1. What is Organic Chemistry?
The study of CARBON and compounds that contain carbon!
Carbon with 4 valence electrons is able to form four covalent bonds with other carbon atoms and other kinds of atoms.

2. Carbon Bonding Forms compounds by covalent bonding
single bond - one shared pair of electrons
double bond - two shared pairs of electrons
triple bond - three shared pairs of electrons

3. Carbon Bonding

4. Characteristics of Organic Compounds
1. Generally non-polar 2. Non-electrolytes 3. Have low melting points due to weak intermolecular forces

5. Hydrocarbons These compounds are composed of only hydrogen and carbon
Homologous series - group of organic compounds with similar properties and related structures

7. Alkanes Hydrocarbons with the formula CnH2n+2 (Table Q) end in “ANE”.
All alkanes have all SINGLE bonds and are saturated hydrocarbons.

8. Alkanes Example #1: Methane Meth = 1 carbon -ane = alkane
CnH2n+2  C1H2(1)+2  CH4 (molecular formula)
Example #2: Ethane
Eth = 2 carbons
CnH2n+2  C2H2(2)+2  C2H6

9. Drawing Alkanes
Remember that each carbon requires 4 bonds surrounding it.
Rules for drawing alkanes:
Build your carbon atom “backbone”
Place 4 bonds around each carbon atom.
Fill in the hydrogens
Check your molecular formula with your structural formula.

10. Drawing Alkanes Octane – C8H18 – C – C – C – C – C – C – C – C –
Condensed Formula:
CH3CH2CH2CH2CH2CH2CH2CH3
Can you figure out how the condensed formula was written based on the structural formula for octane?

11. Practice
Draw structural diagrams and condensed formulas for hexane, ethane and propane

12. Naming Organic Compounds
When naming any organic compound, it
is crucial that you count using the
longest chain of carbons
Example:
C – C – C – C
C – C
hexane
CH3
C – C – C – C – C – C – C – C – C – C
decane
So what about these
Other carbons?????

13. Naming Branches (Side Chains)
Branches are also called side chains.
Name the longest chain and draw a line through all the carbons in the chain.
Box off the side chains that are left over.
Name the Alkyl Group whose ending is “yl” to show a side chain.

14. Alkyl Group (side chains)
Alkyl structures have one less hydrogen than the corresponding alkane.
Side Chain Length
In Carbons
Name
Side chain name
Alkyl Formula
CnH(2n+2 -1) 1
meth
methyl
CH3 2
eth
ethyl
C2H5 3
prop
propyl
C3H7 4
but
butyl
C4H9 5
pent
pentyl
C5H11 6
hex
hexyl
C6H13

15. Naming Side Chains Numbering left to right:
Determine which carbon of the longest chain the side chain is attached to using the smallest number
Put that number with a dash in front of the side chain name.
STEP 1:
Numbering left to right:
C – C – C – C – C – C
CH3
the side chain is on the #4 carbon of hexane

16. STEP 2
Numbering right to left : ←
C – C – C – C – C – C
CH3
the side chain is on the #3 carbon of hexane
3 is lower than 4, so we use 3 and name this:
3-methylhexane

17. Isomers
Organic compounds that have the same molecular formula, but different structural formula.
The more carbons in the structure, the more isomer variations that are possible.
Butane
2-methylpropane

18. Examples Example: One isomer of hexane is
2-methylpentane. Please draw both below:
Hexane (C6H14)
2-methylpentane (C6H14)

19. Draw nonane and then draw and name 1 isomers of nonane.

20. Which pair of compounds are isomers? Support your answer.
A) P2O5 & P4O10
B) CH3OCH3 & C2H5OH
C) NO2 & N2O4
D) HCOOH & CH3COOH

21. Which structural formula represents a molecule that is not an isomer of pentane? Support your answer

22. Which formula represents
an unsaturated hydrocarbon?
Support your answer.
A) C5H14
B) C5H8
C) C3H8
D) C2H6

23. Which formula represents a hydrocarbon? Support your answer.
A) CH3CH2CH2CH3
B) CH3CH2COOCH3
C) CH3CH2CH2COOH
D) CH3CH2CH2CHO

24. Alkenes Hydrocarbons with the formula CnH2n (Table Q) end in “ENE”.
All alkenes have at least one DOUBLE bond (C=C) and are considered unsaturated hydrocarbons.

25. Naming Alkenes 3-heptene
Since the double bond in an alkene can be anywhere, we must assign a number to indicate where it is to be placed.
We use the same principle of smallest numbers, and so the double bond is named for the smallest numbered carbon it comes after.
Example: C – C – C = C – C – C – C
3-heptene

26. If the double bond is after the first carbon, we name it n-pentene
– C – C – C - C – C – C = C
If the double bond is after
the first carbon, we name it
n-pentene

27. Alkynes Hydrocarbons with the formula CnH2n-2 (Table Q) end in “YNE”.
All alkynes have at least one TRIPLE bond (CΞC) and are also considered unsaturated hydrocarbons.

28. Naming Alkynes
The rules for naming alkynes is the same as naming alkenes with respect to the numbering on where the triple bond is placed.
Example: C – C – C – C Ξ C – C
2-hexyne
If the triple bond comes after the first Carbon then use n-
3 smaller than 4

29. Functional Groups (Table R)
Not all organic compounds are hydrocarbons!!
Different functional groups cause compounds to have different physical and chemical properties!!

30. Hints for the Classes of Organic Compounds
Alcohol …….COH
Aldehyde……CHO
Ketone….COC
Organic Acid……COOH
Ester……..COO (ESTER SINGS COO)
Amine/Amide…..Look for N

31. Functional Groups: Physical Properties
Boiling Point/Melting Point
The greater the # of carbons in carbon chain, the higher the boiling point/melting point!
If compounds have the same # of carbons: the branched molecules have a higher boiling and melting point than the linear molecules.

32. Prefixes are: fluoro, chloro, bromo, or iodo
Halides
one or more halogens (group 17) attached to one carbon atom or chain of carbon atoms.
Prefixes are: fluoro, chloro, bromo, or iodo

33. H Br H H H – C – C – C – C – H H H H H 2-bromobutane
Halides – Example #1
H Br H H
H – C – C – C – C – H
H H H H
2-bromobutane

34. Halides – Example #2
H H Cl H H H H – C – C – C – C – C – C – H H H H H H H Name this halide.

35. Halides – Example #3
H Br F H H
H – C – C – C – C – C – H
H H H H H
Name this halide.

36. Halides – Example #4
H Cl Cl H H H
H – C – C – C – C – C – C – H
H H H H H H
Name this halide.

37. Halides Draw the following halides. 1,2,4-triflouroheptane
2-bromopropane
1,3-diiodobutane

38. Alcohols
A hydrogen atom of a hydrocarbon is replaced by an -OH group (hydroxyl group).
When naming alcohols, drop the “e” and add “ol”.

39. Alcohols – Example #1 H H │ │ H ─ C ─ H H ─ C ─ OH H H
Methane Methanol
H H
│ │
H ─ C ─ H H ─ C ─ OH
H H

40. H H OH │ │ │ H ─ C ─ C ─ C ─ H │ │ │ H H H Name the alcohol.
Alcohols – Example #2
H H OH │ │ │ H ─ C ─ C ─ C ─ H │ │ │ H H H Name the alcohol.
This is a primary alcohol :
the carbon attached to the OH is
attached to one other carbon.

41. H H H │ │ │ H ─ C ─ C ─ C ─ H │ │ │ H OH H Name the alcohol.
Alcohols – Example #3
H H H │ │ │ H ─ C ─ C ─ C ─ H │ │ │ H OH H Name the alcohol.
This is a secondary alcohol: the
carbon attached to the OH is also
attached to two other carbons.

42. Alcohols – Example #4 Name the alcohol.
H OH H H H │ │ │ │ │ H ─ C ─ C ─ C ─ C ─ C ─ H │ │ │ │ │ H CH3 H H H
Name the alcohol.
This is a tertiary alcohol: the carbon attached to the OH is also attached to three other carbons.

43. Alcohols
Draw the following alcohols.
2-hexanol
4-pentanol

44. Ethers
Oxygen is always in the middle between 2 carbon atoms or 2 hydrocarbon alkyl groups.
When naming ethers, name each side chain as an alkyl group and add ether at the end.

45. Ethers – Example #1 ethyl methyl ether or methyl ethyl ether H H H
│ │ │
H ─ C ─ O ─ C ─ C ─ H
ethyl methyl ether or
methyl ethyl ether

46. Ethers – Example #2 Name the ether. H H H H │ │ │ │
│ │ │ │
H ─ C ─ C ─ O ─ C ─ C ─ H
│ │ │ │
H H H H
Name the ether.

47. Aldehydes
functional group that has a single bond between C-H and a double bond between C=O
When naming aldehydes, drop the “e” of the alkane and add “al”.
Functional group always at the end
of the chain, no numbering required. O ||
– C – H

48. butanal Aldehydes - Example
H H H O │ │ │ ║ H ─ C ─ C ─ C ─ C ─ H │ │ │ H H H
butanal

49. Ketones
The functional group is in the middle and the carbon atoms are on both sides. Can never go at the end, otherwise it would be an aldehyde.
When naming ketones, drop the “e” of the alkane and add “one”.
Must use a number to indicate which carbon the double bonded oxygen is attached to - using the smallest possible number as before. O ║
R ─ C ─ R’

50. Ketones – Example #1 propanone
H O H
│ ║ │
H ─ C ─ C ─ C ─ H
│ │
H H
propanone
(needs no number, only one possible carbon the O can go on)

51. Name this ketone. Ketones – Example #2
H H O H H │ │ ║ │ │ H ─ C ─ C ─ C─ C ─ C ─ H │ │ │ │ H H H H
Name this ketone.

52. Organic Acids
The condensed formula will have – COOH at the end. (the functional group)
When naming organic acids, drop the “e” of the alkane and add “oic acid”.
Functional group always at the end of the chain, no numbering required.
Ethanoic Acid Butanoic Acid

53. Esters What comes from the organic acid O ║ R ─ C ─ O ─ R’
Esters are a result of combining an organic acid and an alcohol to produce an ester and water.
To name esters, name the chain on the right as an alkyl group (came from the alcohol). Name the chain on the left by dropping the “e” and add “oate” (what came from the organic acid).
What comes from
the alcohol

54. methyl came from methanol (alcohol) ethanoate came from ethanoic acid
Esters – Example #1
Organic Acid
Alcohol
methyl ethanoate:
methyl came from methanol (alcohol)
ethanoate came from ethanoic acid
(organic acid)

55. Esters – Example #2
Name the ester.
Name the organic acid and alcohol that the ester was produced from.

56. When naming amines, you drop the “e” of the alkane and add “amine”
functional group where the nitrogen is attached to a carbon or hydrogen.
When naming amines, you drop the “e” of the alkane and add “amine”

57. Amine – Example #2 │ │ │ │ .. H ─ C ─ C ─ C ─ C ─ N ─ H │ │ │ │ │
H H H H
│ │ │ │ ..
H ─ C ─ C ─ C ─ C ─ N ─ H
│ │ │ │ │
H H H H H
Name the amine.

58. Amides
When naming amides, drop the “e” of the alkane and add “amide”.

59. Amides - Example
butanamide

60. Organic Reactions Substitution Addition Combustion Fermentation
Reactions that involve organic compounds.
There are seven (7) reactions we will discuss:
Substitution
Addition
Combustion
Fermentation
Esterfication
Saponification
Polymerization

61. Addition Alkene or Alkyne + Halogen  Alkyl Halide
The double bond is broken, and the halogen adds at either side of where the double bond was.
One product
Two reactants

62. Alkane + Halogen  Alkyl Halide + Hydrogen Halide
Substitution
Alkane + Halogen  Alkyl Halide + Hydrogen Halide
The halogen atoms substitute for any of the hydrogen atoms in the alkane.
C2H6 + Cl2  C2H4Cl2 + H2

63. Combustion
Happens when an organic molecule reacts with oxygen gas to form carbon dioxide and water vapor. Also known as “burning”.

64. Fermentation
Process of making ethanol by having yeast digest simple sugars anaerobically. CO2 is a byproduct of this reaction.

65. Saponification
The process of making SOAP!!
Look for NaOH in the reactants!!

66. Esterification Organic Acid + Alcohol  Ester + Water
A dehydrating agent (H2SO4) removes H from the organic acid and removes the OH from the alcohol. The two molecules join where there H and OH were removed creating H2O.

67. Polymerization
Involves smaller molecules joining together to form one big molecule!
Two different types:
Addition and Condensation.
Addition: Breaking double/triple bonds to add on
Condensation: Dehydration Synthesis to add on

68. 1) Given the structural formula: The compound represented by this formula can be classified as an
A) ester
B) aldehyde
C) organic acid
D) ether
2) Given the balanced equation for an organic reaction: C2H2 + 2Cl2  C2H2Cl4
This reaction is best classified as
A) fermentation
B) addition
C) esterification
D) substitution

69. 3) Given the formulas of four organic compounds: Which pair below contains an alcohol and an acid?
A) b and d
B) a and b
C) a and c
D) c and d
4) The formula below represents a product formed when HCl reacts with CH3CH2CHCH2.
What is an IUPAC name for this product?

70. 5) Draw the structural formula for propanone.
6) Draw the structural formula for butanoic acid.

71. 7) Given the equation:
To which class of organic compounds does product X belong?