1. Introduction to Organic Chemistry
Ritalin
methyl 2-phenyl-2-piperidin-2-ylacetate

2. Common Elements in Organic Compounds
24.1

3. Classification of Hydrocarbons
24.1

4. Classification of Hydrocarbons
Aromatic: a hydrocarbon that contains
one or more benzene rings.
24.1

5. Classification of Hydrocarbons
Aliphatic: Relating to organic compounds in which carbon atoms DON’T HAVE BENZENE RINGS
24.1

6. CH4 C2H6 C3H8 methane ethane propane
Alkanes have the general formula CnH2n+2 where n = 1,2,3,…
alkanes have only single covalent bonds
alkanes are called saturated hydrocarbons because they contain the maximum number of hydrogen atoms that can bond with the number of carbon atoms in the molecule. (unsaturated hydrocarbons = alkenes & alkynes)
CH4
C2H6
C3H8
methane
ethane
propane
24.2

7. Alkane Nomenclature – Counting to Ten
1 Meth
2 Eth
3 Prop
4 But
5 Pent
6 Hex
7 Hept
8 Oct
9 Non
10 Dec

8. Structural isomers are molecules that have the same molecular formula but different structures
24.2

9. How many structural isomers does pentane, C5H12, have?
n-pentane C H
CH3
2,2-dimethylpropane
2-methylbutane
24.2

10. Alkane Nomenclature
The parent name of the hydrocarbon is that given to the longest continuous chain of carbon atoms in the molecule.
CH3
CH2 CH
4-methylheptane 1 2 3 4 5 6 7
An alkane less one hydrogen atom is an alkyl group.
CH4
methane
CH3
methyl
24.2

11. Alkane Nomenclature Names of Common Substituent Groups
Functional Group Name
-F fluoro
-Cl chloro
-Br bromo
-I iodo
-NO2 nitro
-OH hydroxyl (alcohol)
-CH3 methyl
-CH2CH3 ethyl
-CH2CH2CH3 propyl
-CH2CH2CH2CH3 butyl
-NH amine
-N=O amide

12. When one or more hydrogen atoms are replaced by other groups, the name of the compound must indicate the locations of carbon atoms where replacements are made. Number in the direction that gives the smaller numbers for the locations of the branches.
CH3 CH
CH2 1 2 3 4 5
CH3
CH2 CH
2-methylpentane 1 2 3 4 5
4-methylpentane
24.2

13. When one or more hydrogen atoms are replaced by other groups, the name of the compound must indicate the locations of carbon atoms where replacements are made. Number in the direction that gives the smaller numbers for the locations of the branches.
CH3 CH
CH2 1 2 3 4 5
CH3
CH2 CH
2-methylpentane 5 4 3 2 1
2-methylpentane
24.2

14. When one or more hydrogen atoms are replaced by other groups, the name of the compound must indicate the locations of carbon atoms where replacements are made. Number in the direction that gives the smaller numbers for the locations of the branches.
CH3 CH
CH2 1 2 3 4 5
CH3
CH2 CH
2-methylpentane 1 2 3 4 5
4-methylpentane
24.2

15. Alkane Nomenclature Prefixes: di means double tri means triple
Use prefixes di-, tri-, tetra-, when there is more than one alkyl branch of the same kind.
CH3 CH
CH2 1 2 3 4 5 6
2,3-dimethylhexane
CH3
CH2 C 1 2 3 4 5 6
Prefixes:
di means double
tri means triple
tetra means quadruple
3,3-dimethylhexane
24.2

16. Use previous rules for other types of substituents.
Alkane Nomenclature
Use previous rules for other types of substituents.
CH3 CH Br 1 2 3 4 Cl
Names of Common Substituent Groups
Functional Group Name
-F fluoro
-Cl chloro
-Br bromo
-I iodo
-NO2 nitro
2-bromo-3-chlorobutane
CH2 CH
CH3 Br 1 2 3 4 F
1-bromo-3-fluorobutane
24.2

17. Yes, the groups (branches) need to be listed alphabetical!
What is the IUPAC name of the following compound?
methyl
branch
ethyl
branch
CH3 CH
CH2
CH2CH3 1 2 3 4 5 6 7 8
…octane
4-ethyl-2-methyloctane
Yes, the groups (branches) need to be listed alphabetical!
What is the structure of 2-chloro-4-methylhexane?
CH3 CH
CH2 Cl 1 2 3 4 5 6
24.2

18. Summary of rules for naming a basic alkane:
Assign a parent name based upon the longest continuous Carbon chain.(Find the longest C chain)
Assign location numbers (called locants) to all of the groups. Count along the parent chain in both directions: use the version that yields the lowest starting locant for the first branch.
Identify and name the branches coming off the parent chain.
Have same groups in different places? Use prefixes. (di for two, tri for three, or tetra for four)
Shove it all together alphabetically using commas and dashes!

20. Now build n-heptane

21. Draw the line angle formulas for:
pentane
butane
decane
hexane

22. the condensed structural formula
Practice Makes Perfect! Build this model (one model per table group), and write down the name.
This drawing is called
the condensed structural formula
CH3
CH2 CH Br
Locants
3-bromo-2,4-dimethylhexane

23. the condensed structural formula
This drawing is called
the condensed structural formula
CH3
CH2 CH Br
Locants
The “complete structural formula” shows all the H bonds too.
3-bromo-2,4-dimethylhexane Br
This drawing is called
The line-angle formula 1 5 3 6 4 2
3-bromo-2,4-dimethylhexane
Hold up your model and position it so that it
looks like the line-angle formula. Do you see
why it is drawn like this now?

24. Build this model then name it.
CH3 Br Cl
Locants Br
5,6-dibromo-7-chloro-4-ethyl-2-methylnonane

25. Draw 2-bromo-4-ethyl-3-methylheptane
Draw 1-chloro-4,4-diethyloctane
See white board for answers

26. As I stamp your homework, build mirror images of these models:
Part 1) CH2BrCl
Part 2) CHBrClF
We will use these to discuss chirality.

27. Isomers of heptane
Heptane
2-Methylhexane
3-Methylhexane
2,2-Dimethylpentane
2,3-Dimethylpentane
2,4-Dimethylpentane
3,3-Dimethylpentane
3-Ethylpentane
2,2,3-Trimethylbutane
Please put poster on middle lab table
CH2BrCl
CHBrClF
I NEED 2 of each built

28. CH2BrCl
Optical
Isomers
CHBrClF
achiral
Chiral
(Handedness)
24.2

29. not not superimposable on its mirror image
video
Achiral
(NOT Handedness)
Chiral
(Handedness)
24.2

30. In the 1960’s, a drug called thalidomide was widely prescribed in the Western Europe to alleviate morning sickness in pregnant women.
effective medication
causes birth defects

31. Alkanes whose carbon atoms are joined in rings are called cycloalkanes
Alkanes whose carbon atoms are joined in rings are called cycloalkanes. They have the general formula CnH2n where n = 3,4,…
24.2

32. Alkenes have the general formula CnH2n
contain at least one carbon-carbon double bond
CH2 CH
CH3
CH3 CH
1-butene
2-butene C Cl H C Cl H
cis-dichloroethene
trans-dichloroethene
24.2

33. CH2
CH3 CH
1-hexene
CH2
CH3 CH
2-hexene CH
CH3
CH2
2-hexene

34. Alkynes have the general formula CnH2n-2
contain at least one carbon-carbon triple bond
CH3 C CH C
CH2
CH3
1-butyne
2-butyne
24.2

35. Aromatic Hydrocarbons
24.3

36. Aromatic Compound Nomenclature1 2 3 4 5 6
1- Number the benzene ring in the way that provides the lowest numbering system.
2- Identify the groups on benzene. If only one group is present, a number is not required (it is assumed to be located at #1)
3- Follow all naming rules for alkanes.

37. Aromatic Compound Nomenclature
aminobenzene
ethylbenzene
NH2
CH2CH3 Cl
NO2
nitrobenzene
chlorobenzene Br Br Br 1 2 3 4 5 6
1,2-dibromobenzene
1,2,4-tribromobenzene
1,3-dibromobenzene
24.3

38. Model naming practice
1,3,3-tribromo-7-fluoro-6,6,7,8-tetramethyl-4-decyne

39. Organic Chemistry: Other Functional Groups
21/10/99
Organic Chemistry: Other Functional Groups

40. 21/10/99
Functional groups
Functional groups are parts of molecules that result in characteristic features
About 100 functional groups exist, we will focus on about 10

41. Hydroxyl, carbonyl, carboxyl
21/10/99
Hydroxyl, carbonyl, carboxyl
There are other names that describe patterns of atoms that are parts of functional groups.
“Hydroxyl” refers to –OH
“Carbonyl” refers to C=O
“Carboxyl” refers to COOH

42. Alcohols contain the hydroxyl functional group and have the general formula R-OH. OH or HO is stuck onto a Carbon chain of some sort.
“R” means the Rest of the compound in that direction.
24.4

43. Alcohols – OH replaces an a H
R-OH
R group = CH3, C2H5 , C3H7 , etc. (some sort of carbon chain/ring)
Which compound shown is an alcohol ?

44. How Do You Name Alcohols ?
Count the carbons and write the alkane name it would be then drop the “e” and replace with “ol”
Name the following:
Ethane
Ethanol Ethanol
Propanol

45. How Do You Name Alcohols ?
Special Note: If the OH is not on an end carbon, you must identify the locant of the carbon before the name.
2-Propanol
2-Butanol

46. Ethers have the general formula R-O-R’.
Condensation Reaction (not on exam)
CH3OH + HOCH CH3OCH3 + H2O
H2SO4
catalyst
24.4

49. Ethers – a bad smelling compound, used to put people to sleep.
General formula: ROR'
Example:
-O- is in the middle of carbon chain (breaks up the chain of C’s)
Naming: Name the groups on each end (O is the middle) and add “ether“. If the same group appears twice use di in front of name.
Dimethyl ether

50. Using ethers on someone is a CRIME!
You better pray for ROR.

51. For exam: You will need to identify and name ethers
diethyl ether
ethyl methyl ether

52. Esters – compounds that smell like fruit (sometimes), come from a reaction between an alcohol and an acid.
General Formula - RCOOR
Example- CH3COOC2H5
CH3COOC2H5
(Aunt Ester is a COOC and smells like fruit (apples, bananas, apricot, etc.)
My Aunt Ester is COCO!
Aunt Ester is bananas and smells like them too! O C C C O

53. Naming Esters: Name the alkane parent, drop the “e”, replace with “oate” then name the branch that the is after the =O but you write it first. Simple! Right?
Methyl butanoate
C3H7COOCH3
Methyl Butanoate
C2H5COOC2H5
Ethyl Propanoate
Ethyl propanoate

54. Carboxylic acids (also called organic acids) contain the carboxyl ( -COOH ) functional group.

55. Carboxylic/ Organic Acids –(Contain a COOH in place of an H)
To name organic acids: Count all the carbons to get the base alkane, drop the “e” and replace with “oic”
Name the following:
Propanoic Acid

56. Name the Following
Butanoic Acid
Methanoic Acid

57. Aldehydes vs. Ketones
Ketone
Aldehyde

58. How do you name Aldehydes and Ketones?
1. Decide if its an Aldehyde or Ketone
2. Count all the carbons and write the base Alkane name, drop the “e” and replace with “one” for ketones or ”al” for aldehydes.
Propanone
Ketone

59. Name the following:
Propanal
Butanone

61. Functional Group Chemistry
Amines are organic bases with the general formula R3N.
*Has a nitrogen on the chain somewhere.
What else could this classified as?
Right! Carboxylic acid!
FYI: It’s an amino acid!

62. Functional Group Chemistry
Amides are organic compounds that contain R-C(O)NH2
is a carbon chain
contains Nitrogen
right next to it must be a double bonded O to C C=O

63. See your handout

64. 24.4

65. Got it?
Which one is an alcohol?

66. Got it?
Which one is a ketone?

67. Got it?
Which one is an aldehyde?
NONE!

68. Got it?
Which one is an organic acid?

69. Got it?
Which one is an ester?
NONE!

70. Got it?
Which one is an ether?

71. Name each compound in the following reaction.
Practice Questions
Type of compound?
CH3OCH3
Named: Dimethyl Ether
CH3CH2CH2COOH
Named Butanoic Acid (Carboxylic/Organic acid COOH)
Name each compound in the following reaction.
CH3OH+ C2H5COOH HOH + C2H5COOCH3
Methyl Propanoate
(is an ester)
Methanol
Propanoic Acid
Water

72. 1 Meth; 2 Eth; 3 Prop; 4 But; 5 Pent
Alkane Nomenclature
What is happening with this chart and why?
1 Meth; 2 Eth; 3 Prop; 4 But; 5 Pent
6 Hex; 7 Hept; 8 Oct; 9 Non; 10 Dec
24.2

73. Hydroxyl, carbonyl, carboxyl
21/10/99
Hydroxyl, carbonyl, carboxyl
Q: which functional groups contain a hydroxyl group? A carbonyl group? A carboxyl group?
Hydroxyl: alcohols, carboxylic acids.
Carbonyl: aldehydes, ketones, carboxylic acids, amides, esters.
Carboxyl: carboxylic acids
Note that properties such as boiling and melting point change due to functional groups

74. Name the following compounds
Ethanol (alcohol)
Methanal (aldehyde)
2-Propanone (ketone)

75. Identify the functional groups
Ethanoic Acid
(Carboxylic acid)
Dimethyl Ether (Ether)
Methyl butanoate
(ester)
C3H7COOCH3

76. How to name amines/amides
Count parent carbon chain
Assign locant to amine (lowest #)
Name of a normal hydrocarbon
Drop “e”
Add “amine”
Put locant in front
Amides
Count parent carbon chain
Name of a normal hydrocarbon
Drop “e”
Add “amide”

79. Do now: Summarize your Organic notes onto one page.
You will be making a poster next week for the entire unit.
Alkanes, alkenes, alkynes, cyclo and benzene containing compounds, & all functional groups.
Drawing, identifying, and naming.
When done, work on practice worksheets.
Stamp 1: ANE ENE YNE PRACTICE
Stamp 2: ORGANIC PRACTICE 3

80. 1 meth
2 eth
3 prop
4 but
5 pent
6 hex
7 hept
8 oct
9 non
10 dec
Alkane – single bonds
Alkene – double bonds
Alkyne – triple bonds
Cyclo – chained ring (The above are all aliphatic)
Benzene – special ring
(has 6 carbons in an alternating double/single bond set up. The only aromatic type.)

81. ORGANIC PARTNER POSTER
Intermolecular Forces (IMFs)
To be discussed in later unit