Organic Chemistry

1
Organic Chemistry

• Chapter 22-23

2
Organic Chemistry

• Study of carbon-based compounds
• Carbon has 4 valence electrons
• Carbon always forms 4 covalent bonds
• Carbon compounds form chains and/or rings

3
Hydrocarbons

• Molecule or compound composed of carbon and
  hydrogen only
• Three Main Types
• Alkanes, Alkenes, Alkynes

4
Alkanes

• All single C-C bonds

H H H H H
H - C- C- C- C- C- H
H H H H H
H H H H H- C- C-
C- C- H H H H H
H H H H- C- C- C- H
H H H
C5H12
C4H10
C3H8
General Formula
CnH2n2
5
Alkenes

• At least one double CC bond

H H H H H
H - C- C- C- C C- H H
H H
H H H H H- C- C-
C C- H H H
H H H H- C- C C- H
H
C5H10
C4H8
C3H6
General Formula
CnH2n
6
Alkynes

• At least one triple CC bonds

H H H H - C- C-
C- C C- H H H H
H H H- C- C- C C- H
H H
H H- C- C C- H
H
C5H8
C4H6
C3H4
General Formula
CnH2n-2
7
Homologous Series

• Group of compounds with similar structure and
  function
• Table Q
• Members increase by one carbon and two hydrogens

8
Alkane Homologous Series
9
Alkene Homologous Series
10
Alkyne Homologous Series
11
Saturated vs. Unsaturated

• Saturated Hydrocarbons
• Contain only single Carbon to Carbon bonds
  (Alkanes)
• Unsaturated Hydrocarbons
• Contains at least one multiple (double, triple)
  Carbon to Carbon bond
• Alkenes and Alkynes

12
Naming Simple Hydrocarbons

• Name is based on two parts
• Number of carbons in longest continuous chain
  (Table P)
• Type of bonds between carbons
• Single ane
• Double ene
• Triple yne

13
Examples
H H H H H- C- C-
C- C- H H H H H

• Butane
• Pentane

H H H H H
H - C- C- C- C- C- H
H H H H H
14
Alkenes and Alkynes

• Name includes location of multiple bond
• Carbons numbered to give multiple bond the lowest
  possible number
• 1-butyne 2-butyne

H H H- C- C- C C- H
H H
H H
H- C- C C - C- H
H H
15
Chemical Formula

• Shows only number of each type of element
• C2H6
• C6H12O6

16
Structural Formula

• Shows how each atom is bonded to each other

H H H H H
H - C- C- C- C- C- H
H H H H H
H H H- C- C- C C- H
H H
17
Condensed Structural Formula

• Shows who is bonded to who, without the actual
  bonds

H H H H- C- C C- H
H
H H H H- C- C- C- H
H H H
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Branched Hydrocarbons

• Alkyl Group
• Hydrocarbon branch
• Branch name ends with -yl
• Location of branch is indicated by number
• Number carbons to give lowest possible number
• Multiple bond still takes priority in numbering

20
Examples
H H CH3 H H
H - C- C- C- C- C- H
H H H H H

• 3-Methyl Pentane
• 2-Methyl 1-Butene

H H- C- H
H CH2 H H- C- C C- H
H
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Functional Groups

• Specific arrangement of atoms that give compounds
  a unique property
• Table R
• Examples
• Hydroxyl Group, -OH O
• Carbonyl Group, - C -

?
23
Halides

• Halogen attached to a carbon
• Prefix indicates which halogen
• Table R
• for which carbon halogen is attached
• Multiple bonds still take priority in numbering

24
Halides
H H Cl H H- C- C-
C- C- H H H H H
Br H H H- C- C C- H
H
2-Chlorobutane
3-Bromopropene
CH3CH2CHClCH3
CH2BrCHCH2
25
Alcohol

• Hydroxyl group (-OH) attached to a carbon
• for which alcohol group is attached
• Name ends in ol
• Multiple bonds still take priority in numbering

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Alcohol
H H H H HO-
C- C- C- C- H H
H H H
H H H H H H
H - C- C- C- C- C- C- H
H H H OH H H
3-Hexanol
1-Butanol
CH3CH2CH2CH2OH
CH3CH2CH2CHOHCH2CH3
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Aldehyde

• Carbonyl group at end of chain
• Name ends with al
• Condensed structural formula ends with -CHO

O ? - C - H
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Aldehyde
H H O ? H- C- C- C- H
H H
H H H H O ?
H - C- C- C- C- C- H
H H H H
Propanal
Pentanal
CH3CH2CHO
CH3CH2CH2CH2CHO
29
Ketones

• Carbonyl group not on end of chain
• Number indicates which carbon the oxygen is
  attached to
• Name ends with one
• Condensed structural formula has -CO- in it

O ? - C -
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Ketones
H O H ? H- C- C- C- H
H H
H O H H H ?
H - C- C- C- C- C- H
H H H H
Propanone
2-Pentanone
CH3COCH3
CH3COCH2CH2CH3
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Amine

• Nitrogen attached to a carbon
• Number indicates which carbon the nitrogen is
  attached to
• Name ends in amine
• Multiple bonds still take priority in numbering

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Amine
H H H H
H2N- C- C- C- C- H
H H H H
H H H H H H
H - C- C- C- C- C- C- H
H H H NH2 H H
3-Hexanamine
1-Butanamine
CH3CH2CH2CH2NH2
CH3CH2CH2CHNH2CH2CH3
34
Amide

• Carbonyl group with an amine group attached to it
• Must be on an end
• Name ends in -amide

O H ? - C - N - H
35
Amide
H H O ? H- C- C- C- NH2
H H
H H H H O ?
H - C- C- C- C- C- NH2
H H H H
Propanamide
Pentanamide
CH3CH2CONH2
CH3CH2CH2CH2CONH2
36
Organic Acid
O ? - C - O - H

• Carbonyl group with a hydroxyl group attached to
  it
• Must be on an end
• Name ends in oic acid
• Condensed structural formula ends with -COOH
• Hydroxyl H is the acidic H

37
Organic Acid
H O ? H - C- C- OH
H
H H H O ? H - C-
C- C- C- OH H H H
Ethanoic Acid
Butanoic Acid
CH3COOH
CH3CH2CH2COOH
38
Ether

• Single oxygen between 2 carbon chains
• Name each carbon chain

H H H H
H- C- C-O - C- C- H
H H H H
H H H H H H
H - C- C- C- C- O- C- C- H
H H H
H H H
Diethyl Ether
Butyl Ethyl Ether
CH3CH2OCH2CH3
CH3CH2CH2CH2OCH2CH3
39
Ester
O ? - C - O -

• Carbonyl group with single oxygen between carbon
  chains
• Name in two parts
• 1st Branch off oxygen first as alkyl group
• 2nd Chain containing Carbonyl group
• Ending in oate

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Ester
H O H ? H
- C- O - C- C- H H
H
H H H O H H
? H - C- C- C- C- O- C- C- H
H H H
H H
Methyl Ethanoate
Ethyl Butanoate
CH3COOCH3
CH3CH2CH2COOCH2CH3
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Organic Reactions

• Saponification
• Fermentation
• Combustion
• Addition
• Substitution
• Polymerization (2 types)
• Esterification

43
Organic Reactions

• Saponification
• Production of Soap
• Fermentation
• Production of ethanol and CO2 from sugar
• C6H12O6 ? 2C2H5OH 2CO2

44
Combustion

• Complete Combustion of a Hydrocarbon
• CxHy O2 ? CO2 H2O
• Example
• C3H8 5O2 ? 3CO2 4H2O

45
Addition

• Addition of a halogen onto an alkene or alkyne

Br Br
H- C
C- H Br-Br ? H- C C- H
Br Br Br Br
H- C C- H
Cl-Cl ? H- C- C- H
Cl Cl
46
Substitution

• Substitution of one halogen in place of a
  hydrogen on an alkane

H H H H
H- C- C- H
Cl-Cl ? H- C- C- H H - Cl
H H
H Cl
H H Br H
H- C- C- H
Br-Br ? H- C- C- H H - Br
H Cl
H Cl
47
Polymerization

• Connecting of smaller pieces into a long
  repeating chain
• Plastics, starches, nylon
• Two types
• Addition
• Condensation

-(C2H4)n-
48
Addition Polymerization

• Double or triple bonds break to connect pieces
  together

H H H H H H H H

C-C C-C ? - C-C-C- C -
H H
H H H H H H
49
Condensation Polymerization

• Removal of water is used to link pieces together

H H H H
H H H H

H-O- C-C-O-H H- O- C-C-O-H ?
H-O-C-C-O-C-C-O-H H2O

H H H H
H H H H
50
Esterification

• Production of an Ester from an alcohol and acid
• Alcohol Acid ? Ester Water

H O H
O ?
? H- C- O - H H -O
-C -H ? H- C- O - C- H H2O

H H
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Isomers

• Two or more compounds with the same chemical
  formulas, but different structural formulas and
  properties
• Different Names

53
Isomer Example
C5H12
H H H H H
H - C- C- C- C- C- H
H H H H H
H H CH3 H H- C- C-
C- C- H H H H H
Pentane
Methyl Butane
H CH3 H H- C- C- C- H
H CH3 H
2,2-Dimethyl Propane
54
Isomer Example
C4H10O
H H H H HO-
C- C- C- C- H H
H H H
H H H H
H- C- C-O - C- C- H
H H H H
1-Butanol
Diethyl Ether
55
Isomer Example
C3H6O
H H O ? H- C- C- C- H
H H
H O H ? H- C- C- C- H
H H
Propanal
Propanone
56
Isomer Example
C3H6O2
H O H ? H
- C- O - C- C- H H
H
H H O ? H - C- C- C-
OH H H
Methyl Ethanoate
Propanoic Acid