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Carboxylic Acids

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0% found this document useful (0 votes)
13 views29 pages

Carboxylic Acids

Uploaded by

Mariana Rocha
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Let’s Recall

Homologous Functional General Formula


Formula Suffix Example
Series Group (m≥0, n≥1)

Alkane Alkyl RH CnH2n+2 -ane Ethane

Alkene Alkenyl R2C=CR2 CnH2n -ene Ethene

Alcohol Hydroxyl ROH CnH2n+1OH -ol Methanol


 Belongto a homologous series of organic
compounds similar to alkanes, alkenes and
alcohols

 Thehydrocarbon chains contain the


functional group -COOH (carbonyl group)

Structural Formula Chemical Formula

CH3COOH

= or
CH3CO2H
 Methanoic acid  Ethanoic acid  Propanoic acid
 Total of one  Total of two  Total of three
carbon atom carbons atoms carbon atoms
(meth-) (eth-) (propan-)
 C0H1COOH C1H3COOH  C2H5COOH

*Take note of the functional group’s location, highlighted by the


dotted box
 Replace the ‘e’ with ‘oic acid’ at the end of
the name of the hydrocarbon

Example:

H H H O
H C C H H C C O H
H H H
ethane ethanoic acid
 Similar to its alcohol:
 Colourless liquid at room temperature & relatively
low boiling point of 118oC
 Completely miscible (able to dissolve) in water
 Has a characteristic ‘sour-ish’ smell
 Is a weak acid of pH 3
Are carboxylic acids the same as the acids we
have learnt about in the chapter on acids and
bases?
Watch and observe!!
 Ascarboxylic acid is weak, its reactions
produce the same outcomes as those learnt
from the chapter of Acids, Bases and Salts

 But, the reactions are less vigorous


Weak acids (pH ≈ 3).
Most of the acid molecules are unionised in water.

For example: 1.0 mol/dm3 solution of ethanoic acid

CH3COOH(aq) CH3COO (aq) + H+(aq)

Pure acid 1000 0 0


Acid in water 996 4 4
Reaction with bases
to form a salt and water

For example:

CH3COOH + NaOH CH3COONa + H2O


Reaction with reactive metals
to form a salt and hydrogen

For example:

2CH3COOH + Mg (CH3COO)2Mg + H2
Reaction with carbonates
to form a salt, carbon dioxide and water

For example:

2CH3COOH + Na2CO3 2CH3COONa + CO2 + H2O


Ethanoic acid is the most important organic
acid
It is used in vinegar as preservative and
flavourings.
Organic acid Where it is found
Lactic acid Sour milk
Oxalic acid Rhubarb plant
Citric acid Limes, lemons
Formic acid Insect bites
Tartaric acid Grape juice
Acetic acid Vinegar
Malic acid Apples and pears
Making of drugs, dyes, paints, insecticides,
plastics.

Making of esters.
 Carboxylic acids reacts with alcohols
to form esters
in the presence of a few drops of concentrated
sulphuric acid as catalyst

General equation:

acid + alcohol ester + water


 Have the general formula RCOOR’

R C O R'

Functional group of
ester
Alcohol + Carboxylic acid  Ester + Water

Alkanol + Alkanoic acid  Alkyl alkanoate + Water

R’OH + RCOOH  RCOOR’ + H2O


H H O H

H C C O H + H O C C H

H H H

+ O
H H
H O H H O H

H C O C C H O
H C OH + H O C C H
+ H H
H H H H

methanol + ethanoic acid methyl ethanoate + water

CH3OH + CH3COOH CH3COOCH3 + H 2O


Chemical Molecular Structural Alcohol Organic
name formula formula used acid used

methyl ethanoic
HCOOH H3C C methanol
ethanoate O CH3 acid

ethyl H2 ethanoic
CH3COOH C C ethanol
ethanoate H3C O CH3 acid
Are esters
acidic, neutral
or basic?
 Esters are neutral compounds with a sweet smell

 Colourless and insoluble in water


 Fruity flavours for perfumes, sweets, drinks and
cakes

◦ Artificial pineapple flavour is an ester made from


ethanol and butanoic acid, called ethyl butanoate.

 Solvents for organic compounds, such as glues,


varnishes and paints.
Summary
Homologous Functional General Formula
Formula Suffix Example
Series Group (m≥0, n≥1)

Alkane Alkyl RH CnH2n+2 -ane Ethane

Alkene Alkenyl R2C=CR2 CnH2n -ene Ethene

Alcohol Hydroxyl ROH CnH2n+1OH -ol Methanol

Carboxylic acid Carboxyl RCOOH CmH2m+1COOH -oic acid Ethanoic acid

Alkyl Ethyl
Ester Ester RCOOR’ CmH2m+1COOCnH2n+1
alkanoate butanoate
How it all ties up

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