Alcohols, Acids, Esters

1
Alcohols, Acids, Esters

• R OH
• R COOH
• R COOR1

2
Functional Groups

• A group of atoms that give a characteristic set
  of properties to a molecule containing that group

3
Chloro Functional Group
Cl
4
Hydroxy Functional Group
OH
5
Carboxy Functional Group
O
C
OH
6
Alkyl Groups

• A fragment of an alkane that substitutes for a
  removed hydrogen atom

7
First 10 Alkyl Groups (R)

• CH3 methyl
• CH2CH3 ethyl
• (CH2)2CH3 propyl
• (CH2)3CH3 butyl
• (CH2)4CH3 pentyl

(CH2)5CH3 hexyl (CH2)6CH3
heptyl (CH2)7CH3 octyl (CH2)8CH3
nonyl (CH2)9CH3 decyl
8
First Four Chloroalkanes,

• CH3Cl chloromethane
• CH3CH2Cl chloroethane
• CH3(CH2)2Cl 1chloropropane
• CH3(CH2)3Cl 1 chlorobutane

9
First Four Alcohols

• CH3OH methanol
• CH3CH2OH ethanol
• CH3(CH2)2OH 1propanol
• CH3(CH2)3OH 1butanol

10
First Four Carboxylic Ccids

• HCOOH methanoic acid
• CH3COOH ethanoic acid
• CH3CH2COOH propanoic acid
• CH3(CH2)2COOH butanoic acid

11
The Need for Systematic Names

• To keep track of the many natural and synthetic
  organic chemicals
• Helps international communications of chemists
• Often common names do not relate to structure
  of the compound

12
Construction of Systematic Names

• The alkane or alkene chain
• Name and number of functional groups
• Position of functional groups on the carbon chain

13
Isomers

• Molecules of the same molecular formula but have
  their atoms arranged in a different way
• Butane above and Butene and above have isomers
• Chloroalkanes for example have isomers above
  chloropropane called structural isomers 

14
Isomers of C4H10
H
H
H
H
H
C C C C
H
butane
H
H
H
H
H
H
H
C
H
H
2 methyl propane or methyl propane
H
H
C C C
H
H
H
15
Isomers of Butene C4H8
H
H
H
H
H
C C C C
1 butene
H
H
H
H
H
H
C C C C
H
H
2 butene
H
H
H
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Isomers of Chloropropane
H
H
Cl
C C C
H
H
1 chloropropane
H
H
H
Cl
H
H
C C C
H
H
2 - chloropropane
H
H
H
17
Isomers of Propanol
H
H
OH
C C C
H
H
1 propanol
H
H
H
OH
H
H
C C C
H
H
2 propanol
H
H
H
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The Role of Shape in Chemical Reactions 

• Different structures of isomers can result in
  different properties and reactions
• eg. Starch and Glucose which are made up of long
  chains of glucose molecules
• Starch - we can digest uses a glucose
• Cellulose we cant cellulose ß glucose

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Glucose
a glucose
ß glucose
H
H
OH
H
C
HO
C
HO
C
C
HO
HO
C
C
H
OH
H
H
H
H
HO
HO
C
C
C
O
C
O
CH2OH
CH2OH
20
Substitution Reactions

• When one of the hydrogen atoms attached to a
  carbon atom is replaced by another atom or group
  of atoms
• Some examples follow

21
Production of Chloroethane
sunlight
CH3CH3 (g) Cl2(g) ? CH3CH2Cl (g)
HCl (g)
One Cl atom replaces, (or substitutes) an H atom
in the ethane molecule An example of a
substitution reaction
22
Production of Ethanol
CH3CH2Cl (g) OH (aq) ? CH3CH2OH
(aq) Cl(g)
One OH group replaces, (or substitutes) an Cl
atom in the chloroethane molecule. Sodium
Hydroxide solution is used Another example of a
substitution reaction
23
Production of Ethanoic Acid (Vinegar)

• Reaction with oxygen
• Natural reaction in air
• CH3CH2OH (aq) ? CH3COOH (aq)
• Reaction with an acidified catalyst
• Used in industrial applications
• CH3CH2OH (aq) ? CH3COOH (aq)

O2(aq)
MnO4(aq) orCr2O7 2(aq)
H(aq)
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Esters

• A group of organic compounds responsible for some
  of the natural and synthetic flavours ./ smells.
• Produced by adding an alcohol and a carboxylic
  acid
• Example of a condensation reaction a reaction
  where water is produced

25
Preparation of Esters(Esterfication)
O
O
C
R OH

C
H2O
R
OH
R
O
R
R R are hydrocarbon groups
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Preparation of Ethyl ethanoate

• Commonly called Ethyl acetate
• Gently heat a mixture of ethanol and ethanoic
  acid with a trace of sulfuric acid
• CH3COOH (l) CH3CH2OH(l) ? CH3COOCH2CH3 (l)
  H2O (l)

H2SO4(l)
O
O
H
H
H2SO4
H2O
C
C
C
C

CH3
CH3
OH
CH3
HO
CH3
O
H
H
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Preparation of Ethyl ethanoate
O
H
C
C

CH3
OH
CH3
HO
H
28
Preparation of Ethyl ethanoate
O
H
C
C

CH3
O
CH3
H
H
HO
29
Preparation of Ethyl ethanoate
O
H
C
C

CH3
O
CH3
H
H
HO
30
Preparation of Ethyl ethanoate
O
O
H
H
C
C
C
C

CH3
CH3
OH
CH3
HO
CH3
O
H
H
H2O
31
Naming Esters

• First part of the name comes from the alcohol
• Second part comes from the carboxylic acid
• Example
• Propanol added to Butanoic acid
• Gives Propyl Butanonoate

32
Polyester

• A copolymer made from alcohol and carboxylic
  monomers
• The alcohol has two hydroxy groups
• The acid has two carboxy groups
• The monomers join in a condensation reaction to
  form polyester chains
• Molecules held together with dispersion forces
  between molecules

33
Production of PET (PolyEthylene Terephthalate

• The most common polyester
• Made from
• Terephthalic acid
• Ethylene glycol

34
Production of PET (PolyEthylene Terephthalate
O
O
HO CH2 CH2 OH

HO C
C OH
Ethylene glycol
Terephthalic acid
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Production of PET (PolyEthylene Terephthalate
O
O
HO CH2 CH2 OH

HO C
C OH
Ethylene glycol
Terephthalic acid
O
O
O
O
O C
C O
O C
C O
CH2 CH2
H2O
Polyethylene terephthalate