Exp 9 Alcohols and Phenols

Organic chemistry lab

Experiment (8)
Alcohols and Phenols
(chemical Test )

Fayda Salameh
Objective

1. To observe the solubility of alcohols relative to their chemical structure.

2. chemical tests will be performed to distinguish primary, secondary and
tertiary alcohols and a color test to performed phenol.
Alcohol
 The general formula of an alcohol is ROH in which the R is an aliphatic
hydrocarbon group.
 Like water, alcohols show hydrogen bonding. As the chain of the R

group increases the hydrocarbon character of the compound
overshadows the polar character of the OH group.
 Consequently, the solubility and boiling point of an alcohol are affected

by the length of the carbon chain and the shape of the molecule.
How shape affected solubility and boiling point of an alcohol?
 The short chain alcohols are soluble in water, whereas the longer chain
alcohols are insoluble in water (more than 4 carbon for each OH the
compound become non soluble).
 molecule which is more compact (i.e., more branched) will be more

soluble in water and will have a lower boiling point than the straight
chain isomer.
Alcohols classification
 Alcohols are classified as primary, secondary and tertiary according to
the number of alkyl groups directly attached to the carbinol carbon
Reactions of alcohols involve the breaking of either of two bonds: the

O-H bond as in reactions with bases and esterification reactions, or
the C-OH bond leading to dehydration and substitution reactions.
Phenol
Aromatic alcohols, in which R is an aromatic ring.
Not: alkyl alcohols have an -OH group, they do not ionize in water, whereas
phenols ionize like acids (donating a proton to water).
Phenol
 The most common reactions of phenols involve breaking the O-H bond
and the usual electrophilic aromatic substitution at the aromatic ring.
 Protonation of the hydroxyl group and loss of a water molecule as in

alcohols would give a phenyl cation which is very unstable and difficult to
form.
 phenols do not undergo substitution of the hydroxyl group either by the
SN1 or SN2 mechanisms.
 But Since the aromatic nucleus is electron rich, direct attack by
nucleophiles as in SN1or SN2 reactions is not possible.
Phenols from Alcohols
The characteristic property that differentiates phenols from alcohols is

acidity. Phenols are stronger acids than alcohols and react with sodium
hydroxide, whereas alcohols do not. The reason for this difference is that the
phenoxide ion is resonance-stabilized whereas the alkoxide ion is not.

1. Solubility in Water
 Alcohols of low molecular weight

are water soluble due to their ability
to form hydrogen bonds with water.
Solubility in water decreases with
increasing molar mass but increases
with branching and with the number
of hydroxyl (OH) groups.
2. Acid Properties of Alcohols
 Alcohols react with metallic sodium with the evolution of hydrogen. The
relative acidities of alcohols and consequently their relative rates of
reaction with sodium are in the order:
primary > secondary > tertiary.

3. Chromic Acid Oxidation of Alcohols
 Primary and secondary alcohols are oxidized by chromic acid to the
corresponding carboxylic acids and ketones respectively.
 Tertiary alcohols are generally unreactive under similar conditions
When alcohols are oxidized they reduce chromium (VI) to Cr (III) changing
the color of the solution from orange to green.
3. Chromic Acid Oxidation of Alcohols
4. The Lucas Test
 The Lucas reagent is a solution of zinc chloride in concentrated HCl. The
test depends on a difference in the rate of reaction of these alcohols. used to
distinguish between primary, secondary and tertiary alcohols.
 With this reagent the order of reactivity is typical of compounds reacting by
the SN1 mechanism. The zinc chloride (a Lewis acid) assists in breaking the
C-OH bond.
4. The Lucas Test
Tertiary alcohols react immediately. The test tube will get hot, and because
the chloride is insoluble two layers may be apparent.
5. The Iodoform Test
 The iodoform test is used to identify secondary alcohols that have a
methyl group on the alcohol carbon. This type of alcohol will react
with I2 in NaOH to give a yellow precipitate of iodoform, CHI 3.
6. Acidity of Phenols
 Phenols are weak acids – in water, they ionize slightly to form

phenoxide ion and hydronium ion, which makes the solution acidic.
 Because phenols are weak acids, they will react with bases. If phenol is
reacted with NaOH (a strong base), it is completely converted to the
phenoxide ion, which is soluble in water because it is charged.
6. Acidity of Phenols
7. Iron Chloride Test
 The presence of a phenolic (or enolic group) in a compound is indicated
by the formation of a violet (or red) iron complex when treated with a
ferric chloride solution.
Component of this experiment
Good Luke

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Organic chemistry lab

1. To observe the solubility of alcohols relative to their chemical structure.

 Like water, alcohols show hydrogen bonding. As the chain of the R

 Consequently, the solubility and boiling point of an alcohol are affected

 molecule which is more compact (i.e., more branched) will be more

Reactions of alcohols involve the breaking of either of two bonds: the

 Protonation of the hydroxyl group and loss of a water molecule as in

The characteristic property that differentiates phenols from alcohols is

phenoxide ion is resonance-stabilized whereas the alkoxide ion is not.

 Alcohols of low molecular weight

primary > secondary > tertiary.

 Phenols are weak acids – in water, they ionize slightly to form

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