1. Reference Table: P, Q, and R
PACKET #13:
Organic Chemistry
Reference Table: P, Q, and R

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

3. 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

4. Carbon Bonding
Carbon can forms bonds with other elements or with other carbons; carbon can form chains of carbon of unlimited length
chains can be straight
chains can be branched
chains can be closed to form rings
chains can form networks 

5. Characteristics of Organic Compounds
1. Generally non-polar (generally insoluble in water)
2. Soluble in non-polar solvents
(likes dissolve in likes )
3. Non-electrolytes
4. Have low melting points due to weak intermolecular forces
5. Reactions generally occur slowly
6. Reactions have high activation energy, and therefore lower reactions

6. Hydrocarbons
Definition - compounds composed of only hydrogen and carbon
Homologous series - group of organic compounds with similar properties and related structures (differ from each other by CH2)

7. Alkanes Hydrocarbons with the formula CnH2n+2 (Table Q)
All alkanes end in “ANE”.
Example: methane, ethane, propane
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. Alkanes
All the structural formulas to the right are considered saturated because the carbons are connected only by single bonds.

10. 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 hydrogen's so each carbon satisfies the 4 bond rule!
Always check your molecular formula with your structural formula.

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

12. 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

13. Naming Branches (Side Chains)
Branches are also called side chains.
After naming the longest chain,
draw a line through all the carbons you use.
Everything that is left are the side chains.
Do not count or name any carbon twice If you use the carbon in the longest chain name, you can’t use it in a side chain.
You must use the Alkyl Group and ending “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 the side chain is on the #3 carbon of pentane
The last step before we can name these is to determine which carbon of the longest chain is the side chain on (using the smallest number), and put that number with a dash in front of the side chain name.
STEP 1:
Numbering from the side that puts you on the lowest number:
the side chain is on the #3 carbon of pentane

16. Be Careful. Side-chains CANNOT go on the end
Be Careful!! Side-chains CANNOT go on the end!!! Bend your arm … it’s still your arm!!

17. STEP 2
3 - methyl pentane

18. Use the same rules when dealing with multiple side chains.
Example:

20. Example: Draw each isomer
Hexane (C6H14)
2-methylpentane (C6H14)

21. Draw three (3) isomers of nonane.

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

23. Naming Alkenes
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.

24. Writing the condensed formula for 3-hexene
Naming Alkenes
Writing the condensed formula for 3-hexene

25. Draw the structural formula and condensed formula for 2- pentene.

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

27. 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.

28. Naming Alkynes
Writing the condensed formula for 2-hexyne

29. Benzene Series Carbon structures that form a ring
Have the general formula CnH2n-6
6 carbon atoms in a ring

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

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

32. Halides – Example #1
2-bromopropane

33. 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.

34. Halides – Example #3
Name this halide.

35. 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.

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

37. Alcohols
one or more hydrogen atoms of a hydrocarbon are replaced by an -OH group (hydroxyl group).
When naming alcohols, drop the “e” and add “ol”.
2 hydroxyl groups use “diol”
3 hydroxyl groups use “triol”

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

39. Alcohols – Example #1 H H H │ │ │ H ─ C ─ C ─ C ─ OH │ │ │ H H H
Name the alcohol.

40. Alcohols – Example #2 H H OH │ │ │ H ─ C ─ C ─ C ─ OH │ │ │ H H H
Name the alcohol.

41. Alcohols – Example #3 H H OH │ │ │ H ─ C ─ C ─ C ─ OH │ │ │ H OH H
Name the alcohol.

42. Alcohols – Example #4
H OH H H H │ │ │ │ │ H ─ C ─ C ─ C ─ C ─ C ─ H │ │ │ │ │ H H H H H
Name the alcohol.

43. Alcohols Draw the following alcohols. 2,2,3-octantriol 2-hexanol
2,4-pentandiol

44. Aldehydes
functional group that has a single bond between C-H and a double bond between C=O (CHO – condensed)
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

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

46. Organic Acids
Functional group with a terminal (end) C-OH and that same C has a double bond to O.
The condensed formula will have –COOH at the end.
Organic acids are weak acids (ex – vinegar)
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

47. 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’

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

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

50. 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.

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

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

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. Esters – Example #1 methyl ethanoate:
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. Amines
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. Amines – Example #1 H H Notice that Nitrogen │ │ .. only needs to make
H─C─C─N─H 3 bonds and it has
│ │ │ an extra pair of electrons.
H H H
ethanamine

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

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

60. Amides - Example
butanamide

61. Amino Acids
NOT ON TABLE R. A combination of an amine (NH2) and an organic acid (COOH).
Amine and acid groups are on opposite ends of the molecule.
The general formula is

62. 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:
Highest BP/MP Lowest BP/MP
*Alcohols Ethers Hydrocarbons
*Acids Amines
Aldehydes
Ketones

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

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

65. Substitution
Alkane + Halogen  Alkyl Halide + Hydrogen Halide
The halogen atoms substitute for any of the hydrogen atoms in the alkane. This happens one atom at a time. The halide generally replaces an H on the end of the molecule.
C2H6 + Cl2  C2H5Cl + HCl
The second Cl can then substitute for another H:
C2H5Cl + HCl  C2H4Cl2 + H2

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

67. Fermentation
Process of making ethanol by having yeast digest simple sugars anaerobically. CO2 is a byproduct of this reaction.
The ethanol produced is toxic and it kills the yeast when the percent by volume of ethanol gets to 14%.

68. 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.

69. Saponification The process of making SOAP!!
Basically the opposite reaction of esterficaton: Ester  Acid + Alcohol

70. Polymerization
Involves smaller molecules joining together to form one big molecule!
Two different types:
Addition and Condensation.
Examples: PVC pipes, teflon, vinyl siding, polyester, nylon.

88. Review Questions
2) Which structural formula represents a molecule that is not an isomer of pentane?
1) Which pair of compounds are isomers?
A) P2O5 & P4O10
B) CH3OCH3 & C2H5OH
C) NO2 & N2O4
D) HCOOH & CH3COOH

89. 3) Which compound is a saturated hydrocarbon?
A) hexanol
B) hexane
C) hexanal
D) hexene
4) Which formula represents an unsaturated hydrocarbon?
A) C5H14
B) C5H8
C) C3H8
D) C2H6
5) Which formula represents a hydrocarbon?
A) CH3CH2CH2CH3
B) CH3CH2COOCH3
C) CH3CH2CH2COOH
D) CH3CH2CH2CHO

90. 6) What is the IUPAC name of the compound having the following structural formula?
A) 2-pentyne
B) 3-pentene
C) 2-pentene
D) 3-pentyne
7) Which structural formula correctly represents a hydrocarbon molecule?

91. 8) What is the total number of electron pairs that are shared between the two carbon atoms in a molecule of ethyne?
1 B) 2 C) 3 D) 4
9) Given the equation:
X + Cl2  C2H5Cl + HCl
Which molecule is represented by X?
A) C3H8
B) C2H4
C) C2H6
D) C3H6
10) Which structural formula represents 2-pentyne?

92. 11) Given the structural formula: The compound represented by this formula can be classified as an
A) ester
B) aldehyde
C) organic acid
D) ether
12) 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

93. 13) 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
14) The formula below represents a product formed when HCl reacts with CH3CH2CHCH2.
What is an IUPAC name for this product?

94. 15) Given the structural formula of pentane:
Draw a structural formula for an isomer of pentane.
16) Draw the structural formula for propanone.
17) Draw the structural formula for butanoic acid.

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