1. Organic Chemistry: Introduction
IB Topic 10

2. 10.1 Introduction 10.1.1 Describe the features of a homologous series.
Predict and explain the trends in boiling points of members of a homologous series.
Distinguish between empirical, molecular and structural formulas.
Describe structural isomers as compounds with the same molecular formula but with different arrangement of atoms.
Deduce structural formulas for the isomers of non-cyclic alkanes up to C6.
Apply IUPAC rules for naming the isomers of the non-cyclic alkanes up to C6.

3. What is organic chemistry?
The study of carbon, the compounds it makes and the reactions it undergoes.
Over 16 million carbon-containing compounds are known.

4. What is organic chemistry?
Carbon
Carbon can form multiple bonds to itself and with atoms of other elements.
Carbon can only make four bonds since it has 4 valence electrons and most often bonds to H, O, N and S.
Because the C-C single bond (348 kJ mol-1) and the C-H bond (412 kJ mol-1) are strong, carbon compounds are stable.
Carbon can form chains and rings.

5. What is organic chemistry?
Hydrocarbons
Hydrocarbons are organic compounds that only contain carbon and hydrogen
Types of hydrocarbons include
Alkanes
Alkenes
Alkynes
Aromatic

6. 10.1.1 Describe the features of a homologous series.
A homologous series is a series of related compounds that have the same functional group.

7. Differ from each other by a CH2 unit
Can be represented by a general formula
examples:
CnH2n+2 (alkanes) or CnH2n (alkenes) or…

9. 10.1.1 Describe the features of a homologous series.
Watch out!!! Homologous compounds DO NOT have the same empirical formula!

10. Have similar chemical properties
Have physical properties that vary in a regular manner as the number of carbon atoms increases
Example: the alkanes

12. CnH2n+2 CnH2n # C Prefix Alkane (ane) Alkene (ene) 1 meth CH4 methane
ethene 3
prop 4
but 5
pent 6
hex

13. 10.1.2 Predict and explain the trends in boiling points of members of a homologous series.
What is the trend?
Why?
Alkane
Formula
Boiling Pt./oC
methane
CH4
-162.0
ethane
C2H6
-88.6
propane
C3H8
-42.2
butane
C4H10
-0.5
Intermolecular forces present & molar mass

14. Trends in boiling points of members of a homologous series (10.1.2)
Melting point and boiling point increase with more carbon atoms
Why?
intermolecular forces increase
adding a CH2 adds more electrons
this increases the Van der Waal’s forces
Alkane
Formula
Boiling Pt./oC
methane
CH4
-162.0
ethane
C2H6
-88.6
propane
C3H8
-42.2
butane
C4H10
-0.5
Intermolecular forces present & molar mass

15. Intermolecular forces present
Predict and explain the trends in boiling points of members of a homologous series.
Intermolecular forces present
Simple alkanes, alkenes, alkynes → van der Waals’ forces (nonpolar) → lower b.p.
Aldehydes, ketones, esters & presence of halogens (polar) → dipole: dipole forces → slightly higher b.p.
Alcohol, carboxylic acid & amine → hydrogen bonding (w/ O, N, F) → even higher b.p.
Naming song:

16. 10.1.2 Predict and explain the trends in boiling points of members of a homologous series.

17. Empirical Formula: Molecular Formula:
Distinguish between empirical, molecular and structural formulas.
Empirical Formula:
Smallest whole number ratio of atoms in a molecule
Molecular Formula:
Formula showing the actual numbers of atoms
Molecular Formula
Empirical Formula
CH4
C2H6
CH3
C6H12O6
C4H8
C8H16

18. 10.1.3 Distinguish between empirical, molecular and structural formulas.
Bond angles are drawn as though 90o. The true shape around C with 4 single bonds is tetrahedral and the angle is 109.5o.
Show every atom and every bond. Can use condensed structural formulas.
Hexane: CH3CH2CH2CH2CH2CH3 (condensed s.f.)
M.F. = C6H14 E.F. = C3H7

19. Structural formula Can use condensed structural formulas
bonds are omitted, repeated groups put together, side chains put in brackets
CH3CH2CH2CH2CH2CH3
or even CH3(CH2)4CH3
CH3CH(CH3)CH3

21. 10.1.3 Distinguish between empirical, molecular and structural formulas.

22. Skeletal formula
Not accepted in the IB for answers but often used in questions… cuz that’s how they do it
Every “corner” represents a carbon
Hydrogens are implied

23. Describe structural isomers as compounds with the same molecular formula but with different arrangement of atoms.
Structural isomers: compounds with the same molecular formula, but different arrangement of atoms
The Fuse School:

24. Describe structural isomers as compounds with the same molecular formula but with different arrangement of atoms.

25. Different isomers are completely different compounds
Have different physical properties such as melting point and boiling point

26. Structural Formulas for C4H10O Isomers

27. 10.1.5 Deduce structural formulas for the isomers of non-cyclic alkanes up to C6.
You should be able to draw out and write the structural formulas for all isomers that can be formed by:
CH4
C2H6
C3H8
C4H10
C5H12
C6H14
Eventually you should be able to name all isomers, as well

28. 10.1.5 Deduce structural formulas for the isomers of non-cyclic alkanes up to C6.
If there is a branch off of the main chain, put that formula in parentheses
CH3CH(CH3)CH3
CH3CH2CH2CH3

29. Monkeys Eat Peanut Butter
Apply IUPAC rules for naming the isomers of the non-cyclic alkanes up to C6.
Determine the longest carbon chain
Use the prefix (next slide) to denote the number carbons in the chain
Monkeys
Eat
Peanut
Butter 1
Meth- 2
Eth- 3
Prop- 4
But- 5
Pent- 6
Hex-

30. Use the suffix “-ane” to indicate that the substance is an alkane
Number the carbons in the chain consecutively, starting at the end closest to a substituent (groups attached to the main chain/most busy end)

31. 10.1.6 Apply IUPAC rules for naming the isomers of the non-cyclic alkanes up to C6.
Methylpropane
Methylbutane
Dimethylpropane

32. 1 Meth- 6 Hex- 2 Eth- 7 Hept- 3 Prop- 8 Oct- 4 But- 9 Non- 5 Pent- 10
Apply IUPAC rules for naming the isomers of the non-cyclic alkanes up to C6. 1
Meth- 6
Hex- 2
Eth- 7
Hept- 3
Prop- 8
Oct- 4
But- 9
Non- 5
Pent- 10
Dec-

33. name and number the location of each substituent
Apply IUPAC rules for naming the isomers of the non-cyclic alkanes up to C6.
For chains longer than 4 carbons with side chains:
name and number the location of each substituent
the name of the substituent will be written before the main chain and will end with “–yl” (or just memorize the below)
CH3 is methyl
C2H5 is ethyl
C3H7 is propyl

34. 10.1.6 Apply IUPAC rules for naming the isomers of the non-cyclic alkanes up to C6.
And with 2 or more side chains:
Use prefixes di-, tri-, tetra-, to indicate when there are multiple side chains of the same type.
Use commas to separate numbers and hyphens to separate numbers or letters.
Name the side chains in alphabetical order.
WHEW!!!!!!!!

35. How about C5H12? The isomers are:
Pentane methyl-butane 2,2-dimethyl propane

36. Nomenclature Practice
Name this compound 1
9 carbons = nonane 2 4 3 5 6 7 8 9
Step #1: For a branched hydrocarbon, the longest continuous chain of carbon atoms gives the root name for the hydrocarbon

37. Nomenclature Practice
Name this compound
9 carbons = nonane 1 2 4 3 5 6
CH3 = methyl 7
chlorine = chloro 8 9
Step #2: When alkane groups appear as substituents, they are named by dropping the -ane and adding -yl.

38. Nomenclature Practice
Name this compound
9 carbons = nonane 1 2 4 3 5 6
CH3 = methyl 7
chlorine = chloro 8 9 1 9
NOT 9 1
Step #3: The positions of substituent groups are specified by numbering the longest chain of carbon atoms sequentially, starting at the end closest to the branching.

39. Nomenclature Practice
Name this compound
9 carbons = nonane 1 2 4 3 5 6
CH3 = methyl 7
chlorine = chloro 8 9
2-chloro-3,6-dimethylnonane
Step #4: The location and name of each substituent are followed by the root alkane name. The substituents are listed in alphabetical order (irrespective of any prefix), and the prefixes di-, tri-, etc. are used to indicate multiple identical substituents.

40. What about boiling points of isomers???
Pentane methyl-butane 2,2-dimethyl propane

41. Magnitude of the force depends on…
Number of electrons and size of the electron cloud
with more electrons, valence electrons are farther away from the nucleus and can be polarized more easily
Shape of molecules
molecules with shapes that have more contact area have greater forces between them than those don’t

42. boiling point increases
these round shapes do NOT allow them to stick to one another
this flat shape allows it to stick to one another better
boiling point increases

43. 10.1 Introduction, cont.
Deduce structural formulas for the isomers of the straight-chain alkenes up to C6.
Apply IUPAC rules for naming the isomers of the straight-chain alkenes up to C6.
Deduce structural formulas for compounds containing up to six carbon atoms with one of the following functional groups: alcohol, aldehyde, ketone, carboxylic acid and halide.
Apply IUPAC rules for naming compounds containing up to six carbon atoms with one of the following functional groups: alcohol, aldehyde, ketone, carboxylic acid and halide.
Identify the following functional groups when present in structural formulas: amino (NH2), benzene ring ( ) and esters (RCOOR).
Identify primary, secondary and tertiary carbon atoms in alcohols and halogenoalkanes.
Discuss the volatility and solubility in water of compounds containing the functional groups listed in

44. 10.1.7 Deduce structural formulas for the isomers of the straight-chain alkenes up to C6.
Remember that structural formulas show the relative location of atoms around each carbon
Hexane: CH3CH2CH2CH2CH2CH3 (condensed s.f.)
M.F. = C6H14
Determine the molecular formulas for the alkenes below. Draw out and write the structural formulas for all isomers that can be formed by each.
C2H4
C3H?
C4H?
C5H?
C6H?

45. 10.1.8 Apply IUPAC rules for naming the isomers of the straight-chain alkenes up to C6.
Alkenes have a double bond between two or more of the carbons
CnH2n
Draw out and write the structural formulas for all isomers that can be formed by each
C2H4
C3H6
C4H8
C5H10
C6H12 45

46. 10.1.8 Apply IUPAC rules for naming the isomers of the straight-chain alkenes up to C6.
Suffix changes to “-ene”
When there are 4 or more carbon atoms in a chain, the location of the double bond is indicated by a number. Begin counting the carbons closest to the end with the C=C bond
Numbering the location of the double bond(s) takes precedence over the location of side chains
1-butene butene methylpropene 46

47. Naming the isomers (IUPAC) of straight chain alkenes up to C6 (10.1.8)
suffix changes to “-ene”
when there are 4 or more carbon atoms in a chain, the location of the double bond is indicated by a number
begin counting the carbons closest to the end with the C=C bond
numbering the location of the double bond(s) takes precedence over the location of any substituents
1-butene butene
but-1-ene but-2-ene

48. Count the number of carbons in a chain
Apply IUPAC rules for naming the isomers of the straight-chain alkenes up to C6. Breakin’ it down…
Count the number of carbons in a chain
Determine the ending of the name, based on # of bonds or functional group
Determine any side chains, which will be placed at the front of the name 48

49. choose the correct ending
Naming Practice!!!
choose the correct ending
ene

50. determine the longest carbon chain with the double bond
ene

51. assign numbers to each carbon
ene

52. assign numbers to each carbon
ene

53. attach prefix (according to # of carbons)
ene
1-hexene

54. determine name for side chains
ethyl
methyl
methyl
determine name for side chains
1-hexene
1-hexene

55. attach name of branches alphabetically
ethyl
methyl
methyl
attach name of branches alphabetically
2-ethyl-4-methyl-4-methyl-1-hexene

56. group similar branches
ethyl
methyl
methyl
group similar branches
2-ethyl-4-methyl-4-methyl-1-hexene

57. group similar branches
ethyl
methyl
methyl
group similar branches
2-ethyl-4,4-dimethyl-1-hexene
or 2-ethyl-4,4-dimethyl hex-1-ene

58. propene
2,4-dimethyl-2-pentene
2,4-dimethyl pent-2-tene
2-butene

59. a) 3,3-dimethyl-1-pentene b) sameC H 3 C H C C C H C H C H 3 3 C H 3
c) 4,5 dimethyl-2-hexene

60. Organic Chemistry Introduction: Functional Groups
Topic –

61. Deduce structural formulas for compounds containing up to six carbon atoms with one of the following functional groups: alcohol, aldehyde, ketone, carboxylic acid and halide.
Functional group: a group of atoms that defines the structure of a family and determines its properties
The functional group concept explained: The Chemistry Journey: The Fuse School:

63. Functional Group Formula Structural Formula
Apply IUPAC rules for naming compounds containing up to six carbon atoms with one of the following functional groups: alcohol, aldehyde, ketone, carboxylic acid and halide.
Functional Group
Formula
Structural Formula
Alcohol
-OH
- O – H
Aldehyde
-COH (on the end of a chain) O
- C – H
Ketone
-CO- (can’t be on end of chain)
- C –
Carboxylic Acid
-COOH (on the end of a chain)
- C – O – H
Halide
-Br, -Cl, -F, -I
- X

64. Functional Group Formula Suffix (or Prefix)
Apply IUPAC rules for naming compounds containing up to six carbon atoms with one of the following functional groups: alcohol, aldehyde, ketone, carboxylic acid and halide.
Functional Group
Formula
Suffix
(or Prefix)
Alcohol
-OH
-ol
Aldehyde
-COH (on the end of a chain)
-al
Ketone
-CO- (can’t be on end of chain)
-one
Carboxylic Acid
-COOH (on the end of a chain)
-oic acid
Halide
-Br, -Cl, -F, -I
bromo-,chloro-, fluoro-,iodo-

65. Know these 7, only have to recognize the 3 in the

66. Alcohols: suffix = “ol”
propan-1-ol
propan-2-ol
2-methyl propan-2-ol

68. Aldehydes: suffix = “al”
propanal
Note: an aldeyhde group is always on an end carbon so don’t need a number
butandianal

70. Ketones: suffix = “one”
propanone
(don’t need C#, must be in between two carbons)
butanone
2-pentanone or
pentan-2-one

71. butandione
pentan-3-one

73. Carboxylic Acids: suffix = “oic acid”
butanoic acid
Note: a carboxyl is always on an end carbon
propandioic acid

74. Halides: prefixes = “fluoro, chloro, bromo, iodo”
1-bromopropane
2-chlorobutane
1,2-diiodoethane
1,2-difluoroethene
1,1,2-trifluorothene

75. Only identify the following functional groups in structures: (10.1.11)
Formula
Amine
- NH2
Ester O
R – C – O – R
Benzene

76. amino, benzene ring, ester

77. A few more groups: Functional Group Formula Amine - NH2 Ester O
Identify the following functional groups when present in structural formulas: amino (NH2), benzene ring ( ) and esters (RCOOR).
A few more groups:
Functional Group
Formula
Amine
- NH2
Ester O
R – C – O – R
Benzene (phenyl-)
Ethyl ethanoate

78. Functional Groups

79. Identify each functional group by name… This is a possible idea for making flash cards.

80. Identify the following functional groups when present in structural formulas: amino (NH2), benzene ring ( ) and esters (RCOOR).
Esters are used for fragrances and flavoring agents since one of their major properties is smell
Benzene is in a family known as the aromatic hydrocarbons… because they smell 

81. Primary = carbon atom is only bonded to one other carbon
Identify primary, secondary and tertiary carbon atoms in alcohols and halogenoalkanes.
With reference to the carbon that is directly bonded to an alcohol group or a halogen:
Primary = carbon atom is only bonded to one other carbon
Secondary = carbon atom is bonded to two other carbons
Tertiary = carbon atom is bonded to three other carbons

82. Types of Carbon Atoms Primary carbon (1o) a carbon bonded to
one other carbon
Secondary carbon (2o)
two other carbons
Tertiary carbon (3o)
three other carbons

85. Secondary halogenoalkane Tertiary alcohol
Identify primary, secondary and tertiary carbon atoms in alcohols and halogenoalkanes.
Draw a…
Primary alcohol
Secondary halogenoalkane
Tertiary alcohol
What type are all aldehydes / carboxylic acids? Why?
What type are all ketones? Why?

86. Volatility: how easily a substance turns into a gas
Discuss the volatility and solubility in water of compounds containing the functional groups listed in
Volatility: how easily a substance turns into a gas
The weaker the intermolecular force, the more volatile it is
So, is a nonpolar or polar substance more volatile?
ionic › hydrogen bonding › dipole-dipole › van der Wall’s (Fig for reference)
Therefore, volatility:
vdW › d-d › H
alkane › halogenoalkane › aldehyde › ketone › amine › alcohol › carboxylic acid

88. Intermolecular forces present
Predict and explain the trends in boiling points of members of a homologous series.
Intermolecular forces present
Simple alkanes, alkenes, alkynes → van der Waals’ forces (nonpolar) → lower b.p.
Aldehydes, ketones, esters & presence of halogens (polar) → dipole: dipole forces → slightly higher b.p.
Alcohol, carboxylic acid & amine → hydrogen bonding (w/ O, N, F) → even higher b.p.
Naming song:

89. Solubility: a solute’s ability to dissolve in a polar solvent (water)
Discuss the volatility and solubility in water of compounds containing the functional groups listed in
Solubility: a solute’s ability to dissolve in a polar solvent (water)
The more polar a substance is, the more soluble it is
Solubility:
If the functional group is soluble (hydrogen bonded), it will be more soluble
Solubility decreases as chain length increases
Smaller alcohols, aldehydes, ketones & carboxylic acids are typically soluble
Halogenoalkanes are NOT soluble since they don’t form hydrogen bonds

90. Compare the boiling points of C2H6, CH3OH and CH3F
Discuss the volatility and solubility in water of compounds containing the functional groups listed in
Which substance is most soluble: ethene, propene, prop-1-ene or hex-1-ene?
Rank the following substances in order of increasing boiling point: C5H12, CH3CH2CH2CH2OH, CH3OCH2CH2CH3
Compare the boiling points of C2H6, CH3OH and CH3F
Explain, at the molecular level, why ethanol is soluble in water, but cholesterol (C27H45OH) and ethane are not.