organic reactions

1. ORGANIC REACTIONS

2. 5 Types of Reactions
1. Condensation Reactions
2. Addition Reactions
3. Substitution Reactions
4. Elimination Reactions
5. Oxidation Reactions
ORGANIC REACTIONS

3. CONDENSATION REACTIONS
(ETHERS, ESTERS, & AMIDES)

4. CONDENSATION REACTIONS
These reactions synthesize new
functional group as a result of the
release of a water molecule
(condensation).
Condensation Reactions

5. involve 3 molecules…
a) Ethers
b) Esters
c) Amides
CONDENSATION REACTIONS

6. a) Ethers
When two hydroxyl groups react, an ether
group (C-O-C) bond is produced and
water is released.
H3C-OH + HO-CH3  H3C-O-CH3 + H2O
ETHERS

7. Structure of Ethers:
ETHERS

8. IUPAC naming system
i. The root of the chemical is the longer C-
chain
ii.The shorter C-chain and oxygen comprise
the ether side chain and is given the
ending “oxy”
iii.The location of the ether group is
numbered when necessary
ETHERS

9. Example #1
What is the IUPAC name for the
compound CH3-O-C2H5?
methoxyethane
ETHERS

10. Common naming system
This system uses the name “ether” as the
root and the alkyl names as prefixes.
CH3-O-C2H5
C2H5-O-C2H5
ethylmethyl ether
diethyl ether
ETHERS

11. Example #2
Write a balanced equation to show the
formation of an ether from propan-1-ol
only. Name the ether formed.
CH3CH2CH2OH + CH3CH2CH2OH 
H2SO4
CH3CH2CH2OCH2CH2CH3
+ H2O
1-propoxypropane
ETHERS

12. Example #3
ETHERS
Name the following ethers:
O
4-ethoxyhepta-2,5-diene
O
2-ethoxypentane

13. Properties of Ethers
Ethers have higher boiling points than their
hydrocarbon counterparts, but lower
boiling points than their alcohol
counterparts.
Ethers are usually effective solvents.
ETHERS

14. b) Esters
Esters (RCOOR’) are formed through the
condensation reaction between a hydroxyl
group and a carboxylic acid group.
CH3-OH + HOOCH3  CH3-OOCH3 + H2O
This condensation reaction is also known as
an esterification reaction.
Conc.
H2SO4
Heat
ESTERS

15. Structure of Esters:
ESTERS
R
C
O
R'
O

16. IUPAC naming system
i. The alcohol becomes the alkyl group.
ii.The carboxylic acid is the root, but the “-
oic acid” is changed to “-oate”.
ESTERS

17. Example #4
Name the reactants and identify and name
the products of the reaction.
CH3CH2CH2COOH + CH3CH2OH
butanoic acid ethanol
 CH3CH2CH2COOCH2CH3 + H2O
O
O
II
ethyl butanoate
Conc.
H2SO4
Heat
ESTERS

18. Example #5
Draw the structural diagram and write the IUPAC
name for the ester formed in the reaction
between propan-1-ol and benzoic acid.
-C-C-C-OH
H H H
H H H
H
l l l
l l l
C
C
C
C
C
C
H
H
H
H
H
C
HO
O
+
Conc.
H2SO4
Heat
C
C
C
C
C
C
H
H
H
H
H
C
O
O
-C-C-C-
H H H
H H H
H
l l l
l l l
propyl benzoate
ESTERS

19. ESTERS
H
H
C C
C
O
C
O
H3
HC
HC 3
3 ethyl 2-methylpropanoate1
2
3
2
It there are side chains attached to the carboxylic
acid part, then the side chain names are attached
to the ‘oate’ part of the ester name
Example #6

20. ESTERS
Example #8
Name the following molecules:
a) b)
O
O
pentan-2-yl ethanoate
1
2
3
4
5
1
2
2-methylpropyl ethanoate
1
2
3
1
2

21. Properties of Esters
Many aromatic fruits and flowers are due to
the natural production of esters. They are
also synthetically produced for foods
(tastes) and perfumes (odours).
Esters have a lower boiling point than their
carboxylic acid counterpoints.
ESTERS

22. c) Amides
Amides (RCONHR’) are produced due
to the condensation between a
carboxylic acid and an amine /
ammonia.
HCOOH + H-NH2  HCONH2 + H2O
AMIDES

23. Structure of Amides
AMIDES

24. IUPAC naming system
i. The amine becomes the alkyl group.
ii.The carboxylic acid is the root, but the “-
oic acid” is changed to “-amide”.
AMIDES

25. Example #9
Name the reactants and identify and name
the products of the reaction.
i. CH3COOH + NH3 
ii.CH3CH2CH2COOH + CH3NH2 
ethanoic acid ammonia
CH3CONH2 + H2O
CH3CH2CH2CONHCH3 + H2O
ethanamide water
butanoic acid methanamine
N-methylbutanamide water
AMIDES

26. Example #10
Redraw and name (IUPAC) the following
amides.
i. CH3CH2CH2CON(CH3)CH2CH3
ii.CH3CH2CH2CON(CH2CH3)2
N
O
ll
N-ethyl-N-methylbutanamide
N
O
ll
N,N-diethylbutanamide
AMIDES

27. Properties of Amides
Amides, just like amines, are generally
weak bases.
Generally, amides have low boiling points
and are not very soluble in water.
AMIDES

28. Properties of Amides
AMIDES
- Contain the peptide or amide linkage as their
functional group
- Structurally similar to esters
- Amide linkage is very significant in biological systems
as the forming and breaking of these bonds give
specificity to proteins