Flashcards - Topic 33 Carboxylic Acids and Derivatives - CAIE Chemistry A-Level

CAIE Chemistry A-level
Topic 33 - Carboxylic Acids and

Derivatives
(A level only)
Flashcards
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How do carboxylic acids react to form
acyl chlorides?
How do carboxylic acids react to form acyl
chlorides?
Carboxylic acids react with sulfur dichloride
oxide to form an acyl chloride, sulfur dioxide
and hydrogen chloride.
CH3COOH + SOCl2 → CH3COCl + SO2 + HCl
What is the chemical equation for the
reaction between ethanoic acid and
sulfur dichloride oxide?
What is the chemical equation for the reaction
between ethanoic acid and sulfur dichloride oxide?
CH3COOH + SOCl2 → CH3COCl + SO2 + HCl
How is methanoic acid further oxidised?
How is methanoic acid further oxidised?
Although methanoic acid is a carboxylic acid, it also has an

aldehyde functional group. This means the aldehyde group
can be oxidised further by using Tollens’ reagent or
Fehling’s solution.
Methanoic acid is oxidised to carbon dioxide and water.
oxidation of methanoic acid?
What is the chemical equation for the oxidation of
methanoic acid?
HCOOH + [O] → CO2 + H2O
How is ethanedioic acid oxidised further?
How is ethanedioic acid oxidised further?
Ethanedioic acid is oxidised to carbon

dioxide and water using warm acidified
potassium manganate(VII) solution.
oxidation of ethanedioic acid?
What is the chemical equation for the oxidation of
ethanedioic acid?
(COOH)2 + [O] → 2CO2 + H2O
State the relative acidities of carboxylic
acids, alcohols and phenols
State the relative acidities of carboxylic acids,
alcohols and phenols
Carboxylic acids → Phenol → Alcohols

→ Decreasing acidity →
Explain the relative acidities of carboxylic
acids, alcohols and phenols
Explain the relative acidities of carboxylic acids, alcohols
and phenols
● Carboxylic acids are the most acidic as the carboxylate ion has a delocalised pi system
that develops over the -COO- group. This distributes the negative charge, making the
carboxylate ion more stable.
● Phenols are more acidic than alcohols because the the phenoxide ion is relatively
stable. The lone pair on the oxygen is delocalised into the pi system so the negative
charge is dispersed. This makes phenol more likely to donate a hydrogen ion compared
with alcohols.
● Alcohols are the least acidic because of the positive inductive effect. In the alkoxide ion,
the alkyl groups “push” electrons away from themselves, increasing the electron density
of the oxygen, making it more likely to bond to a hydrogen ion and reform an alcohol.
What determines the acidity of chlorine
substituted ethanoic acids?
What determines the acidity of chlorine substituted
ethanoic acids?
You can strengthen an acid by pulling charge away from the
-COO- end. This can be done by adding a chlorine atom to the
chain. Chlorine is very electronegative and so will have a
tendency to attract electrons towards itself.
Therefore, the more chlorines bonded, the stronger the acid.
How do acyl chlorides react with water?
How do acyl chlorides react with water?
Hydrolysis reaction:
The acyl chloride reacts with water to form a
carboxylic acid and hydrochloric acid.
hydrolysis of ethanoyl chloride?
What is the chemical equation for the hydrolysis of
ethanoyl chloride?
CH3COCl + H2O → CH3COOH + HCl
How do acyl chlorides react with
alcohols?
How do acyl chlorides react with alcohols?
Acyl chlorides react with alcohols to form

an ester and hydrochloric acid:
CH3COCl + CH3OH → CH3COOCH3 + HCl
How do acyl chlorides react with phenol?
How do acyl chlorides react with phenol?
An acyl chloride reacts with phenol to form

an aromatic ester and hydrochloric acid.
CH3COCl + C6H5OH → CH3COOC6H5 + HCl
How do acyl chlorides react with
ammonia?
How do acyl chlorides react with ammonia?
Acyl chlorides react with ammonia to form

a primary amide and hydrochloric acid:
CH3COCl + NH3 → CH3CONH2 + HCl
How do acyl chlorides react with a
primary amine?
How do acyl chlorides react with a primary amine?
Acyl chlorides react with a primary amine to

form a secondary amide and hydrochloric acid:
CH3COCl + CH3NH2 → CH3CONHCH3 + HCl
Compare the relative ease of hydrolysis
of acyl chlorides, alkyl chlorides and aryl
chlorides
Compare the relative ease of hydrolysis of acyl
chlorides, alkyl chlorides and aryl chlorides
● Acyl chlorides react vigorously with cold water to

produce a carboxylic acid and hydrogen chloride gas.
E.g. CH3COCl + H2O → CH3COOH + HCl
● Alkyl chlorides have almost no reaction with water.
● Aryl chlorides have no reaction with water.
How do esters undergo acid hydrolysis?
How do esters undergo acid hydrolysis?
Heat the ester under reflux with dilute aqueous acid.

The ester will be hydrolysed into a carboxylic acid
and alcohol.
The reaction is slow and reversible.
CH3COOCH3 + H2O ⇌ CH3COOH + CH3OH
How do esters undergo base hydrolysis?
How do esters undergo base hydrolysis?
Heat the ester under reflux with a dilute alkali. The

ester will be hydrolysed into the salt of the
carboxylic acid, and the alcohol. The reaction is
one-way and faster than acid hydrolysis.
CH3COOCH3 + NaOH → CH3COO-Na+ + CH3OH

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CAIE Chemistry A-level

Topic 33 - Carboxylic Acids and

CH3COOH + SOCl2 → CH3COCl + SO2 + HCl

Although methanoic acid is a carboxylic acid, it also has an

HCOOH + [O] → CO2 + H2O

Ethanedioic acid is oxidised to carbon

(COOH)2 + [O] → 2CO2 + H2O

Carboxylic acids → Phenol → Alcohols

Therefore, the more chlorines bonded, the stronger the acid.

CH3COCl + H2O → CH3COOH + HCl

Acyl chlorides react with alcohols to form

An acyl chloride reacts with phenol to form

Acyl chlorides react with ammonia to form

Acyl chlorides react with a primary amine to

● Acyl chlorides react vigorously with cold water to

Heat the ester under reflux with dilute aqueous acid.

Heat the ester under reflux with a dilute alkali. The

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