1. Welcome to the OC Organic Chem 1-119 in notes
OB: Mastering the alkanes, the alkenes, and the alkynes. Take out table P + Q now.
At the end of today you should be able to name and draw, and recognize any alkane, alkene, or alkyne, 1 → 10 carbons long.

2. All chemistry we have been doing is technically “inorganic” chem
All chemistry we have been doing is technically “inorganic” chem. The compounds are all found in nature. For a while, at the beginning, some molecules were considered “organic”, which meant that only living things (plants and animals) could produce them.
Urea was the first organic molecule that scientists synthesized, and they’ve been busy since. The organic molecules we will study are more complex than the simpler molecular and ionic compounds so far, but we get a bunch of tables to help us name them.
Some compounds, like acetic acid and ethanoic acid, are the SAME THING, but they have different naming styles. So what? Not to be scared of.
Organic chemistry is the real class in college that students cry in all of the time. It’s there exactly that their hopes and dreams for med school end. Not because it’s too hard, but because it’s too much to study and retain.
We will make it easy and it only lasts 2 weeks. You shouldn’t cry over this.

3. OUR FRIEND Carbon. 1. The first atom of organic chem.
Then comes hydrogen, H
Followed by some others, like oxygen, O
The halogens: F, Cl, Br, and I
And the other cool atoms: N and S
Count to 4, that’s most important Single, double and triple bonds.
Then count to 1, 2, 3, also important. But 4 is most important.
3. No metals, not ever in organic.
Table P, Q, and R. Take out P and Q now please.
OUR FRIEND

4. 4. You must use this table to learn to count carbon atoms in Latin.
Prefix
Number of carbon atoms
meth- 1
eth- 2
prop- 3
but- 4
pent- 5
hex- 6
hept- 7
oct- 8
non- 9
dec- 10
4. You must use this table to learn to count carbon atoms in Latin.
Memorize this, and remember it’s right there as table P, and look at it a lot.
All organic molecules use the number of carbons in their chemical names.
This is really important.

5. 5. Carbon makes 4 bonds because it has a 2-4 electron configuration, and it needs the octet for bonding stability.
All carbon atoms make 4 bonds. They can be:
4 single bonds,
2 single bonds + 1 double bond
2 double bonds
1 single + 1 triple bond
4 Bonds no matter what. Look at your hand, learn how many fingers FOUR is. Don’t forget how many 4 is, not ever.
Hydrogen has 1 electron and can only bond as a single bond.
Look at your hand, how many fingers is 1? Don’t forget that either.

6. 6. If you have 1 carbon atom, and enough hydrogen atoms, how many hydrogen atoms does it take to completely bond one carbon atom?
7. What’s the formula for this SIMPLEST of all organic molecules?

7. 6. If you have 1 carbon atom, and enough hydrogen atoms, how many hydrogen atoms does it take to completely bond one carbon atom? 4H + 1 C
7. What’s the formula for this SIMPLEST of all organic molecules? CH4 H
H C H
A ONE CARBON molecule is called
METHANE

8. 8. When 2 carbon atoms bond together (single bonds only now) how many atoms of Hydrogen can also bond together with them?
9. What is the name of a 2 carbon simple (single bond) hydrocarbon molecule? Look at table P and Q

9. 8. When 2 carbon atoms bond together (single bonds only now) how many atoms of Hydrogen can also bond together with them? C–C leaves room for 6 H atoms
9. What is the name of a 2 carbon simple (single bond) hydrocarbon molecule? Ethane Which can be written as __________

10. Structural Diagram and structural formula
Name all of the SINGLE BONDED CARBON hydrocarbons 1 to 10 carbons in length, draw the structural diagrams and structural formulas, for each.
# C
Name
Structural Diagram and structural formula 10 1 11 2 12 3 14 4

11. Structural Diagram and structural formula
Name
Structural Diagram and structural formula 15 5 16 6 17 7

12. Structural Diagram and structural formula
Name
Structural Diagram and structural formula 18 8 19 9 20 10

13. Vocabulary:
21. Organic chem: chemical compounds that at one time were thought to be made only by living organisms like plants or animals. This is not true, nor was it.
22. Carbon: the central atom in organic chem, it makes 4 bonds because of it’s electron configuration of It can make single or double or triple bonds to itself.
23. Hydrogen: the second atom of organic chem. It only makes single bonds, and is in abundance in organic molecules.
24. Oxygen: makes 2 bonds, double or two singles, and is in the midst of all the really cool organic molecules. Where it is changes chemical names and properties.
25. Nitrogen: makes 3 bonds, and has a simpler role in high school chem, but is very much the coolest atoms in amino acids and proteins
26. Halogens: make single bonds only. In our class makes decorations on compounds
27. Hydrocarbons: base molecles of organic chem, made up only of H + C (hence the name)

14. 28. ALKANES: hydrocarbons with only single C-C bonding
28. ALKANES: hydrocarbons with only single C-C bonding. Only contain carbon and hydrogen atoms. Chains of 1 to 10 labeled with prefixes in table P. All end in –ane.
29. AKLENES: hydrocarbons with only one double C=C bond. Only contain carbon and hydrogen atoms. Chains of 1 to 10 labeled with prefixes in table P. All end in –ene. In college molecules can have multiple double bonding, but we have a single double bond to keep it simple.
30. ALKYENES: hydrocarbons with only one triple C≡C bond. Only contain carbon and hydrogen atoms. Chains of 1 to 10 labeled with prefixes in table P. All end in –yne. In college molecules can have multiple triple bonding, but we have a single triple bond to keep it simple.

15. Look at Table Q. 31. What is the general formula for these ALKANES?
32. Alkane means that the hydrocarbon make ONLY SINGLE BONDS between the carbon atoms (methane is exceptional, only 1 carbon).
33. Hydrocarbons are the simplest organic molecules.
34. What are the only two atoms that are in hydrocarbons?
35. If it had an oxygen atom attached, or a chlorine atom attached, would it still be a hydrocarbon?
Will we learn about other kinds of molecules?
Homologous series means: _________________________

16. 38. The 2nd type of hydrocarbon chains are called alkenes.
39. Their general formula is
They’ve less hydrogens than alkanes because they have a double bond.
40. In our class they will contain JUST 1 double bond, but in the real world, more than one double bond is possible.
41, 42, and 43. We will draw the first three in a row now…
41. Is a JOKE. No “methene” is possible. You need at least 2 carbons to have a double bond between 2 carbon atoms! Now DRAW ethene and propene…

17. 43. Propene
Straight lines, or bent, the chain is 3 carbons in a row and that’s all that matters.
Double bond left or right, it’s the same thing, molecules float!
42. Ethene
Hydrogen atoms at an angle is cool, or you can stick with the 90° angles, it’s just a drawing.

18. 44. Try to draw butene now.

19. How do we tell these apart?
With 4 carbons things start to get a touch more complicated. You can you put that double bond in 2 different places (between carbon 1 + 2, or between carbon 2 + 3)
Where is that double bond? It’s attached to which carbon atoms?
How do we tell these apart?
It’s crooked, but still a line. Where is that double bond?

20. How do we tell these apart?
45. This is 1-butene, the double bond goes from the first carbon to the second carbon. (use smallest number possible)
How do we tell these apart?
46. This is 2butene, the double bond goes from the 2nd to the 3rd Carbon atom. (use the smallest numbers)

21. Draw these next 47
1-pentene 48
2-pentene 49
3-hexene

22. Draw these next 50
3-heptene 51
3-octene 52
4-nonene 53
Propene (no number, why??)

23. 1-pentene 2-pentene 3-hexene 3-heptene
Draw the following (you MAY omit the “H” atoms, but not the bonds
1-pentene
2-pentene
3-hexene
3-heptene

24. 3-octene -c-c-c=c-c-c-c-c-
Draw the following (you MAY omit the “H” atoms, but not the bonds
3-octene c-c-c=c-c-c-c-c-
4-nonene c-c-c-c=c-c-c-c-c-
1-decene

25. 54. The third group of hydrocarbons are the ALKYNES
Small change in name, this one has a triple bond. In our class the ALKYNES will ONLY have one triple bond.
55. Naming and drawing will be just like the alkynes, the number tells where the triple bond is placed
56. There is no “methyne” either, you need at least 2 carbons to triple bond together.

26. 57. Draw ethyne, and propyne now…

27. 57. Ethyne and one triple bonded carbon pair, and as many hydrogen atoms that fit, JUST 2.
This is NOT 1-propyne, because if the triple bond were on the right side, you’d just count carbons from that side (the end closest to the fancy part, here it’s a triple bond, is carbon #1.
Just PROPYNE

28. 59. Let’s draw 1-butyne and 2 butyne next (put your triple bond in the right place!)

29. Below is 2 butyne
The triple bond is between carbon #2 and #3, counting from EITHER direction.
That’s 1-butyne above, counting from the right side.
Right, left, who cares? Just keep track of the “first” carbon, it does not matter right or left.

30. Let’s draw some more…
decyne
pentyne
pentyne
hexyne

31. Let’s draw some more…
1-decyne
1-pentyne
2-pentyne
3-hexyne

32. Review: Use Table P to count to 10 in Latin prefixes
Use Table Q for hydrocarbons.
There are 3 kinds of hydrocarbons (3 homologous series) they contain ONLY Carbon + Hydrogen atoms
Alkanes all C-C bonds are single, these are “saturated” hydrocarbons - they hold the MOST hydrogen atoms
Alkenes Must contain only one C=C double bond in our class, The double bond must be enumerated unless too small to matter these are unsaturated hydrocarbons
Alkynes Must contain only one CΞC triple bond in our class, The triple bond must be enumerated unless too small to matter these are also unsaturated hydrocarbons

33. Organic Chem Class #3 They really like table ARRRRGGHHHHH!
OB: adding halogens into all three kinds of hydrocarbons.
Take out Table R
64. Why do Pirates Love Organic Chem?
They really like table ARRRRGGHHHHH!

34. Now let’s look at the top of Table R
The 1st “FUNCTIONAL GROUP” are halogens.
65. Functional groups are added to the hydrocarbons to make them fancier, to make them more difficult, to make them smell better or worse, to give them a wide variety of properties.
That’s the organic chem part.
The first, and the simplest functional groups we’ll add in are the halogens.

35. They all make only single bonds. Only single bonds. Only.
66. As you remember, group 17 contains the halogens: F, Cl, Br, and I
When they are added to hydrocarbons we need to BOND them to the chains, to the Carbon atoms.
67. Each halogen has 7 valence electrons. They all need to share ONE electron with a carbon atom, making a single bond.
They all make only single bonds. Only single bonds. Only.

36. 65. Halogens can be substituted into hydrocarbons that are saturated (alkanes)
66. Or they can be added into hydrocarbons that are unsaturated, like the alkenes Or added to the Alkynes).

37. 70. Ethane + Fluorine yields…
If we start with a simple ethane molecule we can substitute in a halogen for a hydrogen with a substitution reaction. We’re learning 2 new things at once.
68. Ethane is a saturated hydrocarbon molecule (alkanes have as many H atoms as possible).
69. We can’t ADD a halogen atom into ethane because it’s already SATURATED but we can substitute in an atom for an H atom This is a substitution reaction
70. Ethane + Fluorine yields…
+ F2
F HF
Fluoro-ethane + hydrogen monofluoride

38. Draw then name these molecules now.
71.
72. Br
F F F
73.
74. Cl F

39. Let’s name these molecules now.
71.
72. Br
F F
Bromo-ethane
1,2 di-fluoro-ethane F
73.
74. Cl F
Chloro-ethane
1,1 di-fluoro-ethane

40. 76. Draw and name this molecule
The rules to naming these halo-carbons is easy. We’ll write them once, practice them lots, then you will just remember them because they are easy…
75. Rules to naming halocarbons: 1. Figure out the base chain name, that’s going to be the “LAST NAME” of the molecule.
2. Any Double and Triple bonds will “trump” fancy functional groups They will decide the carbon atom counting.
3. If no double or triple bonds, figure out which side we’ll count the carbons from, the fancy atoms (or groups) will decide which is the “short end to count from”.
4. The halogens are named in ALPHABETICAL order first, numbers second.
H Br F F
76. Draw and name this molecule

41. But, Br is on the 3rd carbon.
There is a 4 carbon butane base chain that these halogens are attached to…
Bromine comes first, since Br is before F in the alphabet.
But, Br is on the 3rd carbon.
The F atoms are on the carbon atoms #
76. This would be 3-bromo 1,2-difluro-butane
H Br F F

42. 77. Name this molecule… Cl Cl Cl F Br F
First, how many carbons in a row, and are they single bonds only?
This is a nonane base chain. Which is carbon #1, then work out the first names

43. Cl Cl Cl F Br F 77. 2-bromo, 5,6,7-tri-chloro, 1, 4-difluro-nonane
Carbon #1 is the right side one, since the functional group closest to one end is closer to the right side carbon.
Names go alphabetical, and numbered, so…
bromo, 5,6,7-tri-chloro, 1, 4-difluro-nonane

44. I
I F Cl
78. Name this funky thing.
Base chain first always…

45. I I F Cl Name the base chain first 1-octyne
The base chain sets the carbon count.
The chlorine comes first, so…
chloro, 7-fluoro, 8,8-di-iodo, 1-octyne

46. Let’s substitute in a Cl, over + over + over 4x
Cl + HCl
Methane chlorine → chloromethane HCl
? #79
Cl + Cl2
chloromethane HCl

47. ? #80 Cl + HCl Cl + Cl2 Cl Cl + Cl2 Cl
79. Cl
+ Cl2
Cl + HCl Cl
Chloromethane chlorine makes dichloromethane HCl
? #80
Cl + Cl2 Cl

48. ? #81 Cl Cl + Cl2 Cl + HCl Cl Cl Cl Cl + Cl2 Cl
80. Do the next 2 substitution reactions, draw molecules, name the products Cl
Cl + Cl2
Cl + HCl Cl Cl
trichloromethane + HCl
? #81 Cl
Cl + Cl2 Cl

49. 81. Cl Cl
Cl + Cl2 Cl Cl Cl Cl
Trichloromethane + chlorine tetrachloromethane + HCl

50. Name us Cl F
Br – C – H
F – C – H Cl F

51. 82 + 83. Name us Cl F Br – C – H F – C – H Cl F Bromodichloromethane
Trifluoromethane

52. Name us Cl
Br – C – H Cl
Trichlorofluoromethane

53. 84. Addition reactions… Ethene + Bromine → (unsaturated hydrocarbon + halogen…)

54. 85. Addition reactions… Ethyne + chlorine → (unsaturated hydrocarbon + halogen…)

55. 86. Addition reactions… 1pentyne + fluorine → (unsaturated hydrocarbon + halogen…)

56. propane, pentane, 2-butene, and then 3-hexyne
87. Draw structural diagrams for these molecules (omit your H’s if you want to)
propane, pentane, 2-butene, and then 3-hexyne

57. 87.
propane pentane butene 3-hexyne

58. Draw these:
3-bromo, 4,5-dichloro, 1-heptene
5,5,5-trifluoro, 1-pentyne

59. -CΞC-C-C-C- -C=C-C-C-C-C-C- Cl F F F
bromo,5,6 dichloro, 1-heptene
,5,5-trifluoro, 1-pentyne
Br Cl
-C=C-C-C-C-C-C- Cl F
-CΞC-C-C-C- F F

60. 90. Name Me
H H Cl F H H C C C C C H
F H H H H
Which is carbon #1???

61. First carbon on left (F) attached, so
90. Name Me
H H Cl F H H C C C C C H
F H H H H
First carbon on left (F) attached, so
3-chloro, 1,4-difluoro-pentane

62. Alcohols, ethers, aldehydes, & ketones
Organic Classes # 4
The next 4 functional groups of Table R
Alcohols, ethers, aldehydes, & ketones

63. Today we will look into the alcohols, the ethers, the aldehydes + the ketones (not key-tones)
91. According to table R, alcohols have an “–OH” group which is NOT a hydroxide. When the anion hydroxide is ionically bonded to a metal, that is an Arrhenius base. This is MOLECULAR.
92. When the –OH group is bonded (covalently) to a hydrocarbon, it’s an alcohol.

64. 93. The general formula for alcohols is R ― OH
Where R is any hydrocarbon that the ―OH group can bond onto.
94. Draw the ONE Carbon Alcohol now

65. CH3OH Draw and name each alcohol molecule methanol
94. one carbon alcohol
methanol
The CONDENSED STRUCTRUAL FORMULA IS WRITTEN THIS WAY:
CH3OH
The –OH really means
–O–H
But we abbreviate it and just “know” that the oxygen and hydrogen make a single covalent bond.
It’s prettier that way.

66. 95. Draw the two carbon alcohol
96. Draw the TWO DIFFERENT three carbon alcohols

67. 95. Ethanol
96A B.
1-propanol propanol

68. 97. Draw & name each 5 carbon alcohol molecule possible

69. 1-pentanol 2-pentanol 3-pentanol
97. Draw and name each 5 carbon alcohol molecule that you can…
H H H H H
Name the base chain (count carbon atoms)
Enumerate where the alcohol group is located.
Alcohol names always end with an -anol
suffix
1-pentanol H C C C C C OH
H H H H H
H H H H H
2-pentanol H C C C C C H
H H H OH H
H H H H H
3-pentanol H C C C C C H
H H OH H H

70. This is a list of ALL the alcohols in our class, none are missing.
# names of the
carbons alcohols
methanol
ethanol
propanol, 2-propanol
butanol, 2-butanol
pentanol, 2-pentanol, 3-pentanol
hexanol, 2-hexanol, 3-hexanol
heptanol, 2-heptanol, 3-heptanol, 4-heptanol
octanol, 2-octanol, 3-octanol, 4-octanol
nonanol, 2-nonanol, 3-nonanol, 4-nonanol, 5-nonanol
decanol, 2-decanol, 3-decanol, 4-decanol, 5-decanol

71. Ethers Ethers are easy because they have a single atom of oxygen in the middle, and two different “R” groups, left + right.
98. Ethers have a functional group that looks like this:
Which means an R group attached to an oxygen atom, which is attached to ANOTHER R group on the other side.

72. Ethers We need to introduce one more new thing now.
Methane is CH4
Ethane is CH3CH3
Propane is CH3CH2CH3
There is NO WAY to attach a methane to an oxygen atom and no way to attach an ethane, or propane, etc.
But if we remove a hydrogen atom, we can attach what’s left of it to the oxygen atoms.

73. Ethers are R―O―R’ which means that on either side of the ether there is a hydrocarbon chain, one to ten carbons long.
But not the “whole” methane, or ethane, propane, butane, pentane, hexane, etc.
99. Methane minus 1 hydrogen is called methyl Ethane minus 1 hydrogen atom is called ethyl
101. Propane minus 1 hydrogen atom is called propyl
102. Butane minus 1 hydrogen atom is called butyl.
103. Then comes pentyl, hexyl, heptyl, octyl, nonyl, and decyl.

74. 104. Draw the simplest ether, with a one carbon on each side.
105. Draw the next simple ether, with a single carbon on one side, and 2 carbons on the other side.

75. 104. Methyl methyl ether sounds too funny. It’s wrong.
This is dimethyl ether. Condensed structural formula is CH3OCH3
H H O H C C H
H H
105. Methyl ethyl ether is sort of wrong.
This is ethyl methyl ether (alphabetical order) Condensed structural formula is CH3CH2OCH3
H H H O H C C C H
H H H

76. Draw these ethers.
106. Butyl ethyl ether
107. Methyl pentyl ether
108. Heptyl hexyl ether

77. Draw these ethers… 106. Butyl ethyl ether 107. Pentyl methyl ether
108. Heptyl hexyl ether
H H H H H H H C C C C O C C H
H H H H H H
H H H H H H H C C C C C O C H
H H H H H H
H H H
H H H H H H H H H H H C C C C C C C O C C C C C C H
H H H
H H H H H H H H H H

78. 109. Aldehydes and Ketones we will examine together, since they are nearly the same thing, but they are PHYSICALLY DIFFERENT, they are ISOMERS.
110. They both have a C=O bond, just in different places.
111. Aldehydes always have the C=O at the end of a hydrocarbon chain,
112. Ketones always have the C=O in the middle of a chain.

79. 113. Draw and name the 3 carbon aldehyde 114
113. Draw and name the 3 carbon aldehyde Draw and name the 3 carbon ketone now

80. CH3CH2CHO CH3COCH3 116. 3 carbon aldehyde propanal
carbon ketone propanone
CH3COCH3

81. The smallest ketone is propanone.
115. Draw METHANAL
116. Draw ETHANAL
117. Draw BUTANAL
118. Draw BUTANONE
119. Draw 2-Pentanone
The smallest ketone is propanone.
There must be at least 3 carbons for this C=O bond to “be in the middle” of a chain of carbons.

82. 115. METHANAL 116. ETHANAL 118. Butanone
117. BUTANAL Pentanone H C C H O H H C H
H H O H H C C C C H
H H H
H H H O H C C C C H
H H H O H
H H H H C C C C C H
H H H H