Alcohol, Phenols, Ethers Flashcards
CHEM: Alcohol, Phenols, Ethers
Oxygen is a Group VIA Element – has 6 valance electrons
- Two lone pairs
- Two bonding pairs, i.e., it can form two covalent bond
Bonding in organic compounds:
Carbon forms four bonds
– Hydrogen forms one bond
– Oxygen forms two bonds
An organic compound in which an —OH group is
bonded to a saturated carbon atom.
Alcohol
A carbon atom that is bonded to four
other atoms
Saturated carbon atom
COMMON NAMES FOR ALCOHOLS
Name all of the carbon atoms of the molecule as a single
alkyl group.
rule 1
COMMON NAMES FOR ALCOHOLS
Add the word alcohol, separating the worlds with a
space.
rule 2
IUPAC RULES FOR NAMING ALCOHOLS
Name the longest carbon chain to which the hydroxyl
group is attached.
rule 1
IUPAC RULES FOR NAMING ALCOHOLS
Number the chain starting at the end nearest the
hydroxyl group, and use the appropriate number to indicate the
position of the — OH group.
rule 2
IUPAC RULES FOR NAMING ALCOHOLS
Name and locate any other substituents present
rule 3
IUPAC RULES FOR NAMING ALCOHOLS
In alcohols where the—OH group is attached to a carbon
atom in a ring, the hydroxyl group is assumed to be on carbon 1.
rule 4
__________ is possible for alcohols containing
three or more carbon atoms.
Constitutional isomerism
Two types of isomers
– Skeletal isomers
– Positional isomers
Good fuel and used as a solvent in paints
METHYL ALCOHOL (METHANOL)
Also called grain alcohol as obtained by fermentation of grains
like corn, rice and barley.
ETHYL ALCOHOL (ETHANOL)
is a three-carbon monohydroxy alcohol
Isopropyl alcohol
_______ is a triol with three -OH groups attached on three
adjacent carbon atoms
Glycerol
have both polar and nonpolar character
Alcohol molecules
the ______ group is nonpolar part of the molecule
The alkyl (R)
The ________ group is polar part of the molecule
hydroxyl
have higher boiling points than alkanes of
similar molecular mass.
Alcohols
Prepared by hydration of alkenes
PREPARATION OF ALCOHOLS
-Like other hydrocarbons alcohols are also flammable.
- The _______ products are carbon dioxide and water.
COMBUSTION
Also known as an elimination reaction
INTRAMOLECULAR ALCOHOL DEHYDRATION
The major product formed in an intramolecular alcohol
dehydration reaction is the alkene that has the greatest number
of alkyl groups attached to the carbon atoms of the double bond
ZAITISEV’S RULE
In this reaction, two molecules of alcohol combine to form an
ether (Condensation reaction)
INTERMOLECULAR ALCOHOL DEHYDRATION
Addition of oxygen or removal of hydrogen
OXIDATION
In this reaction a halogen atom is substituted for the hydroxyl
group producing an alkyl halide.
HALOGENATION
It is possible to synthesize polymeric alcohols with structures
similar to those of substituted polyethylene
POLYMERIC ALCOHOLS
An organic compound in which an —OH group is
attached to a carbon atom that is part of an aromatic carbon ring
system
Phenol
An aromatic carbon ring system from which one
hydrogen atom has been removed.
Aryl group
Low-melting solids or oily liquids at room temperature.
Phenols
Unlike alcohols, phenols are weak acids in solution.
ACIDITY OF PHENOLS
Oxygen bonded to two carbon atoms (functional group)
Ethers
IUPAC NOMENCLATURE
Select the longest carbon chain and use its name as the
base name.
rule 1
IUPAC NOMENCLATURE
Change the “-yl” ending of the other hydrocarbon group
to “-oxy” to obtain the alkoxy group name − Examples: methyl
becomes methoxy, ethyl becomes ethoxy, etc.
rule 2
IUPAC NOMENCLATURE
Place the alkoxy name, with a locator number, in front of
the base chain name.
rule 3
Ethers and alcohols with the same number of carbon atoms
and the same degree of saturation have the same molecular
formula
FUNCTIONAL GROUP ISOMERISM
The boiling points of ethers are similar to those of alkanes of
comparable molecular mass and are much lower than those
of alcohols of comparable molecular mass
PHYSICAL PROPERTIES
Ethers are Flammable, e.g., Diethyl ether has boiling point
of 35C and therefore a flash-fire hazard.
CHEMICAL PROPERTIES
Contain the ether functional groups as part of
a ring system (heterocyclic organic compounds).
CYCLIC ETHERS
are named in the same way as alcohols in the IUPAC
system, except that the “–ol” becomes ______
“-thiol.”
Have strong, disagreeable odor
PROPERTIES OF THIOLS
An organic compound in which a sulfur
atom is bonded to two carbon atoms by single bonds.
Thioethers (or sulfides)
are more reactive than their alcohol and ether
counterparts
Thiols
_________ is a gas at room temperature and ethyl methyl
sulfide is a liquid.
Dimethyl sulfide
