Chemsitry 4.5 - Carboxylic Acids and Their Derivatives
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- Created by: Tashaleese_99
- Created on: 20-05-17 10:15
C. acids act as...
WEAK ACIDS. They partially dissociate in water and transfer a hydrogen from the -COOH.
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Formula of the hydroxide ion?
H3O+
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Which two compounds can be oxidised to form a carboxylic acid?
Primary alcohols or aldehydes.
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How can you form an aromatic carboxylic acid?
1. Oxidise an aromatic primary alcohol. 2. Oxidise the methyl side chain of an aromatic compound.
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Conditions for the oxidation of aromatic primary alcohols?
Acidified potassium dichormate or potassium manganate, reflux.
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Conditions for the oxidation of an aromatic compound with a methyl side chain?
Alkaline potassium manganate and heat (followed by acidification to convert the potassium salt initially produced into the acid).
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Conditions for the decarboxylation of c.acids?
Soda lime, heat.
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What happens in decarboxylation?
The -COOH group or -COONa group is replaced by a hydrogen atom.
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Name the three compounds that can be used to represent soda lime in an equation.
Calcium hydroxide, calcium oxide and sodium hydroxide.
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Common side products of a reaction involving calcium hydroxide?
Calcium carbonate (and water if the hydrogens are not balanced).
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Common side products of a reaction involving calcium oxide?
Calcium carbonate (and water if the hydrogens are not balanced).
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Common side products of a reaction involving sodium hydroxide?
Sodium carbonate (and water if the hydrogens are not balanced).
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Conditions for esterification?
Concentrated sulfuric acid and reflux.
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The esters produced during esterification can be hydrolysed back into carboxylic acids. State the basic and acidic conditions for this reaction.
BASIC CONDITIONS - aqueous NaOH and reflux. ACIDIC CONDITIONS - dilute hydrochloric or sulfuric acid and reflux.
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Conditions for the formation of acid chlorides from carboxylic acids?
Either phosphorus trichloride, phosphorus pentanchloride or sulfer dichloride oxide is used. Conditions must also be anhydrous.
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What side products are produced when phosphorus pentachloride is used?
HCl gas and POCl3.
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What side products are produced when phosphorus trichloride is used?
Phosphoric acid (H3PO3).
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What side products are produced when sulfer dichloride oxide is used?
Sulfer dioxide and HCl gas.
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Which of the three reagents is preferred?
Sulfer dichloride oxide - only gaseous co-products are formed.
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The acid chlorides produced in these reactions can be hydrolysed, reforming the initial carboxylic acid. Name the mechanism by which this occurs.
Nucleophilic addition elimination.
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What is a zwitterion?
A molecule that possesses an atom/group with a positive charge and an atom/group with a negative charge.
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What is an oxoanion?
An anion formed from the loss of hydrogen atoms from oxygen atoms.
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Carboxylic acids can be converted into ammonium salts, followed by amides. Conditions?
Ammonia or ammonium carbonate is required to produce the ammonium salt. The compound is then heated to form an amide.
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Amide functional group?
Common functional group is an oxygen bonded to NH2. However, it can also be simply an oxygen bonded to a N which has two R groups attached.
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Amides can be converted into nitriles by...
Dehydration.
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Conditions for the dehydration of amides?
Heat and phosphorus (V) oxide, P4O10.
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Conditions for the formation of hydroxynitriles and nitriles from halogenoalkanes?
Sodium or potassium cyanide in ethanol, reflux.
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Mechanism by which this reaction occurs?
Nucleophilic substitution.
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Why should water not be present in this reaction?
Could substitute the -OH group rather than the -CN group.
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Why can this reaction not occur using chlorobenzene?
The ring carbon atoms are not susceptible to attack by a nucleophile due to their increased electron density.
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Why is this method useful?
It increases the length of the carbon chain.
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Acidic conditions for the hydrolysis of nitriles?
Dilute acid, reflux (WATER IS INCLUDED IN THE EQUATION).
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Basic conditions for the hydrolysis of nitriles?
Aqueous NaOH, reflux (WATER IS INCLUDED IN THE EQUATION).
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The hydrolysis of nitriles will form...
Firstly, an amide. This is then hydrolysed to produce a c.acid or its sodium salt.
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When could a sodium salt be produced?
When using NaOH.
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Acidic conditions for the hydrolysis of amides?
Dilute acid, heat (WATER IS INCLUDED IN THE EQUATION).
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Basic conditions for the hydrolysis of amides?
NaOH, heat (NOTE: CONDITIONS AREN'T AQUEOUS SO WATER IS NOT INCLUDED IN THE EQUATION).
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Conditions for the reduction of nitriles?
Lithium aluminium hydride, ether.
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When nitriles are reduced they produce...
A PRIMARY AMINE.
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Other cards in this set
Card 2
Front
Formula of the hydroxide ion?
Back
H3O+
Card 3
Front
Which two compounds can be oxidised to form a carboxylic acid?
Back
Card 4
Front
How can you form an aromatic carboxylic acid?
Back
Card 5
Front
Conditions for the oxidation of aromatic primary alcohols?
Back
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