Oxygen is group 6A
Needs to form two bonds
to get an octet.
Structural characteristics of alcohols
• Alcohols have the general formula:
R-OH
where “R” involves a saturated C-atom (bound to
hydrogens and/or other carbons).
• For example:
Structural characteristics of alcohols
• Condensed structural formulas or line-angle structures are
commonly used for depicting alcohols
IUPAC name
1-Propanol
1-Butanol
2-Propanol
2-Methyl-1-propanol
(Isobutanol)
Nomenclature for alcohols
Common names for alcohols
2-Methyl-2-butanol 2-Methylcyclopentanol
Alcohols with more than one OH group
• Polyhydroxyl alcohols possess more than one
OH group.
• Alcohols which possess two OH groups are
called “diols” and those with three OH groups
are called “triols”
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Preparation of alcohols
• Alcohols can be prepared by hydration of alkenes :
H2SO4
H2
Chemical reactions of alcohols
• Combustion – makes CO2 and H2O
• Dehydration (loss of water – intramolecular) – make an alkene
• Dehydration (loss of water – intermolecular) – makes an ether
• Oxidation – makes a carboxylic acid
• Halogenation – makes a halogenated alkane
Chemical reactions of alcohols
Combustion reactions
2 9 O2 6CO2 8H2O
Chemical reactions of alcohols
Elimination reactions
H2SO4
H-OH
180oC
H2SO4
H-OH
180oC
Chemical reactions of alcohols
Elimination reactions
A-B
1-butene
2-butene
Use Zaitsev’s Rule to predict which alkene will be produced in the greater amount
Chemical reactions of alcohols
Elimination reactions
H2SO4
+ H2O
180oC
2-butene
major product
Chemical reactions of alcohols
Elimination reactions
Hydration
H2O
Dehydration
Chemical reactions of alcohols
Condensation reactions
H2SO4
H2O
140oC
H2O
Dimethyl ether
oxidation oxidation
reduction reduction
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Oxidation of Alcohols
25
Chemical reactions of alcohols
Oxidation reactions
• Primary and secondary alcohols can be oxidized by mild oxidizing agents to
produce compounds with C-O double bonds (aldehydes, ketones,
carboxylic acids).
[O] [O]
a primary alcohol
[O]
mild oxidizing
agent = [O]
a ketone
a secondary alcohol
No H on OH-bearing
carbon to remove here.
[O]
no reaction
a tertiary alcohol
Structural characteristics of phenols
• Phenols are aromatic compounds that bear a OH group.
3-Bromophenol
4-Ethyl-3-iodophenol
Structural characteristics of phenols
ortho-Cresol meta-Cresol
para-Cresol
Catechol Resorcinol
Hydroquinone
H2O H3O+
Occurrence and uses of phenols
BHT
BHAs (butylated hydroxyanilines) (butylated hydroxytoluene)
antioxidants
Nomenclature for ethers
• Ethers are organic compounds in which two saturated carbon
atoms are bound through a single oxygen atom.
• Examples:
common names
Nomenclature for ethers
• The IUPAC system for naming ethers:
1. Longest continuous carbon chain is used as parent name (might
have substituents)
2. Other chain is named as an alkoxy-substituent: change the “yl” part
of the other alkyl chain to “oxy” (e.g. methyl to methoxy)
3. Name as alkoxy name then the parent chain. Number the alkoxy
substituent to indicate where it attaches to the parent alkane.
4-Methoxy-2-butanol
Physical and chemical properties of ethers
a hydroperoxide a peroxide