1. Organic Chemistry

2. Menu Lessons 1-11: Lesson 1 – Homologous Series Lesson 2 – Isomers
Lesson 3 – Meet the Families
Lesson 4 – Alkanes
Lesson 5 – Alkenes
Lesson 6 – Alcohols
Lesson 7 – Halogenoalkanes
Lesson 8 – Reaction Pathways
Lesson 9 – HL – Meet the Families (again)
Lesson 10 – HL – SN1 and SN2 Revisited
Lesson 11 – HL – More Nucleophiles

3. Menu Lessons 12-18: Lesson 12 – HL – Elimination Reactions
Lesson 13 – HL – Condensation Reactions
Lesson 14 – HL – Condensation Polymerisation
Lesson 15 – HL – Geometric Isomerism
Lesson 16 – HL – Optical Isomerism
Lesson 17 – HL – More Reaction Pathways

4. Lesson 1
Homologous Series

5. Overview
Copy this onto a double-page spread. You should add to it as a regular review throughout the unit.

6. Assessment This unit will be assessed by:
A test at the end of the topic (75%)…
An internal assessment (25%)

7. We Are Here

8. Lesson 1: Homologous Series
Objectives:
Reflect on previous knowledge of organic chemistry
Understand the term ‘homologous series’
Conduct the fractional distillation of crude oil
Understand and use the variety of different types of formula used in organic chemistry

9. Organic Chemistry
Organic chemistry is the chemistry of carbon containing compounds.
From the very simple: methane
To the very complex: Haem B

10. Homologous Series
A homologous series is a family of compounds that differs only by the length of its hydrocarbon chain
Members share:
General formula
Chemical properties
Three such series are the:
Alkanes
Alkenes
Alcohols

11. Homologous Series and Boiling Points
What do you think will be the trend in melting/boiling points as you go down a homologous series?
Why?

12. Formulas
Draw the compound with the formula C4H8O

13. What did you get?
Clearly a molecular formula is not enough!

14. Types of Formula Empirical Formula C4H8O C4H8O
Molecular Formula C4H8O C4H8O
Full Structural Formula
Aka displayed formula
Condensed Structural Formula
Note the ‘=‘ used for the C=C double bond
Skeletal formula
Not required but v. useful
Used in data booklet for complicated structures
Do not use in exam answers!
CH2=CHCH2CH2OH CH2=C(CH3)CH2OH

15. Thinking About Formulas
Produce a table to summarise each of the formulas. Include columns for:
What they show
Pros
Cons
How you make them
Draw full structural, condensed structural and skeletal formulas for at least 5 of the C4H8O compounds (not the cyclic ones)

16. Key Points
Organic chemistry is the chemistry of carbon containing compounds
A homologous series is a family of organic compounds differing only by the length of their carbon chains
The melting and boiling point increases as you go down a homologous series
Displayed formulas show the unambiguous arrangement of atoms in a compound

17. Lesson 2
Isomers

18. We Are Here

19. Lesson 2: Isomers Objectives: Describe the term structural isomer
Draw a name the non-cyclic alkanes
Draw and name the straight-chain alkenes

20. Isomers
Compounds with the same molecular formula but different structural formula
The 20 different C4H8O compounds from last lesson are isomers of each other
These are all structural isomers
Same number of each atom, but bonded in a different order
You would have even more if you included geometric and optical isomers

21. Structural Isomers of the Alkanes
The (non-cyclic) alkanes have the general formula CnH2n+2
Draw full and condensed structural formulas for every isomer of every one of the alkanes up to n = 6
If you finish early, draw each as a skeletal formula

22. Did you get them all?

23. And skeletally

24. Naming Straight-chain alkanes
Suffix:
Tells us the functional group of the molecule
For alkanes it is ‘-ane’
Prefix:
Tells us the length of the longest carbon chain:
1 carbon: meth-
2 carbons: eth-
3 carbons: prop-
4 carbons: but-
5 carbons: pent-
6 carbons: hex-
Example 1: ethane
Example 2: butane:
Task: write in the names of the 4 straight chain alkanes next to your diagrams from last slide

25. Naming branched-chain alkanes
Start by naming the longest chain
Add extras to say the size of a branch, its position and how many of that branch
Branch Size:
1 carbon: methyl-
2 carbons: ethyl-
3 carbons: propyl-
Position:
Number the carbons in the longest chain
Choose numbers to minimise the total numbers used
Number of same branches
One branch – nothing
Two branches – di-
Three branches – tri-
Four branches – tetra-
Example 1: 2-methylpropane
Example 2: 2,3-dimethylbutane
Task: name the remaining alkanes

26. The straight-chain alkenes
Alkenes are the same as alkanes but have one C=C double bond.
The suffix for the alkene homologous series is ‘-ene’
Task: draw full structural and skeletal formulas for each of the straight-chain alkenes up to C6 and name them.
Do the branched ones as well if you have time
Hint: you need to state the position of the double bond, but only if there is the possibility of multiple isomers:
i.e. ‘but-2-ene’ or ‘hex-1-ene’ but only ‘ethene’ not ‘eth-1-ene’

27. Did you get them?

28. Key Points
Structural isomers have the same number of each atom but they are connected differently
When naming compounds
The longest carbon chain forms the prefix
The functional group tells you the suffix
Sometimes numbers need to be used to tell you where this functional group is
Side chains and other groups are named according to what they are, how many there are and their position

29. Lesson 3
Meet the Families

30. We Are Here

31. Lesson 3: Meet the Families
Objectives:
Meet and learn to recognise the 7 functional groups required for the SL course
Produce a mind-map summarising each of the homologous series

32. Functional Groups Table (landscape)
You need to research and produce a mind- map summarising the following functional groups:
Alkane
Alkene
Alcohol
Aldehyde
Ketone
Carboxylic acid
Halide/Halogenoalkane
Your table should have four columns including:
Name of functional group
General structural formula (use ‘R’ to signify a carbon chain)
Rules for naming them (including the position where relevant)
A named example
Relative volatility
Relative solubility in water
For alcohols and halides you should include a branch to explain the difference between 1o, 2o and 3o
You should also have a branch called ‘Other Functional Groups’ that just allows you to recognise the groups:
Amine
Ester
Benzene
If HL you should leave space for four more functional groups

33. Building Organic Compounds
Use molecular models to make any of the compounds mentioned in your mind-map:
Draw it (structural and skeletal)
Name it
Give it to a friend and challenge them to do the same
Only go up to 6 carbons
Only include branched-chains for the alkanes

34. Key Points
There are 7 functional groups we need to know in detail and 3 extra we need to be able to recognise
We will look at each in detail over the rest of the unit

35. Lesson 4
Alkanes

36. Your notes and mind-map must be ready for me to inspect.
Refresh
Reviewing Your Notes
You should spend 60 seconds reviewing your notes from last lesson before attempting this.
Your notes and mind-map must be ready for me to inspect.
The following is a computer-generated representation of the molecule, methyl 2- hydroxy benzoate, better known as oil of wintergreen.
Deduce the empirical formula of methyl 2-hydroxy benzoate and draw the full structural formula, including any multiple bonds that may be present…The computer-generated representation shown does not distinguish between single and multiple bonds.
Name all the functional groups present in the molecule. H C O

37. We Are Here

38. Lesson 4: Alkanes Objectives: Explain the stability of the alkanes
Observe the combustion of alkanes
Describe the free-radical substitution reactions of alkanes and its mechanism
Observe the free-radical substitution of hexane

39. Combustion of Alkanes The alkanes really don’t do much
Combustion is of one of two notable reactions (this is why we use them for fuels)
Complete combustion:
alkane + oxygen  carbon dioxide + water
Incomplete combustion:
Alkane + oxygen  carbon + carbon monoxide + carbon dioxide + water
The amounts of C, CO and CO2 will vary depending on conditions
Task: Observe the combustion of the gas from the gas taps (propane/butane mix) and of a small amount hexane (in spirit burners). Hold the end of a clean boiling tube just over the flame for 15 seconds, this will collect soot from the flame.
Record all observations clearly and try to account for them
Include balanced equations to describe the (complete) combustion

40. Why so boring stable?
There are at least two reasons why alkanes are so unreactive
Task: Think back to your knowledge of molecular structure, and look at the tables of bond-enthalpies in the data booklet to see if you can work out why.

41. Halogenation
Alkanes will undergo halogenation if reacted with a halide in the presence of u.v. light.
For example:
C2H6(g) + Cl2(g) CH3CH2Cl(g) + HCl(g)
ethane chloroethane
This reaction is an example of free radical substitution
u.v.

42. Radicals Radicals are species with unpaired electrons
They are crazy reactive
Halogens form radicals when hit by uv light of the right frequency:
Cl Cl•
The dot after the Cl represents the unpaired electron and tells us we have a radical
This process is called homolytic fission – the bond breaks equally with one electron going to each chlorine
Task: draw Lewis structures for the Cl2 molecule and each of the Cl• radicals
u.v.

43. Reaction Mechanism: Free Radical Substitution
Cl Cl•
Cl• + C2H6  C2H5• + HCl
C2H5• + Cl2  C2H5Cl + Cl•
Cl• + Cl•  Cl2
Cl• + C2H5•  C2H5Cl
C2H5• + C2H5•  C4H10
Initiation
Radicals formed by homolytic fission
Propagation
These steps feed each other the radicals needed to continue
Termination
Any two radicals can combine to terminate the reaction
Concentration of radicals is low so this is a rare event
u.v.
A single radical can cause thousands of cycles of the propagation stage before it reaches termination
This same mechanism applies to all of the halogens
The alkane can be substituted multiple times, until every H has been replaced

44. Key Points Alkanes are unreactive
They release a lot of energy on combustion, and are easy to handle which makes them good fuels
Undergo free radical substitution to form halogenoalkanes and a hydrogen halide in the presence of UV light

45. Lesson 5
Alkenes

46. We Are Here

47. Lesson 5: Alkenes Objectives:
Describe the main addition reactions of the alkenes
Extract an alkene from a citrus fruit

48. Reactivity of Alkenes
Alkenes are considerably more reactive than alkanes and are a major industrial feedstock
The reactivity is due to the double bond:
The double bond contains 4 electrons
This is a significant amount of charge which:
Makes it attractive to electrophiles
Enables it to polarise approaching molecules
Most reactions of alkenes are addition reactions where two molecules come together to make one new one

49. Alkenes and hydrogen Alkene + hydrogen  alkane Reaction conditions:
Hot
Ni catalyst
This is an addition reaction, in which the hydrogen adds across the double bond

50. Alkenes and hydrogen halides
Alkene + hydrogen halide  halogenoalkane
Reaction conditions:
This reaction occurs very readily and needs no special conditions
This is an addition reaction, in which the hydrogen halide adds across the double bond

51. Alkenes and halogens Alkene + halogen  dihalogenoalkane
Reaction conditions:
This reaction occurs very readily and needs no special conditions
If the halogen used is an aqueous solution of bromine (bromine water), the orange-brown colour of bromine solution is decolourised.
This is the standard test for alkenes.

52. Alkenes and water Alkene + water  alcohol Reaction conditions:
Water must be steam
Phosphoric or sulphuric acid catalyst
This is the process used to make industrial ethanol
Fermentation from sugar would be far too expensive!

53. Polymerisation
Under the right conditions, alkene molecules will add to each other creating a polymer
In this case, 1-bromo-2-fluoroethene polymerises to form poly-1- bromo-2-fluroethene
Conditions:
Vary from alkene to alkene but often include high pressure, temperature and a catalyst
The carbons in the C=C double bonds form the carbon chain, everything else hangs off this chain

54. Drawing polymers Draw three-monomer lengths of the polymers formed by:
Propene
Styrene
Pent-2-ene

55. Key Points Alkenes undergo addition reactions with:
Hydrogen
Hydrogen halides
Halogens
Water (steam)
Alkenes undergo addition polymerisation
Alkenes are very economically important due to the range of products they can make

56. Lesson 6
Alcohols

57. We Are Here

58. Lesson 6: Alcohols Objectives:
Explain the relative ease of combustion of the alcohols
Describe the oxidation reactions of the alcohols
Investigate the oxidation reactions of the alcohols

59. Alcohols as Fuels
Alcohols combust more readily than equivalent alkanes but release less energy since they are already partially oxidised
Alcohol + oxygen  carbon dioxide + water
Alcohols are used as fuels:
As a fuel for cars – either pure or blended with petrol
Methanol as fuel for competitive motorsports including dragsters and monster trucks
Much fuel ethanol is fermented from crops…crops that could otherwise be eaten, forcing up food prices. Is this ok?

60. Oxidation of alcohols
The most important reactions of the alcohols are their oxidations
A range of compounds will oxidise them so the oxidiser is often represented as [O]
One oxidising agent you need to know is potassium dichromate, K2Cr2O7.
When using this, orange Cr (VI) is reduced to green Cr (III)
More on what this means in the oxidation and reduction unit
See next slide for details

61. Oxidation reaction scheme

62. Key Points Alcohols are highly combustible
Primary alcohols oxidise to form aldehydes, which oxidise to form carboxylic acids
Secondary alcohols oxidise to form ketones
Tertiary do not oxidise due to the 3 strong C-C bonds surrounding the –OH carbon

63. Lesson 7
Halogenoalkanes

64. We Are Here

65. Lesson 7: Halogenoalkanes
Objectives:
Describe the substitution reactions of halogenoalkanes with a strong base
Understand the SN1 and SN2 mechanisms for nucleophilic substitution
Produce an animation showing the two different mechanisms

66. Nucleophilic Substitution
One of the most important reactions undergone by halogenoalkanes is nucleophilic substitution
A nucleophile is a ‘nucleus-loving’ species that is attracted to positive charges.
Nucleophiles have either full negative charges or delta-negative charges
Water and hydroxide are both nucleophiles
In this case we can also call the reaction ‘hydrolysis’
The carbon in the carbon-halogen bond has a + charge due to the greater electronegativity of the halogen
This makes it susceptible to attack by nucleophiles

67. Halogenoalkanes and strong bases
A substitution reaction takes place, where the halogen atom is displaced by the hydroxide ion
halogenoalkane + sodium hydroxide  alcohol + sodium chloride
Conditions:
Aqueous base
Gently warmed (can at room temperature, but may be quite slow)
This is a nuclephilic substitution.
The C attached to the halogen is + due to the high electronegativity of the halogen
The OH- ion (our nucleophile) is attracted to the + carbon
A nucleophile is a species with a negative charge or a lone pair that is attracted to positive/delta-positive atoms

68. SN1 – Unimolecular nucleophilic substitution – animation here
Unimolecular because only one molecule is involved in the rate determining step
The rate determining step involves the spontaneous breaking of the carbon-halogen bond and is a heterolytic fission, forming a halide ion and a carbocation intermediate
The stability of the carbocation intermediate is a key factor in SN1
The attack by the nucleophile (OH-) is very fast, but does need the carbocation to be formed first
The rate is only dependent on the concentration of the halogenoalkane:
Rate = k[halogenoalkane]
Note: the curly arrows show the movement of pairs of electrons

69. SN2 – Bimolecular nucleophilic substitution – animation here
Bimolecular because two molecules are involved in the rate determining step
In the rate determining step, the nucleophile (OH-) attacks at the same time as the carbon-halogen bond breaks.
The reaction passes through a negative transition state where the carbon has a ‘half-bond’ to both the –OH and the –Br with an overall negative charge
The rate is dependent on both the concentration of the halogenoalkane and the nucleophile
Rate = k[halogenoalkane][nucleophile]

70. SN1 or SN2? 1o halogenoalkanes predominantly undergo SN2
2o halogenoalkanes undergo a mix of SN1 and SN2
3o halogenoalkanes predominantly undergo SN1
You do not need to know why at SL, but will find out more at HL

71. Refresh
Halogenoalkanes undergo substitution with strong bases to form alcohols
The reaction has two possible mechanisms:
SN1: the C-X bond breaks and then the nucleophile attacks
SN2: the nucleophile attacks at the same time as the C-X bond breaks
The mechanism depends on the halogenoalkane:
1o - SN2
2o - SN1 and SN2
3o - SN1