Carboxilic acids, amides and esters

1. CARBOXILIC ACIDS

2. •Carboxylic acids are compounds which contain a
carboxy group -COOH group.
•General formula R-COOH or
•The rule is that functions assume their distinct
identity when separated by –CH2– groups.
•Thus, the carbonyl, C=O, and hydroxy, OH, of a
carboxylic acid, RCOOH, are part of a single
function and are NOT "alcohol-plus-ketone":

3. Nomenclature of Carboxylic Acids
•As with aldehydes, the carboxyl group must be
located at the end of a carbon chain.
• In the IUPAC system of nomenclature the
carboxyl carbon is designated #1, and other
substituents are located and named accordingly.
•The characteristic IUPAC suffix for a carboxyl
group is "oic acid", and care must be taken not
to confuse this systematic nomenclature with the
similar common system.

4. Examples

7. Name the following
A) B)
C) D)

8. Draw the following and give the IUPAC name
•Formic acid
•Malonic Acid
•Acetic acid
•Propionic acid

9. AMIDES

10. •Amides are amine derivatives of carboxylic
acids.derived from carboxylic acids.
•A carboxylic acid contains the -COOH group,
and in an amide the -OH part of that group is
replaced by an -NH
2
group.
•Amides contain the -CONH
2
group.
•General Formula R-CONH
2
or

11. Nomelnclature
HCONH
2
methanamide
CH
3
CONH
2
ethanamide
CH
3
CH
2
CONH
2
propanamide
Notice that in each case, the name is derived
from the acid by replacing the "oic acid" ending
by "amide".

12. Nomenclature
•If the chain was branched, the carbon in the
-CONH
2
group counts as the number 1 carbon
atom. For example:

14. ESTERS

15. •The simple esters tend to have pleasant odors.
•The characteristic flavors and fragrances of
flowers and fruits are due to compounds with
the ester functional group.
•General Formula R-COO-R’ or R-CO-OR’
or

17. Nomenclature
•Esters are produced when carboxylic acids
(COOH) are heated with alcohols (OH) in the
presence of an acid catalyst.
•An ester name has two parts - the part that
comes from the acid ending ““ateate” ” and the part
that shows the alkyl group coming fro the
allcohol ending “ylyl”

18. Nomenclature
•Notice that the ester is named the opposite way
around from the way the formula is written.
•The "ethanoate" bit comes from ethanoic acid.
The "ethyl" bit comes from the ethyl group on
the end.

19. Examples

20. Name

21. Draw

22. Answers

23. Making esters
The chemistry of the reaction
•Esters are produced when carboxylic acids
(COOH) are heated with alcohols (OH) in the
presence of an acid catalyst. The catalyst is
usually concentrated sulphuric acid.
•The equation for the reaction between an acid
RCOOH and an alcohol R'OH (where R and R'
can be the same or different) is:

24. •So, for example, if you were making ethyl ethanoate
from ethanoic acid and ethanol, the equation would
be:

25. Doing the reactions (Laboratory)
On a test tube scale
•Carboxylic acids and alcohols are often warmed
together in the presence of a few drops of
concentrated sulphuric acid in order to observe
the smell of the esters formed.