Study Set Content:
- Introduction of a protecting group to block interfering function
- Execution of the desired reaction
- Removal of the protecting group
Protection of Alcohols
Phenols are synthesized using
isopropylbenzene
isopropylbenzene commonly called
cumene
- Process yields two valuable chemicals at the same time
- Process yields two valuable chemicals at the same time
Reactions of Phenols
- Electrophilic aromatic substitution reactions
Makes phenols substrates for:
- Electrophilic halogenation
- Nitration
- Sulfonation
- Friedel-Crafts reactions
Oxidation of a phenol yields a
2,5-cyclohexadiene-1,4-dione, or quinone
is used in more complex cases
Fremy's salt [(KSO3)2NO
Quinones can be easily reduced to hydroquinones by reagents such as
NaBH4 and SnCl2
Alcohols have a strong C-O stretching absorption near
- 1050 cm-1
Characteristic O–H stretching absorption occurs at
- 3300 to 3600 cm-1
Pharmaceutical Uses
alcohol
mportant solvents and synthesis intermediates
Ethanol, CH2CH2OH, called ethyl alcohol, is a
solvent, fuel, and beverage
are used in alcoholic beverages
alcohols
- are mainly used in pharmaceutical products where they are used as antiseptic substances.
phenols
- Alcohols are among the most versatile of all organic compounds, occur widely in nature, and are important industrially
- Alcohols are among the most versatile of all organic compounds, occur widely in nature, and are important industrially
- are protected because Grignard reagents can't be prepared from alkyl halides that contain reactive functional groups in the same molecule
Functional groups
- are aromatic counterparts of alcohols but are more acidic
Phenols
Phenols can be oxidized to
quinones
quinones can be reduced back to
hydroquinones
