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ORGANIC REACTIONS
5 Types of Reactions
1. Condensation Reactions
2. Addition Reactions
3. Substitution Reactions
4. Elimination Reactions
5. Oxidation Reactions
ORGANIC REACTIONS
CONDENSATION REACTIONS
(ETHERS, ESTERS, & AMIDES)
CONDENSATION REACTIONS
These reactions synthesize new
functional group as a result of the
release of a water molecule
(condensation).
Condensation Reactions
involve 3 molecules…
a) Ethers
b) Esters
c) Amides
CONDENSATION REACTIONS
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
Structure of Ethers:
ETHERS
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
Example #1
What is the IUPAC name for the
compound CH3-O-C2H5?
methoxyethane
ETHERS
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
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
Example #3
ETHERS
Name the following ethers:
O
4-ethoxyhepta-2,5-diene
O
2-ethoxypentane
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
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
Structure of Esters:
ESTERS
R
C
O
R'
O
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
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
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
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
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
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
c) Amides
Amides (RCONHR’) are produced due
to the condensation between a
carboxylic acid and an amine /
ammonia.
HCOOH + H-NH2  HCONH2 + H2O
AMIDES
Structure of Amides
AMIDES
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
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
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
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
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

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Tang 08 reactions intro (ethers, esters, amides) 2015

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