–NR′R″ are called amides and have different chemical properties from amines.
Benzene
Benzene is an organic chemical compound with the molecular formula C6H6. Its molecule is composed of 6 carbon atoms joined in a ring, with 1 hydrogen atom attached to each carbon atom. Because its molecules contain only carbon and hydrogen atoms, benzene is classed as a hydrocarbon. Removing one hydrogen and replacing it with another substituient produces a phenyl group.
Benzene is considered to be unsaturated because it has double carbon-carbon covalent bonds. These bonds are not restricted to specific carbons, but are de-localized due to the resonance caused by the circular structure of the molecule. The unique nature of benzene’s double bonding makes benzene act somewhat like a saturated hydrocarbon. It is slow to react or is un-reactive, in contradiction to what might otherwise be normal expectations.
Carboxylic Acid
A carboxylic acid is an organic compound that contains a carboxyl group (C(O)OH). The general formula of a carboxylic acid is R-C(O)OH with R referring to the rest of the (possibly quite large) molecule. Carboxylic acids occur widely, and include the amino acids and acetic acid (active ingredient in vinegar).
Salts and esters of carboxylic acids are called carboxylates. When a carboxyl group is deprotonated, its conjugate base forms a carboxylate anion. Carboxylate ions are resonance stabilized and this increased stability makes carboxylic acids more acidic than alcohols. Carboxylic acids can be seen as reduced or alkylated forms of the Lewis acid carbon dioxide; under some circumstances they can be decarboxylated to yield carbon dioxide.
Ester
Esters are usually derived from an inorganic acid or organic acid in which at least one -OH (hydroxyl) group is replaced by an -O-alkyl (alkoxy) group. Commonly esters are derived from carboxylic acids and alcohol. Esters comprise most naturally occurring fats and oils, which are fatty acidesters of glycerol. Esters with low molecular weight are commonly used as fragrances and found in essential oils and pheromones. Phosphoesters form the backbone of DNA molecules. Nitrate esters, such as nitroglycerin, are known for their explosive properties, while polyesters are important plastics, with monomers linked by ester moieties.
Ether
Ethers are a class of organic compounds that contain an ether group — an oxygen atom connected to two alkyl or aryl groups — of general formula R–O–R’. A typical example is the solvent and anesthetic diethyl ether, commonly referred to simply as “ether” (CH3-CH2-O-CH2-CH3). Ethers are common in organic chemistry and pervasive in biochemistry, as they are common linkages in carbohydrates and lignin.
Ketone
A ketone (or alkanone) is an organic compoundwith the structure RC(=O)R’, where R and R’ can be a variety of carbon-containing substituents. Ketones and Aldehydes are simple compounds that contain a carbonyl group (a carbon-oxygen double bond). They are considered “simple” because they don’t have reactive groups like -OH or -Cl attached directly to the carbon atom in the carbonyl group, as in carboxylic acids containing -COOH. Examples include many sugars (ketoses) and the industrial solvent acetone.
Phenol
Phenol, also known as carbolic acid, is an aromatic organic compound with the molecular formula C6H5OH. It is a white crystalline solid that is volatile. The molecule consists of a phenyl group (-C6H5) bonded to a hydroxyl group (-OH). It is mildly acidic, but requires careful handling due to its propensity to cause chemical burns.
Although similar to alcohols, phenols have unique distinguishing properties. Unlike in alcohols where the hydroxyl group is bound to a saturated carbon atom,in phenols the hydroxyl group is attached to an unsaturated aromatic (alternating double and single bond) hydrocarbon ring such as benzene. Consequently, phenols have greater acidity than alcohols due to stabilization of the conjugate base through resonance in the aromatic ring.
Aliphatic Hydrocarbon
Hydrocarbons which do not contain a benzene ring are called aliphatic hydrocarbons. Those which do contain benzine are called aromatic hydrocarbons.
Phenyl Group
In organic chemistry, the phenyl group or phenyl ring is a cyclicgroup of atoms with the formula C6H5. Phenyl groups are closely related to benzene. Phenyl groups have six carbon atoms bonded together in a hexagonal planar ring, five of which are bonded to individual hydrogen atoms, with the remaining carbon bonded to a substituent. Although often depicted with alternating double and single bonds, phenyl groups are chemically aromatic and show nearly equal bond lengths between carbon atoms in the ring.
What does the suffix -ane imply?
An alkane with no functional groups. Alkanes, both straight chained and branched, obey the formula CnH2n+2.
Alcohol
A hydroxyl group is a hydrogen bonded to an oxygen that is covalently bonded to the rest of the molecule. Just as with alkenes, alkynes, and ketones, the location of the hydroxyl group is made by numbering the molecule such that the hydroxyl group has the lowest number possible. Alcohols are subdivided by examining the carbon to which the hydroxyl group is bonded. If this carbon is bonded to one other carbon atom, it is a primary (1°) alcohol. If this carbon is bonded to two other carbons, it is a secondary (2°) alcohol. If it is bonded to three other carbons, it is a tertiary (3°) alcohol.
Aldehyde
An organic compound containing a formyl group. The formyl group is a functional group, with the structure R-CHO, consisting of a carbonyl center (a carbon double bonded to oxygen) bonded to hydrogen and an R group, which is any generic alkyl or side chain. The group without R is called the aldehyde group or formyl group. Aldehydes differ from ketones in that the carbonyl is placed at the end of a carbon skeleton rather than between two carbon atoms. Many fragrances are aldehydes.
Alkane
An alkane, or paraffin (a still-used historical name that also has other meanings), is a saturated hydrocarbon. Alkanes consist only of hydrogen and carbon atoms and all bonds are single bonds. Alkanes (technically, always acyclic) have the general chemical formula CnH2n+2. Alkanes belong to a homologous series of organic compounds in which the members differ by a molecular mass of 14.03u (mass of a methanediyl group, —CH2—, one carbon atom of mass 12.01u, and two hydrogen atoms of mass ≈1.01u each). There are two main commercial sources: crude oil and natural gas.
Alkene
Aliphatic hydrocarbons with one double bond between carbons are called alkenes. They follow the naming convention of the alkanes except that the suffix -ene is used instead of -ane. For alkenes above propene the position of the double bond must be specified in the name. Alkenes are unsaturated hydrocarbons and are generally very reactive. Typical reactions involve the addition of hydrogens or halogens. The double bond in alkenes can act to bond such molecules together in long chains and sheets. The formation of polymers is an important area of chemistry.
Halide
A halide is a binary compound, of which one part is a halogen atom and the other part is an element or radical that is less electronegative (or more electropositive) than the halogen, to make a fluoride, chloride, bromide, iodide, or astatide compound. Many salts are halides; the hal-syllable in halide and halite reflects this correlation. All Group 1 metals form halides that are white solids at room temperature.
A halide ion is a halogen atom bearing a negative charge. The halide anions are fluoride (F−), chloride (Cl−), bromide (Br−), iodide (I−) and astatide (At−). Such ions are present in all ionic halide salts. Halide minerals contain halides.
Alkyne
An alkyne is an unsaturatedhydrocarbon which has at least one carbon—carbon triple bond between two carbon atoms. The simplest acyclic alkynes with only one triple bond and no other functional groups form a homologous series with the general chemical formula CnH2n-2. Alkynes are traditionally known as acetylenes, although the name acetylene also refers specifically to C2H2, known formally as ethyne using IUPAC nomenclature. Like other hydrocarbons, alkynes are generally hydrophobic but tend to be more reactive.
Amide
An amide, also known as an acid amide, is a compound with the functional group RnE(O)xNR’2 (R and R’ refer to H or organic groups). Most common are “organic amides” (n = 1, E = C, x = 1), but many other important types of amides are known including phosphor amides (n = 2, E = P, x = 1 and many related formulas) and sulfonamides (E = S, x= 2).[1] The term amide refers both to classes of compounds and to the functional group (RnE(O)xNR’2) within those compounds.
Amine
Amines are organic compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines, trimethylamine, and aniline. Inorganic derivatives of ammonia are also called amines, such as chloramine (NClH2).
Compounds with the nitrogen atom attached to a carbonyl of the structure R–CO–NR′R″ are called amides and have different chemical properties from amines.
Benzene
Benzene is an organic chemical compound with the molecular formula C6H6. Its molecule is composed of 6 carbon atoms joined in a ring, with 1 hydrogen atom attached to each carbon atom. Because its molecules contain only carbon and hydrogen atoms, benzene is classed as a hydrocarbon. Removing one hydrogen and replacing it with another substituient produces a phenyl group.
Benzene is considered to be unsaturated because it has double carbon-carbon covalent bonds. These bonds are not restricted to specific carbons, but are de-localized due to the resonance caused by the circular structure of the molecule. The unique nature of benzene’s double bonding makes benzene act somewhat like a saturated hydrocarbon. It is slow to react or is un-reactive, in contradiction to what might otherwise be normal expectations.
Carboxylic Acid
A carboxylic acid is an organic compound that contains a carboxyl group (C(O)OH). The general formula of a carboxylic acid is R-C(O)OH with R referring to the rest of the (possibly quite large) molecule. Carboxylic acids occur widely, and include the amino acids and acetic acid (active ingredient in vinegar).
Salts and esters of carboxylic acids are called carboxylates. When a carboxyl group is deprotonated, its conjugate base forms a carboxylate anion. Carboxylate ions are resonance stabilized and this increased stability makes carboxylic acids more acidic than alcohols. Carboxylic acids can be seen as reduced or alkylated forms of the Lewis acid carbon dioxide; under some circumstances they can be decarboxylated to yield carbon dioxide.
Ester
Esters are usually derived from an inorganic acid or organic acid in which at least one -OH (hydroxyl) group is replaced by an -O-alkyl (alkoxy) group. Commonly esters are derived from carboxylic acids and alcohol. Esters comprise most naturally occurring fats and oils, which are fatty acidesters of glycerol. Esters with low molecular weight are commonly used as fragrances and found in essential oils and pheromones. Phosphoesters form the backbone of DNA molecules. Nitrate esters, such as nitroglycerin, are known for their explosive properties, while polyesters are important plastics, with monomers linked by ester moieties.
Ether
Ethers are a class of organic compounds that contain an ether group — an oxygen atom connected to two alkyl or aryl groups — of general formula R–O–R’. A typical example is the solvent and anesthetic diethyl ether, commonly referred to simply as “ether” (CH3-CH2-O-CH2-CH3). Ethers are common in organic chemistry and pervasive in biochemistry, as they are common linkages in carbohydrates and lignin.
Ketone
A ketone (or alkanone) is an organic compoundwith the structure RC(=O)R’, where R and R’ can be a variety of carbon-containing substituents. Ketones and Aldehydes are simple compounds that contain a carbonyl group (a carbon-oxygen double bond). They are considered “simple” because they don’t have reactive groups like -OH or -Cl attached directly to the carbon atom in the carbonyl group, as in carboxylic acids containing -COOH. Examples include many sugars (ketoses) and the industrial solvent acetone.
Phenol
Phenol, also known as carbolic acid, is an aromatic organic compound with the molecular formula C6H5OH. It is a white crystalline solid that is volatile. The molecule consists of a phenyl group (-C6H5) bonded to a hydroxyl group (-OH). It is mildly acidic, but requires careful handling due to its propensity to cause chemical burns.
Although similar to alcohols, phenols have unique distinguishing properties. Unlike in alcohols where the hydroxyl group is bound to a saturated carbon atom,in phenols the hydroxyl group is attached to an unsaturated aromatic (alternating double and single bond) hydrocarbon ring such as benzene. Consequently, phenols have greater acidity than alcohols due to stabilization of the conjugate base through resonance in the aromatic ring.
Phenyl Group
In organic chemistry, the phenyl group or phenyl ring is a cyclicgroup of atoms with the formula C6H5. Phenyl groups are closely related to benzene. Phenyl groups have six carbon atoms bonded together in a hexagonal planar ring, five of which are bonded to individual hydrogen atoms, with the remaining carbon bonded to a substituent. Although often depicted with alternating double and single bonds, phenyl groups are chemically aromatic and show nearly equal bond lengths between carbon atoms in the ring.
Propyl Group
Propyl is a linear three-carbon alkyl substituent with chemical formula -C3H7. It is the substituent form obtained by removing one hydrogen atom attached to the terminal carbon of propane. A propyl substituent is often represented in organic chemistry with the symbol Pr (not to be confused with the element praseodymium).
Linear propyl is sometimes termed normal and written with a prefix n- (i.e., n-propyl). However, n-is redundant because the absence of any prefix implies an unbranched propyl.
isopropyl (fully systematic name 1-methylethyl)
An isomeric form of propyl named 1-methylethyl or isopropyl obtained by removing a hydrogen ion (proton) attached to the middle carbon of propane.
Butyl Group
butyl is a four-carbon alkyl radical or substituent group with general chemical formula -C4H9, derived from either of the two isomers of butane.
The isomer n-butane can connect either at one of the two terminal carbon atoms or at one of the two internal carbon atoms, giving rise to two “-butyl” groups:
Normal butyl or n-Butyl: CH3–CH2–CH2–CH2– (fully systematic name: butyl)
Secondary butyl or sec-Butyl: CH3–CH2–CH(CH3)– (fully systematic name: 1-methylpropyl)
sec-Butyl (fully systematic name 1-methylpropyl)
butyl is a four-carbon alkyl radical or substituent group with general chemical formula -C4H9, derived from either of the two isomers of butane.
The isomer n-butane can connect either at one of the two terminal carbon atoms or at one of the two internal carbon atoms, giving rise to two “-butyl” groups:
Normal butyl or n-Butyl: CH3–CH2–CH2–CH2– (fully systematic name: butyl)
Secondary butyl or sec-Butyl: CH3–CH2–CH(CH3)– (fully systematic name: 1-methylpropyl)
isobutyl (systemic name 2-methylpropyl)
Butyl is a four-carbon alkyl radical or substituent group with general chemical formula -C4H9, derived from either of the two isomers of butane.
The branched isomer of butane, isobutane, can connect either at one of the three terminal carbons or at the central carbon, giving rise to another two groups:
Isobutyl: (CH3)2CH–CH2– (fully systematic name: 2-methylpropyl)
Tertiary butyl, tert-Butyl or t-butyl: (CH3)3C– (fully systematic name: 1,1-dimethylethyl)
tert-Butyl (fully systemic name 1,1-dimethylethyl)
Butyl is a four-carbon alkyl radical or substituent group with general chemical formula -C4H9, derived from either of the two isomers of butane.
The branched isomer of butane, isobutane, can connect either at one of the three terminal carbons or at the central carbon, giving rise to another two groups:
Isobutyl: (CH3)2CH–CH2– (fully systematic name: 2-methylpropyl)
Tertiary butyl, tert-Butyl or t-butyl: (CH3)3C– (fully systematic name: 1,1-dimethylethyl)
Propyl Group
Propyl is a linear three-carbon alkyl substituent with chemical formula -C3H7. It is the substituent form obtained by removing one hydrogen atom attached to the terminal carbon of propane. A propyl substituent is often represented in organic chemistry with the symbol Pr (not to be confused with the element praseodymium).
Linear propyl is sometimes termed normal and written with a prefix n- (i.e., n-propyl). However, n-is redundant because the absence of any prefix implies an unbranched propyl.
isopropyl (fully systematic name 1-methylethyl)
An isomeric form of propyl named 1-methylethyl or isopropyl obtained by removing a hydrogen ion (proton) attached to the middle carbon of propane.
Butyl Group
butyl is a four-carbon alkyl radical or substituent group with general chemical formula -C4H9, derived from either of the two isomers of butane.
The isomer n-butane can connect either at one of the two terminal carbon atoms or at one of the two internal carbon atoms, giving rise to two “-butyl” groups:
Normal butyl or n-Butyl: CH3–CH2–CH2–CH2– (fully systematic name: butyl)
Secondary butyl or sec-Butyl: CH3–CH2–CH(CH3)– (fully systematic name: 1-methylpropyl)
sec-Butyl (fully systematic name 1-methylpropyl)
butyl is a four-carbon alkyl radical or substituent group with general chemical formula -C4H9, derived from either of the two isomers of butane.
The isomer n-butane can connect either at one of the two terminal carbon atoms or at one of the two internal carbon atoms, giving rise to two “-butyl” groups:
Normal butyl or n-Butyl: CH3–CH2–CH2–CH2– (fully systematic name: butyl)
Secondary butyl or sec-Butyl: CH3–CH2–CH(CH3)– (fully systematic name: 1-methylpropyl)
isobutyl (systemic name 2-methylpropyl)
Butyl is a four-carbon alkyl radical or substituent group with general chemical formula -C4H9, derived from either of the two isomers of butane.
The branched isomer of butane, isobutane, can connect either at one of the three terminal carbons or at the central carbon, giving rise to another two groups:
Isobutyl: (CH3)2CH–CH2– (fully systematic name: 2-methylpropyl)
Tertiary butyl, tert-Butyl or t-butyl: (CH3)3C– (fully systematic name: 1,1-dimethylethyl)
tert-Butyl (fully systemic name 1,1-dimethylethyl)
Butyl is a four-carbon alkyl radical or substituent group with general chemical formula -C4H9, derived from either of the two isomers of butane.
The branched isomer of butane, isobutane, can connect either at one of the three terminal carbons or at the central carbon, giving rise to another two groups:
Isobutyl: (CH3)2CH–CH2– (fully systematic name: 2-methylpropyl)
Tertiary butyl, tert-Butyl or t-butyl: (CH3)3C– (fully systematic name: 1,1-dimethylethyl)
1°, 2°, 3°, 4° carbon
Primary carbons, are carbons attached to one other carbon. (Hydrogens – although usually 3 in number in this case – are ignored in this terminology).
Secondary carbons are attached to two other carbons.
Tertiary carbons are attached to three other carbons.
Quaternary carbons are attached to four other carbons.
1°, 2°, 3° carbocation
A primary carbocation is attached to one other carbon, a secondary to two, and a tertiary to three. You can’t have a quaternary carbocation without violating the octet rule (you’d need an extra empty p orbital for that, bringing the total to 5).
1°, 2°, 3° alcohol
Alcohols also follow the primary/secondary/tertiary nomenclature. The rule for alcohols is that they are named according to the number of carbons attached to the carbon bearing the hydroxyl group: in other words, whether the hydroxyl bound to a primary, secondary, or tertiary carbon. You can’t have a quaternary alcohol – again, that would involve breaking the octet rule.
1°, 2°, 3°, 4° amine
Amines are named according to the number of carbons attached to nitrogen. Primary, secondary, and tertiary amines are nitrogens bound to one, two and three carbons, respectively. Since the nitrogen has a lone pair, it is still possible to form another bond to carbon. These are called quaternary amines, although they bear a positive charge on nitrogen and are not at all basic. They are often referred to as quaternary ammonium salts. You’ll see the -ium ending quite a bit – it designates a positively charged species.
1°, 2°, 3° amide
A primary amide is bound to one carbon – the carbonyl carbon. Successive substitutions of hydrogen for carbon turn the amide into secondary and tertiary amides. [You might ask - can you have quaternary amides? Well, yes. Except nobody calls them that - they’re quite unstable, and go by another name.]
Amide
An amide, also known as an acid amide, is a compound with the functional group RnE(O)xNR’2 (R and R’ refer to H or organic groups). Most common are “organic amides” (n = 1, E = C, x = 1), but many other important types of amides are known including phosphor amides (n = 2, E = P, x = 1 and many related formulas) and sulfonamides (E = S, x= 2).[1] The term amide refers both to classes of compounds and to the functional group (RnE(O)xNR’2) within those compounds.
