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Understanding Alcohols: Properties & Reactions

Alcohols are formed when hydrogen atoms in alkanes are replaced by hydroxyl (-OH) groups. The presence of the -OH group allows alcohols to hydrogen bond, giving them higher melting and boiling points than alkanes. Lower molecular weight alcohols are soluble in water due to hydrogen bonding from their -OH groups. Alcohols can undergo oxidation to form aldehydes, ketones, or carboxylic acids depending on whether the alcohol is primary, secondary, or tertiary. They can also form esters through esterification reactions with acids. Certain alcohols will produce a yellow iodoform precipitate in iodoform tests, indicating their structure.

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8 views4 pages

Understanding Alcohols: Properties & Reactions

Alcohols are formed when hydrogen atoms in alkanes are replaced by hydroxyl (-OH) groups. The presence of the -OH group allows alcohols to hydrogen bond, giving them higher melting and boiling points than alkanes. Lower molecular weight alcohols are soluble in water due to hydrogen bonding from their -OH groups. Alcohols can undergo oxidation to form aldehydes, ketones, or carboxylic acids depending on whether the alcohol is primary, secondary, or tertiary. They can also form esters through esterification reactions with acids. Certain alcohols will produce a yellow iodoform precipitate in iodoform tests, indicating their structure.

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chenjude
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Alcohols

Alcohols formed when a hydrogen in an alkane has been replaced by OH, hydroxyl group.
General formula CnH2n+1OH.

Physical Properties
The presence of the OH group means molecules can hydrogen bond to each other, therefore the
intermolecular forces are stronger than in alkanes and as a result the mpt and bpt are higher than in the
corresponding alkanes.
The solubility in water of alcohols is due to the presence of the OH group, lower members of the groups
are soluble however as the molecules get larger, solubility decreases.
Alcohols can be classified based on the position of the OH group in the molecule.

Reactions of alcohols
1. Oxidation

Primary alcohols

Secondary alcohol ketones

Tertiary alcohols resists oxidation

aldehydes

carboxylic acids

KMnO4/H+ or K2Cr2O7/H+ can be used to oxidise primary and secondary alcohols. They are reducing
agents and therefore give the expected colour changes with these oxidizing agents. There is no colour
change with tertiary alcohols.

Aldehyde

Carboxylic acid

XS alcohol

XS oxidizing agent

Distill off aldehyde as it forms

Reflux to keep aldehyde in mixture

2. Esterification
Alcohol + acid ester + water

Write an equation for the formation of a) ethyl butanoate.

b) propyl methanoate

3. Iodoform Reaction
Used to identify alcohols with a particular structure.

When alcohols with this structure are heated with I 2 in NaOH, yellow crystals of iodoform are formed.
This test can therefore be used to distinguish between alcohols with this structure and those without.

Circle the following alcohols which will give a positive iodoform test?

4. Reactions with metals


Alcohols and reactive metals form alkoxide salts and hydrogen. Draw the structural formula below the
name of the compound.

2CH3CH2OH + 2Na 2CH3CH2O-Na+ + H2


Ethanol

sodium ethoxide

2CH3CH2CH2OH + Ca (CH3CH2CH2O)2Ca2+ + H2
Propan-1-ol

calcium propoxide

Complete the equation for the reaction of phenylmethanol with barium.

5. Reaction with Concentrated H2SO4


This results in dehydration reactions either within the molecule (alkene formation) or between molecules
(ether formation), water is a second product in both reactions.

Write a balanced equation for the following reaction.

6. Reaction with halogenating agents


-SOCl2

sulphur dichloride oxide

-PCl5

phosphorous pentachloride

These convert the alcohol to a chloroalkane. The reaction with PCl 5 is violent with copious fumes of
HCl(g) evolved. SOCl2 also produces white fumes of HCl(g) and also SO 2. These reactions can be used to
show an OH group is present in an unknown (once other groups like -COOH which give the same
observation have been eliminated as possibilities).
Watch PCl5 react with an alcohol and an acid [Link]

See some of the above reactions in this animation [Link]

[Link] November 22nd, 2014

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