CARBOXYLATE ACID AND

ESTHER
Dwi Antika Br Nasution (4193111047)
Dinda Erliananda (4193111011)
Elfina Siahaan (4191111046)
Nurul Afifah Syahputri (4193111014)
 CARBOXYLATE ACID

Carboxylic acids are part of hydrocarbon

Carboxylic acid structure
compounds, because carboxylic acids are also
composed of carbon and hydrogen. Carboxylic acids
are also called alkanoic acids which are a group of
aliphatic organic acids that have a carboxyl
functional group. Carboxylic acid is a derivative of
alkanes in which an H atom from alkanes is
replaced by a -COOH group.

The other ways can be show :

R-COOH, R-CO2H
 Common names:
HCO2H formic acid
NAME’S OF CH3CO2H acetic acid
CH3CH2CO2H propionic acid
CARBOXYLATE CH3CH2CH2CO2H butyric acid
ACID CH3CH2CH2CH2CO2H valeric acid
CH3(CH2)4CO2H caproic acid
CH3(CH2)6CO2H caprylic acid
 FR
Common Names
• Many aliphatic acids have historical names.
• Positions of substituents on the chain are labeled with Greek letters.

Br CH3
Cl O
CH3CH2CH2CHCOOH CH3CHCH2COOH
CH3CH2CHC OH
 bromovaleric acid  -methylbutyric acid -chlorobutyric acid
isovaleric acid 4
IUPAC NAMES OF CARBOXYLIC ACIDS FR
• Do you know any names?
• They are named by taking the name of the alkane with the same
number of C atoms and replacing the -ane with an – oic acid
• The carbon of the carboxyl group is #1
Carboxylic acids
• H-COOH methanoic acid

• CH3 -COOH ethanoic acid

• CH3-CH2-COOH propanoic acid

EXAMPLE OF IUPAC NAME

O O CH3 CH3 O

H C OH H3C C OH H3C C C C OH
H H
methanoic acid ethanoic acid
2,3-dimethylbutanoic acid
 Carboxylic acids syntheses: FR
1. oxidation of primary alcohols
RCH2OH + K2Cr2O7  RCOOH
2. oxidation of alkil arenes
ArR + KMnO4  ArCOOH
3. carbonation of Grignard reagents
RMgX + CO2  RCO2MgX + H+  RCOOH
4. hydrolysis of nitriles
RCN + H2O, H+  RCOOH
Add a footer 7
 FR

carboxylic acids are more soluble in water than are alcohols, ethers, aldehydes, and ketones of comparable
molecular weight
 FR
Chemical reactions
1. React with bases or alkalis to form salts

R COOH + NaOH R COO- Na+ + H2O

2. React with PCl5 or SOCl2 at room temperature to form acid chlorides

R COOH + PCl5 R COCl + POCl3 + HCl

R COOH + SOCl2 R COCl + SO2 + HCl

3. React with alcohols in the presence of concentrated H2SO4 to form esters. FR
R COOH + R' OH R COOR' + H2O

4. Reduction – React with LiAlH4 to form primary alcohols

LiAlH4 RCH2OH + H2O
R COOH + 4 [H]
5. React with electropositive metals to form salts and H2 gas.
O

R COOH + K R C O- K+ + 1/2 H2

6. Ammonium salts of carboxylic acids undergo dehydration to form amides.

O O

R C O- NH4+ R C NH2 + H2O

amides
 What are Esther?
How are Esther made?
 Formed when an alcohol reacts with a carboxylic acid.
 Very slow reaction, unless! an acid catalyst used (usually
sulphuric acid)
 A condensation reaction
 The condensation reaction between the hydroxyl group and
the carboxylic acid known as esterification.
 Reverse reaction = ester hydrolysis
 Names of esters
Naming end in –oate.
Named after alcohol & carboxylic acid from which
they are derived.
O let’s name
C CH3 some esters!

CH3 CH2 O
ethyl ethanoate
this part comes from the this part from the acid
alcohol & is named after it and is named after it
 Structural formulae
Although the previous structural formula are the clearest way of
showing esters, they can draw out in a shortened form.
In this version
ethyl Ethanoate the acid part has
Or… O been written first
Either… O
CH3 CH2 O C CH3 CH3 C O CH2 CH3

 Identify the group attached to the C=O – this is from

the acid
 The group attached to the –O- is from the alcohol.
 Wait! What’s that smell?
ester fragrance
ethyl methanoate raspberries
3-methylbutyl ethanoate pears
ethyl 2-methylbutanoate apples
phenylmethyl ethanoate jasmine

• Esters have strong, sweet smells.

• Their bouquet is often floral or fruity.
• This means they are used in food flavourings & perfumes.
• Also, very good at dissolving organic compounds so often used
as solvents.
 Esters from phenols
• -OH group in phenol less reactive to
esterification, requires a more
vigourous reagent.
• Use of ethanoic acid in esterification is OH
also known as ethanoylation.
• Ethanoic anhydride is a more
vigourous ethanoylating agent
 Esters from phenols
• Ethanoic anhydride used as it is reactive but not too
dangerous.
• Ethanoyl chloride is much more reactive, but, also toxic
and hazardous to use.
• Ethanoic anhydride & ethanoyl chloride are described as
acylating agents
using an acylating agent is the only way to esterify a phenol
alcohols can be esterified using acylating agents or by reacting with a
carboxylic acid.
 Ester hydrolysis
 Breakdown of an ester by water.
 Process sped up by catalysis
 Can use an acid to catalyse (H2SO4)
 Alkali catalysts (e.g. sodium hydroxide) can also be used
but instead of producing carboxylic acid a carboxylate
salt is formed.
 Alkaline hydrolysis goes to completion & hence is usually
preferred.
 R O H O

⇋
C R’
+ O
C R’ R O
+
H O This is why it is a condensation reaction
H2O
because water is produced!

Definition of a condensation reaction = two

molecules reacting to form a larger molecule with
the elimination of a small molecule such as water
 O
CH ethyl methanoate
CH3 CH2 O
O
C CH2 CH3 methyl propanoate
CH3 O
O
CH methyl methanoate
CH3 O
FORWARD REACTION = condensation reaction,
the esterification of an alcohol using
acid catalyst under reflux.
R O H O

⇌
C R’
+ O
C R’ R O
+
H O
H2O
REVERSE REACTION = ester hydrolysis, same
catalyst works for both forward & reverse
reactions.
 ethyl ethanoate ethanol
O CH3 CH2 OH
C CH3
CH3 CH2 O
+
+
OH- → O
-O
C CH3

not a reaction that exists ethanoate ion

in equilibrium (unlike
using acid catalyst)
 Critical Book report
Published: 2016
Title: Introduction to
Organic Chemistry

City: United States of

Author: William H. Brown
America
and Thomas Poon

Publisher: Wiley Binder

Version Edition: Sixth Edition

First Book ( mainly book)

22
 Summary of first book

In this book is explain about :

▸ The definition of carboxylate
Carboxylic acid is carboxyl groups, which have formula R- C𝑂2 H or 𝐶𝑛 𝐻2𝑛+1 C𝑂2 H,
with the functional group of –COOH

▸ The name’s IUPAC and Trivial of carboxylate

In IUPAC Nomenclatur is same with alkane but dropping the final ‐ e from the
name of the parent alkane and adding the suffix ‐ oic , followed by the word acid.
We number the chain beginning with the carbon of the carboxyl group. Because
the carboxyl carbon is understood to be carbon 1, there is no need to give it a
number. In the Trivial / common have the specially rules with the greek letters
23
PHYSICAL PROPERTIES OF CARBOXICATE ACID
Carboxylic acids have significantly higher boiling points than other types of organic
compounds of comparable molecular weight, such as alcohols, aldehydes, and ketones

THE DEFINITION OF ESTHER

Ester is a combination of the name of the hydrocarbon radical of the alcohol plus
the name of the parent acid with its ending changed –ate.
ReAction of esther
Hydrolysis reaction: Hydrolysis of esters in aqueous acid is also an equilibrium reaction
and proceeds by the same mechanism as esterification, except in reverse. Reaction with
Ammonia: The reaction product between an ester and ammonia is an amide and an
alcohol. Transesterification: If an ester is reacted with an alcohol, a new ester and a new
alcohol will be obtained. Reaction with Grignard reagents: Reaction of an ester with a
Grignard reagent involves the formation of two successive tetrahedral carbonyl addition
compounds. Esters Reduction: An ester is reduced by lithium aluminum hydride to two
alcohols. 24
 ADVANTAGES AND DEFICIENCY OF BOOKS
ADVANTAGES OF FIRST BOOK
• The material in the book is presented in full
and detail. The material is explain clearly
about the definition of carboxylate acid and
ester nomenclatur with IUPAC Or Trivial of
Carboxylate acid is explain in this book with
a table, and physical properties of
carboxylate acid, fisher eterification and eter
reaction , are too explain in this book and
they are not explain in book 2 and book 3
• There is an explanation of each sub material
• There is a clear picture
• The material systematically arranged
• This book is very suitable as learning source
25
DEFICIENCY OF FIRST BOOK
• The material in this book is difficult to
understand because this book explain
with deeper so for beginer it so difficult
to understand of this book
• In this book is not give many example
of carboxylate acid and ester
• There is not carboxylate reaction. In
this book only explain about the ester
reaction
 Published: May 2006 Title: Fundamentals of
Chemistry

City: United States Author: David Goldberg

Publisher: McGraw-Hill
Edition: fifth edition
Science/Engineering/Math

Second Book

26
 Summary of second book

• Definition of carboxylate acid

In this book, carboxylate acid said with organic acid An organic acid has the
functional group :

• As a rule, organic acids are weak; the hydrogen atom ionizes to a slight extent in
water.
• The name of an ester is a combination of the name of the hydrocarbon radical of
the alcohol plus the name of the parent acid with its ending changed –ate. The
ester of ethyl alcohol plus acetic acid is thus ethyl acetate. Many simple ester have
pleasant odors. Ethyl acetate is used to provide an odor to artificial fruits, as a
solvent for lacquers and varnishes, in the manufacture of photographic films, and
for many esters occur naturally; their sweet odors are responsible for the
fragrances of flowers and fruits.
27
 Advantages and disadvantages
ADVANTAGES OF SECOND BOOK
• This book use a language that is easy to
understand
• This book is simple because just tell us
about the basic so is suitable for a
beginner. In the second book just only
tell about general formula of
carboxylate acid and nomenclatur
IUPAC of carboxylate acid
• This book has many exercise so we can
practice our abilities
• This book has summery at the end of
the chapter so we can easily review the
theory
DEFICIENCY OF SECOND BOOK
• This book just tell us the basic so is not suitable for
the person that want to learn deeper and in the
second book there isn’t the definition of carboxylate
acid and ester if it compare with first book, the first
book more detail explain about the definition of
carboxylate acid and ester
• This book didn’t tell us about how to named the
esters reaction in detailed explanation (about
IUPAC and Trivial name) then in this second book
only give example of reaction of acetic acid if
comparison with book 1 it more give an example of
reaction Ester ,
• This book didn’t tell us about structural formula of
esters in detailed explanation
28
 Summary of third book

Carboxylic Acids
The general formula for Table 5.6. Naming Carxylic Acids
carboxilyc acids is R-CO2H or
CnH2n+1CO2H, with the functional group Names of some carboxylic acids
of –COOH, or : Formula Name

HCO2H or HCOOH Methanoic acid

CH3COOH Ethanoic acid

CH3CH2COOH Propanoic acid

The firstmolecule of methanoic acid is CH3CH2CH2COOH Butanoic acid

HCO2H which has a value of n equals to
CH3CH2CH2CH2COOH Pentanoic acid
zero.

29
 ADVANTAGES AND DISADVANTAGES
ADVANTAGES OF THIRD BOOK
The language used in this
book is quite easy to understand
because the language is brushy,
dense, and clearly and not
convoluted.
DEFICIENCY OF THIRD BOOK
• In this book, if we want to understand organic
chemistry especially carboxylic acids and
ester cannot be used because this book only
contains carboxylic acids, even though ester is
a derivative of carboxylic acid and is not
explained in this book.
• In the carboxylic acid material contained in
this book, the material does not cover all
material, only explains what carboxylic acid
is, its formula and functional groups, as well
as the naming where only a few naming
examples
30
Conclusion and Recommendation

31
 Conclusion and Recommendation

Conclusion
▸ Carboxylic acid is carboxyl groups, which have formula R-CO2H or
CnH2nO2, with the functional group of –COOH
▸ Ester is a combination of the name of the hydrocarbon radical of the
alcohol plus the name of the parent acid with its ending changed –
ate.
▸ Esters have hydrolysis reaction, reaction with ammonia,
transesterification, reaction with grignard reagents, esters
reduction.

32
 Conclusion and Recommendation

Recommendation
We recommend book I for those who want to learn about
carboxylate acid and ester with deep, because book I is expalain about
carboxylate acid and ester so detail. Even this book is written in english,
but the words are easy to read . So you can practice your english too. But
for beginner you can use of book II because that book is simple because
just tell us about the basic so is suitable for a beginner and that book has
many exercise so we can practice our abilities and has too summery at
the end of the chapter so we can easily review the theory

33
Group 3 Thank You.
RESIGN