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Org. Chem. (Chapter 8)
Org. Chem. (Chapter 8)
OH OH OH
C C
CH3 HO H
3-Phenyl-2-butanol
2-Methyl-2-pentanol Cis-1,4-Cyclohexanediol
Common Names that are accepted by IUPAC
CH2OH CH3
H2C CHCH2OH H3C C OH
Allyl alcohol
Benzyl alcohol (2-Propen-1-ol) CH3
(Phenylmethanol)
Tert-Butyl alcohol
(2-Methyl-2-propanol)
Naming Phenols
Note that -phenol is used as the parent name rather than –benzene.
OH
O2N 2,4-Dinitrophenol
NO2
Properties of Alcohols & Phenols: Hydrogen Bonding
Like water, they form hydrogen bonds in the liquid state.
Acidity & Basicity
[ or ArOH + HX
+ -
ArOH2 X ]
- Both are weakly acidic.
- They dissociate in dilute aqueous solution by donating a
proton to water, generating H3O+ & an alkoxide ion, RO− or
phenoxide ion, ArO− .
Alcohols react with: alkali metals; strong bases like sodium
hydride (NaH), sodium amide (NaNH2) & Grignard Reagents
(RMgX) to form alkoxides.
- +
CH3OH + NaH CH3O Na + H2
Methanol Sodium methoxide
- +
CH3CH2OH + NaNH 2 CH3CH2O Na + NH2
Ethanol Sodium ethoxide
-+
OH + CH3MgBr O MgBr + CH4
cyclohexanol Bromomagnesiumcyclohexoxide
Phenols are more acidic than alcohols because the phenoxide ion
formed, is resonance-stabilized.
The resonance-stabilized phenoxide ion is more stable
than the alkoxide ion.
Preparation of Alcohols
+ HOMgBr
Formaldehyde
O O
C C
R H R
R
An aldehyde
A ketone
Naming Aldehydes
O
O
CH3CH2CCH2CH2CH3
1 2 3 4 5 6 CH3CH CHCH2CCH3
6 5 4 3 2 1
3-Hexanone 4-Hexen-2-one
O O
CH3CH2CCH2CCH3
6 5 4 3 2 1
2,4-Hexanedione
A few ketones are allowed by IUPAC to retain their common names:
Exercises:
1)
2) Draw Structures corresponding to the following names:
(a) 3-Methylbutanal
(b) 4-Chloro-2-pentanone
(c) Phenylacetaldehyde
(d) 2-(1-Chloroethyl)-5-methylheptanal