Chapter 14: Some compounds with oxygen, sulfur or a halogen
Alcohol is a compound that has an ¬OH group bonded to a saturated, carbon atom, R¬OH.
Phenol is a compound that has an ¬OH group bonded directly to an aromatic, benzene-like ring, Ar¬OH.
Ether is a compound that has an oxygen atom bonded to two organic groups, R¬O¬R.
Steps to name an alcohol:
STEP 1: Name the parent compound.
Find the longest chain that has the hydroxyl substituent attached, and name the chain by replacing the -e ending of the corresponding alkane with -ol.
STEP 2: Number the carbon atoms in the main chain.
The carbon bearing the ¬OH must be assigned the lowest index number possible when numbering the chain.
Begin at the end nearer the hydroxyl group, ignoring the location of other substituents for now.
In a cyclic alcohol, begin with the carbon that bears the ¬OH group and proceed in a direction that gives the other substituents the lowest possible numbers.
STEP 3: Write the name, placing the number that locates the hydroxyl group immediately before the “ol” ending of the alcohol name.
Number all other substituents according to their positions, and list them alphabetically.
Note that in a cyclic alcohol, it is not necessary to use the number 1 to specify the location of the ¬OH group.
When the two ¬OH groups are on adjacent carbons (commonly called vicinal diols), diols are often referred to by the common name glycols.
Strictly speaking, any diol having the ¬OH groups on adjacent carbons can be called a glycol, but the term “glycol” is preferably reserved for two compounds, ethylene glycol and propylene glycol. Ethylene glycol is the simplest glycol.
Alcohols with one substituent are said to be primary (1°), those with two substituents are secondary (2°), and those with three substituents are tertiary (3°).
Alcohols undergo loss of water (dehydration) upon treatment with a strong acid catalyst; the reaction is typically driven to completion by heating. The ¬OH group is lost from one carbon and an ¬H is lost from an adjacent carbon to yield an alkene product and water.
An organic oxidation is one that increases the number of C¬O bonds and or decreases the number of C¬H bonds.
An organic reduction is one that decreases the number of C¬O bonds and or increases the number of C¬H bonds.
Alkoxide ion is the anion resulting from the removal of the H from an alcohol, RO-.
Thiols (R¬SH), also called thioalcohols or mercaptans, are sulfur analogs of alcohols (an analog is a molecule that has a structure very similar to that of another one in all but one or two key aspects).
Thiols react with mild oxidizing agents, such as Br2 in water or even O2, to yield disulfides, RS¬SR. Two thiols join together in this reaction, the hydrogen from each is lost, and a bond forms between the two sulfurs.
Alkyl halide is a compound that has an alkyl group bonded to a halogen atom, R¬X.
Aryl halide A compound that has an aromatic group bonded to a halogen atom, Ar¬X.
Stereochemistry is the study of molecules that have the same overall connectivity of atoms but differ in how those atoms are arranged in three-dimensional space.
Isomers that have the same formula and whose atoms have the same connections but different spatial arrangements are known as stereoisomers.
Configurations :Stereoisomers that cannot be converted into one another by rotation around a single bond.
Chirality is having right- or left handedness with two different mirror image forms.
Achiral is the opposite of chiral, having superimposable mirror images and thus no right- or left-handedness.
A carbon atom that is BOTH tetrahedral AND has four different groups attached is referred to as a chiral carbon atom, or a chiral center (or stereocenter).
Enantiomers (optical isomers) is the two mirror-image forms of a chiral molecule.
Alcohol is a compound that has an ¬OH group bonded to a saturated, carbon atom, R¬OH.
Phenol is a compound that has an ¬OH group bonded directly to an aromatic, benzene-like ring, Ar¬OH.
Ether is a compound that has an oxygen atom bonded to two organic groups, R¬O¬R.
Steps to name an alcohol:
STEP 1: Name the parent compound.
Find the longest chain that has the hydroxyl substituent attached, and name the chain by replacing the -e ending of the corresponding alkane with -ol.
STEP 2: Number the carbon atoms in the main chain.
The carbon bearing the ¬OH must be assigned the lowest index number possible when numbering the chain.
Begin at the end nearer the hydroxyl group, ignoring the location of other substituents for now.
In a cyclic alcohol, begin with the carbon that bears the ¬OH group and proceed in a direction that gives the other substituents the lowest possible numbers.
STEP 3: Write the name, placing the number that locates the hydroxyl group immediately before the “ol” ending of the alcohol name.
Number all other substituents according to their positions, and list them alphabetically.
Note that in a cyclic alcohol, it is not necessary to use the number 1 to specify the location of the ¬OH group.
When the two ¬OH groups are on adjacent carbons (commonly called vicinal diols), diols are often referred to by the common name glycols.
Strictly speaking, any diol having the ¬OH groups on adjacent carbons can be called a glycol, but the term “glycol” is preferably reserved for two compounds, ethylene glycol and propylene glycol. Ethylene glycol is the simplest glycol.
Alcohols with one substituent are said to be primary (1°), those with two substituents are secondary (2°), and those with three substituents are tertiary (3°).
Alcohols undergo loss of water (dehydration) upon treatment with a strong acid catalyst; the reaction is typically driven to completion by heating. The ¬OH group is lost from one carbon and an ¬H is lost from an adjacent carbon to yield an alkene product and water.
An organic oxidation is one that increases the number of C¬O bonds and or decreases the number of C¬H bonds.
An organic reduction is one that decreases the number of C¬O bonds and or increases the number of C¬H bonds.
Alkoxide ion is the anion resulting from the removal of the H from an alcohol, RO-.
Thiols (R¬SH), also called thioalcohols or mercaptans, are sulfur analogs of alcohols (an analog is a molecule that has a structure very similar to that of another one in all but one or two key aspects).
Thiols react with mild oxidizing agents, such as Br2 in water or even O2, to yield disulfides, RS¬SR. Two thiols join together in this reaction, the hydrogen from each is lost, and a bond forms between the two sulfurs.
Alkyl halide is a compound that has an alkyl group bonded to a halogen atom, R¬X.
Aryl halide A compound that has an aromatic group bonded to a halogen atom, Ar¬X.
Stereochemistry is the study of molecules that have the same overall connectivity of atoms but differ in how those atoms are arranged in three-dimensional space.
Isomers that have the same formula and whose atoms have the same connections but different spatial arrangements are known as stereoisomers.
Configurations :Stereoisomers that cannot be converted into one another by rotation around a single bond.
Chirality is having right- or left handedness with two different mirror image forms.
Achiral is the opposite of chiral, having superimposable mirror images and thus no right- or left-handedness.
A carbon atom that is BOTH tetrahedral AND has four different groups attached is referred to as a chiral carbon atom, or a chiral center (or stereocenter).
Enantiomers (optical isomers) is the two mirror-image forms of a chiral molecule.