1. IB Organic Chemistry

2. Organic – What is it? Originally defined as the chemistry
of all living things
Now defined as the chemistry of carbon and its compounds
Includes
All biological molecules
Fossil fuels
Most synthetic materials
plastics

3. Homologous Series
There are so many organic molecules that we need a classification system
Homologous series : a family of like organic molecules
Members of the series have differing numbers of carbon atoms
Have similar characteristics and functional groups

4. Series: Alkanes Carbon chains that have only single bonds
Saturated hydrocarbons
Name ends in -ane
CnH2n+2
CH4
Methane
C2H6
Ethane
C3H8
Propane
C4H10
Butane
C5H12
Pentane

5. Naming: IUPAC This identifies the stem or root of the name
International Union of Pure and Applied Chemistry
Number of Carbons
Stem for IUPAC name 1
meth- 2
eth- 3
prop- 4
but- 5
pent- 6
hex-
Rule 1: Identify the longest straight or continuous chain of carbon atoms
This identifies the stem or root of the name

6. Examples
ethane
methane
hexane

7. Naming: IUPAC Rule 2: add a suffix based on the type of chain Type
Alkane
-ane
Alkene
-ene
Alkyne
-yne
Rule 2: add a suffix based on the type of chain
Alkanes have single bonds
Alkenes have double bonds
Alkynes have triple bonds
The location of the double or triple bonds need to be specified

8. Examples
1-propyne
propane
1-propene
2-butene

9. Naming: IUPAC
Rule 3: Name the side chains as the prefix of the name (label the carbon that it is located on)
Number of Carbons
Branch name 1
methyl- 2
ethyl- 3
propyl- 4
butyl- 5
pentyl- 6
hexyl-

10. Examples
2-methylhexane
3-ethyl, 3-methylpentane

11. Series: Alkenes Carbon chains that contain a double bond
Unsaturated hydrocarbons
Name ends in -ene
CnH2n
C2H4
Ethene
C3H6
Propene
C4H8
1-Butene
C5H10
1-Pentene

12. Series: Alkynes Carbon chains that contain a triple bond
Unsaturated hydrocarbons
Name ends in -yne
CnH2n-2
C2H2
Ethyne
C3H4
Propyne
C4H6
1-Butyne
C5H8
1-Pentyne

13. Functional Groups Alcohol Aldehyde Ketone Carboxylic acid Ester Halide
Groups attached to the carbon framework that give the molecule certain characteristics
Alcohol
Aldehyde
Ketone
Carboxylic acid
Ester
Halide

14. R-OH Series: Alcohols Functional Group: hydroxyl group, -OH
Name ends in -ol
CH3OH
Methanol
CH3CH2OH
Ethanol
CH3CH2CH2OH
1-Propanol
R-OH

15. Series: Carboxylic acids
Functional Group: carboxyl group, -COOH
Name ends in –oic acid
No numbers needed!
HCOOH
Methanoic acid
CH3COOH
Ethanoic acid
CH3CH2COOH
Propanoic acid
R-COOH

16. R-CHO Series: Aldehyde Functional Group: carbonyl group
Name ends in -al H
No numbers needed!
CH2O
Methanal
CH3CHO
Ethanal
CH3CH2CHO
Propanal
R-CHO

17. Series: Ketone Functional Group: carbonyl group Name ends in -one
Numbers needed when > 4 carbons
CH3COCH3
Propanone
CH3COCH2CH3
Butanone

18. R-COOR Series: Esters Functional Group: -COOR Name ends in –oate
Propyl ethanoate
CH3COOCH3
Methyl ethanoate
CH3COOCH2CH3
Ethyl ethanoate
CH3CH2COOCH3
Methyl propanoate
CH3CH2COOCH2CH3
Ethyl propanoate
R-COOR

19. R-X Series: Halides Functional Group: presence of halogen
Name – suffix stays the same
CH3CH2CH2Cl
1-chloropropane
R-X

20. C2H5 C4H10 CH3CH2CH2CH3 Types of Formulas Empirical Molecular
(simplest ratio)
Molecular
Full Structural
Condensed Structural
Line formula
C4H10
CH3CH2CH2CH3

21. Naming: IUPAC This identifies the stem of the name
International Union of Pure and Applied Chemistry
Number of Carbons
Stem for IUPAC name 1
meth- 2
eth- 3
prop- 4
but- 5
pent- 6
hex-
Rule 1: Identify the longest straight or continuous chain of carbon atoms
This identifies the stem of the name

22. Naming: IUPAC
Rule 2: Use the functional group ending as the suffix of the name (-ane, -ene, -yne, -ol, -al, -one, -oic acid, -oate)
Side chain
Prefix
-CH3
methyl
-C2H5
ethyl
-C3H7
propyl
-F, -Br, -I, -Cl
fluoro-, chloro-, iodo-, bromo-
-NH2
amino-
-OH
hydroxy-
Rule 3: Name the side chains as the prefix of the name (label the carbon that it is located on)

23. ID ONLY O CH3-O-CH2-CH3 methoxyethane (ether)
CH3—CH2—NH ethylamine (amine)
CH3—CH2—C—NH2 Propanamide (amide) O

24. Review Activity Part I Part II Part III
Come up with 10 names and 10 structures….
Place them in random order
Part II
Switch papers with someone else and solve
Part III
Check each others answers
Check another group’s answers if time…

25. Rings Add the word cyclo- to the stem Examples cyclopropane
cyclobutane
cyclopentane
cyclohexane

26. Aromatic Molecules
Contain the benzene ring
Unsaturated cyclohexene

27. Isomers
C4H10
Molecules that have the same kinds and numbers of atoms, but different arrangements
2-methylpropane
butane
CH3CHCH3
CH3CH2CH2CH3
CH3

28. Cis-Trans Isomers Alkenes Rotation at c-c double bonds restricted
cis = same side of double bond
trans = opposite sides

29. Primary, Secondary, & Tertiary
Primary carbon atoms: attached to functional group and 1 other carbon
Secondary carbon atoms: attached to the functional group and 2 carbons
Tertiary carbon atoms: attached to functional group and 3 other carbons

30. Activity Determine the strongest IMF present for:
Alcohols
halides
Ketones
Aldehydes
C. acids
alkanes
Determine the polarity. (high/medium/low)
Cut out and arrange your pieces by physical properties…

31. Physical Properties
Boiling point: As the carbon chain lengthens, the boiling point increases
Solubility:
Length of hydrocarbon chain:
chains are nonpolar
Solubility decreases as chain increases
Functional group: ability to form hydrogen bonds and interact with water
Alcohols, aldehydes, ketones, and carboxylic acids soluble
Halogenalkanes are not soluble in water

32. Halogenoalkanes… Very slightly soluble in water. Only slightly polar
Do not effectively break the hydrogen bonds between water molecules.
Soluble in nonpolar or less polar organic solvents such as alcohol and benzene .

33. Physical Properties
Volatility: ease of changing into the gaseous state
Chain length:
As the chain increases, the boiling point increases:
Smaller chains likely to be gases or liquids
Larger chains likely to be solids

34. Physical Properties Volatility Branching of the chain:
more branches = more space around the molecule = weaker IMFs = lower boiling points
Functional groups:
Polar groups have higher boiling points- stronger intermolecular forces- harder to break apart

35. Most volatile Least volatile Aldehyde Alkane Alcohol Ketone
Halogenoalkane
Aldehyde
Ketone
Alcohol
Carboxylic acid
Increasing boiling points
Increasing strength of intermolecular attraction

36. Alkane Reactivity Low reactivity! C-C and C-H bonds are very strong
Combustion
Complete produces carbon dioxide and water
Incomplete  limited oxygen – new products formed
Carbon monoxide (limited oxygen)
Carbon (extremely limited oxygen)

37. Alkane Combustion Carbon dioxide – greenhouse gas
Water – greenhouse gas
(absorb radiation and contribute to global warming)
Carbon monoxide – toxic to us
(absorbed by the body and bonds to hemoglobin preventing oxygen from being carried)
Carbon – particulates formed in the air, and is harmful to respiratory system

38. Cl2 + CH4  CH3Cl + HCl Alkane Reactivity
Substitution reactions – main type of reaction alkanes undergo
An incoming species takes the place of a H atom
Often called free radical substitutions
Cl2 + CH4  CH3Cl + HCl

39. Three Basic Steps in a Free Radical Mechanism
Chain initiation-
The chain is initiated by UV light breaking a chlorine molecule into free radicals.
Cl2  2Cl. 39

40. Homolytic Fission
Free radicals are formed if a bond splits evenly - each atom getting one of the two electrons. The name given to this is homolytic fission. 40

41. Three Basic Steps in a Free Radical Mechanism
Chain propagation reactions-
These are the reactions which keep the chain going
Have to have free radicals in the system to keep the chain going
CH4  +  Cl.  CH3.  +  HCl
CH3.  +  Cl2  CH3Cl  +  Cl . 41

42. Three Basic Steps in a Free Radical Mechanism
Chain termination reactions
These are reactions which remove free radicals from the system without replacing them by new ones – terminating the rxn
2 Cl.  Cl CH3. + Cl.  CH3Cl
CH3. + CH3.  CH3CH3 42

43. + H2  Alkene Addition Rxns Moves from unsaturated to saturated
Hydrogenation – addition of hydrogen on the double bond
Margarine is solid at room temperature because it has been hydrogenated and is saturated (higher melting points)
+ H2 

44. + Br2  Alkene Addition Rxns Halogenation: occur at room temperature
Accompanied by the loss of color of the reacting halogen
+ Br2 

45. + HBr  Alkene Addition Rxns
Hydrohalogenation: occur at room temperature
+ HBr 

46. + H2O  Alkene Addition Rxns Hydration
Addition of water turns the alkene into an alcohol Water splits into H and OH
+ H2O 

47. + H2O  Markovnikov’s Rule
Hydrogens add to the carbon that has the most hydrogens already!
+ H2O 

48. Polymers
Types of synthetic and natural polymers.

49. Polymerization of Alkenes
Alkene acts as the monomer (building block of a polymer)
Plastics are polymers of alkenes
polyethene
polypropene

50. Polymerization of Alkenes -PVC
Polymerization of chloroethene into polychloroethene
aka: PVC (polyvinylchloride)

51. Polymer Recycling Codes
Common household polymers

52. Polymers
The number code indicates the polymer type

53. Alcohols 2CH3OH(l) + 3O2(g) 2CO2(g) + 4H2O(g)
Increased solubility in water
CnH2n+1OH
Oxidation:
Complete oxidation: combustion reactions
Potassium Dichromate (VI)
2CH3OH(l) + 3O2(g) 2CO2(g) + 4H2O(g)

54. Alcohols
O and heat can be added to oxidize the OH group (in the form of Potassium dichromate VI)
Primary alcohols-oxidized to carboxylic acids
2ndary alcohols- oxidized to ketones
Tertiary alcohols- NR

55. Oxidation
Alcohols are oxidized to alkanals (aldehydes) or alkanones (ketones)

56. Oxidation: Primary Alcohols
Oxidizing agent:
Potassium dichromate VI
Ethanol is oxidized to ethanal
Can be further oxidized to ethanoic acid
Wine left exposed to air starts to smell of vinegar – this is the ethanoic acid

57. Oxidation: Secondary Alcohols
Propanol oxidized to propanone

58. Oxidation: Tertiary Alcohols
There is no hydrogen attached to the tertiary carbon. It is not possible for the tertiary acid to have a carbonyl group attached.

59. Primary Halogenoalkanes SN2 Mechanism
Substitution nucleophilic bimolecular
Bimolecular: depends on the concentration of both reactants (halogenoalkane and –OH)

60. Tertiary Halogenoalkanes SN1 Mechanism
Substitution nucleophilic unimolecular
Depends only on the concentration of the halogenoalkane
Steric hindrance caused by three alkyl groups around carbon
Bulky groups makes it difficult for an incoming group to attack the carbon atom

61. Tertiary Halogenoalkanes SN1 Mechanism
Both reactions involve heterolytic fission of C-Cl bond

62. Secondary Halogenoalkanes mechanisms
Secondary halogenoalkanes undergo a mixtures of SN1 and SN2 reactions, depending on reaction conditions

63. M&D questions
The structures of morphine and diamorphine (heroin) are shown in Table 20 of the Data Booklet. State the name of a functional group present in diamorphine (heroin) but not in morphine.

65. State the differences between the structures of morphine and diamorphine (heroin). State the names of all functional groups in the molecule of morphine.

66. Examples of strong analgesics are morphine, codeine and diamorphine (heroin).
Their structures are shown in Table 20 of the Data Booklet.
(i) Identify two functional groups present in all three of these analgesics.
(ii) Identify one functional group present in morphine, but not in diamorphine.

68. Identify two functional groups present in the side chain (R) of ampicillin by comparing its structure to that of penicillin in Table 20 in the Data Booklet.

71. ID ONLY O CH3-O-CH2-CH3 methoxyethane (ether)
CH3—CH2—NH ethylamine (amine)
CH3—CH2—C—NH2 Propanamide (amide) O

72. Objective: SWBAT demonstrate their knowledge of organic chemistry
Warm up: What is a homologous series?
Quiz today

73. Foldable… You need 5 sheets of paper
Separate them by about ½ to 1 inch
Fold and staple
Labels: Title: Homologous Series
Alkanes Ketones
Alkenes - Carboxylic acids
Alkynes - Esters
Alcohols - Halides
Aldehydes