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01/10/07 Carboxylic Acids and their Derivatives Carboxylic acids ..oic acid Esters ....yl ...

oate

Acid Chlorides (Acyl Chlorides) ....oyl Chloride

O C OH
Carboxylic Acids Chemical Properties of Carboxylic Acids They Behave as Acids Acid Proton (H+) Donor a) Acid + Base Salt + water

O C O

O C Cl

Ethanoic acid + NaOH Sodium Ethanoate + Water CH3CH2OH + NaOH CH3COONa+ + H2O Definaition of a Salt When a Metal Ion/Ammonium Ion replaces the acidic proton in an acid E.g.1. Benzoic acid + KOH Potassium Benzoate + Water

O C O H
C6H5COOH E.g.2. +

K+OH

O C O K
C6H5COOK+
+

H2O

Ethanoic acid + Calcium Hydroxide Calcium Ethanoate + H2O

2CH3COOH + Ca(OH)2

O H3C C O 2 Ca
2+

+ 2H2O

1 b) Acid + Carbonate Salt + CO2 + H2O NOTE: CAN be used as a test for Carboxylic acids as 2CH3COOH + Na2CO3 2CH3COONa+ + CO2(g) + H2O bubbles given off. -Alcohols wont react Written Bywith Faz014@hotmail.com carbonate

c) Acid + Reactive metal Salt + H2(g) CH3COOH + Na CH3COONa+ + H2(g) Ethanol + Na Sodium ethoxide + H2(g) CH3CH2OH + Na CH3CH2ONa + H2 d) Alcohols + Carboxylic Acids Ester + H2O

NOTE: CANNOT be used as a test for Carboxylic acids as bubbles given off. -Alcohols react with reactive metal to produce H2

C OH

O H O C C

O C O C C

H2O

Take out H2O Acid Cat: H2SO4

H3C C OH H2

O H O C H

O H3C C O C H H2
Functional group

H2O

2Ethanol + Benzene-1,4-dioic Acid

Diethyl Benzene-1,4-dioate

C H3C CH2OH
HO
O C

C
OH HOH2C CH3
O C

H3C C O H2

O C CH3 H2

2H2O

e) Carboxylic Aid + Chlorinating Agent Acyl(Acid)chlorides i. Ethanoic Acid + PCl5 Ethanoyl + HCl + POCl3 Chloride NOTE: CAN be used as a test for Carboxylic acids as white fumes given off.

O H3C C OH

PCl5

H3C C Cl

H Cl

Reacts very violently and spits

Misty white fumes

POCl3
2

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ii. Ethanoic Acid + SOCL2

Ethanoyl + HCl + SO 2 Chloride

O H3C C OH

SOCl2

H3C C Cl

H Cl

SO2

Very reactive and used to make other chemicals o good synthetic chemical o Lachromatory Makes you cry f) Carboxylic Acids can be reduced Carboxylic Acid Aldehyde Alcohols Carboxylic Acids are difficult to reduce o need a powerful reducing agent, LiAlH4 (non aq) Will reduce anything even water CH3COOH + [4] CH3CH2OH + H2O

O H3C C

+ [4] H3C
OH

CH2OH

H2O

Esters Hydrolysis of an Ester Ester + H2O Alcohol + Carboxylic Acid

Catalyst: Acid or Base a) Acid catalysed hydrolysis of an ester Propyl ethanoate + H2O Propene + Ethanoic Acid Catalyst: H + H2O
+ (aq)

O C CH3 HO

O CH3CH2CH2 O C CH3

CH3CH2CH2OH
3

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b) Base catalysed hydrolysis of an ester Propyl ethanoate + H2O Propene + Ethanoic Acid + + H2O

O C CH3 HO

O CH3CH2CH2

O C CH3

CH3CH2CH2OH

The carboxylic acid will react with the base to form a salt once the hydrolysis reaction is done Acid + Base + Alcohol Salt + Alcohol

O H3C C O Na
+

Also known as Soap AcylChlorides (Acid Chlorides) Chemical properties of AcylChlorides

All reactions are very violent and spit HCl is given off and as observation seen as Misty white Fumes AcylChlorides react with anything that has a H in its functional group

1. Making a Carboxylic Acid Ethanoyl Chloride + Water HCl + Ethanol

O H3C C Cl
2. Making an Acid Amide Benzoyl Chloride + Ammonia Benzoic Acid Amide + HCl + H2O

HCl

+ H3C

C OH

O C Cl
+ NH3

O C NH2
4 + HCl

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3. Making an Ester Methyl Propanoyl Chloride + TriChloroPhenol TriChlorophenyl MethylPropanoate

Cl

CH3 H3C C C H

+
Cl

HO Cl

Cl

CH3 O Cl H3C C C O H Cl
+

Cl
HCl

This is 100% conversion, there is no equilibrium state 4. Manking a Peptide Ethanoyl Chloride + Ethylamine EthylEthanamide

O H3C C Cl
+

H H

H N C CH3 H

O H H3C C N C2H5

HCl

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