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Notes On Alcohols, Haloalkanes and Analysis

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21 views2 pages

Notes On Alcohols, Haloalkanes and Analysis

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fletcherberryheath2006
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Notes on Alcohols, Haloalkanes and Analysis

4.2.1 Alcohols

Alcohols contain an -OH group and follow the general formula CnH2n+2O. They can be produced via
two main methods of fermentation and hydration. Alcohols are named according to IUPAC rules
and have the suffix -ol. Alcohols can be primary (1°), secondary (2°) or tertiary (3°), depending on
the position of the hydroxyl group.

Primary alcohols have the hydroxyl group connected to a carbon atom which is connected to two
hydrogen atoms and one other carbon atom. Secondary alcohols have the hydroxyl group connected
to a carbon atom which is connected to one hydrogen atom and two other carbon atoms. Tertiary
alcohols have the hydroxyl group connected to a carbon atom which is connected to no hydrogen
atoms and three other carbon atoms.

Alcohols are polar molecules since there is a large difference in electronegativity between carbon
and oxygen. The oxygen is very electronegative, so can hydrogen bond to water molecules. This
ability means that alcohols are water soluble.

Hydrogen bonds are a much stronger intermolecular force than London forces so more energy is
required to overcome them. Alcohols have both types of intermolecular force present between
molecules, so are much less volatile than alkanes which only have London forces present.

Reactions of Alcohols:
Combustion: When burned in air, alcohols react with oxygen to produce carbon dioxide and water.
Alcohols make good fuels by reacting in this way as lots of energy is also released.

2CH4O + 3O2 = 2CO2 + 4H2O

Reactions with Halogenating Agents:


Alcohols can react with halogenating agents via nucleophillic substitution. The -OH group is
replaced by a halogen, forming a haloalkane.

Pcl5 is used to produce chloroalkanes. This can be used as a test for alcohols because their reaction
with Pcl5 produces white steamy fumes which tern damp blue litmus paper red.

A reaction mixture of concentrated sulfuric acid and potassium bromide can be used to produce
bromoalkanes. The potassium bromide reacts with the sulfuric acid to form Hbr. This then reacts
with the alcohol to produce the bromoalkane.

C2H6O + HBr = C2H5Br + H2O

A reaction mixture of red phosphorus with iodine can be used to produce iodoalkanes. First, the
phosphorus reacts with the iodine to produce phosphorus(III) iodide. This then reacts with the
alcohol to form the iodoalkane.

2P + 3I2 = 2PI3

3C2H6O + PI3 = 3C2H5 + H3PO3

Elimination Reactions:
Alkenes can be formed from the dehydration of alcohols, where a molecule of water is removed
from the molecule. In order to do this, the alcohol is heated with concentrated phosphoric acid.

Oxidation of Alcohols:
Primary and secondary alcohols can be oxidised to produce various products byut tertiary alcohols
are not easily oxidised.

When primary alcohols are heated in the prescenec of acidified potassium dichromate(VI), they are
oxidised to aldehydes. Distillation is required to separate the aldehyde product.

When an aldehyde is heated further with acidified potassium dichromate (VI) under reflux
conditions, the alehyde is oxidised to produce carboxylic acids. This shows primary alcohols are
oxidised to aldehydes and then to carboxylic acids.

Secondary alcohols can be oxidised to ketones when heatted in the prescence of acidified potassium
dichromate(VI).

Potassium Dichromate(VI) (K2Cr2O7):


Potassium Dichromate(VI) is used in the oxidation of alcohols as the oxidising agent. It is reduced
as the alcohol is oxidised. A colour change from orange to green is observed when the alcohol is
oxidised with potassium dichromate(VI). This colour change occurs due to a change in thee
oxidation state of the chromium ion.

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