Welcome to the OCOrganic Chem

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.

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.

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.

2. 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

PrefixNumber 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. 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 bond2 double bonds1 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. If you have 1 hydrogen 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?

6. If you have 1 hydrogen 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

H

A ONE CARBON molecule is called

METHANE

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

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

Name all of the SINGLE BONDED CARBON hydrocarbons 1 to 10 carbons in length, draw the structural diagrams for each.

# C Name Structural Diagram

10 1

11 2

12 3

14 4

# C Name Structural Diagram

15 5

16 6

17 7

# C Name Structural Diagram

18 8

19 9

20 10

Vocab Alert:

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 2-4. 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)

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.

Look at Table Q.

31. What is the general formula for these ALKANES?

32. Alkane means that the hydrocarbon has NO double bonded carbon atoms, and no triple bonded carbon atoms. ONLY SINGLE BONDS (or none for methane).

33. Hydrocarbons are the simplest organic molecules.

34. What are the only two atoms that are in hydrocarbons?

35. If it had an oxgyen atom attached, or a chlorine atom attached, would it still be a hydrocarbon?

36.Will we learn about other kinds of molecules?

37.Homologous series means: _________________________

38. The 2nd type of hydrocarbon chains are called alkenes.

39. Their general formula is They have less hydrogens than the alkanes because they contain 1 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…

Try that “methene” but don’t get frustrated, it’s not possible. You need at least 2 carbons to have a double bond between 2 carbon atoms!

Now go for ethene and propene…

42. Ethene

Hydrogen atoms at an angle is cool, or you can stick with the 90° angles, it’s just a drawing.

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!

44. Try to draw butene now.

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?

It’s crooked, but still a line. Where is that double bond?

How do we tell these apart?

45. The carbon atoms need to be named 1, 2, 3, and 4. The “rule” is that the carbon atom closest to the double bond is #1. So, the first molecule has carbon #1 on the left. The double bond is between carbon #1 and #2, so we’ll call it 1-butene.

46. This one at right has the double bond between the 2nd and 3rd carbon. Note that from EITHER SIDE that is true. You could call the left carbon #1, or the far right hand carbon #1, but the double bond still attaches carbon #2 to carbon #3

This one is 2-butene.

Draw these next

47 1-pentene

48 2-pentene

49 3-hexene

Draw these next

50 3-heptene

51 3-octene

52 4-nonene

53 1-decene

Draw the following (you MAY omit the “H” atoms, but not the bonds

1-pentene

2-pentene

3-hexene

3-heptene

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

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 bond placement must be stated (unless it’s the same from both ends).

56. There is no “methyne” either, you need at least 2 carbons to triple bond together.

57. Draw ethyne, and propyne now…

57. Ethyne and one triple bonded carbon pair, and as many hydrogen atoms that fit, JUST 2.

58. 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

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

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.

Below is 2 butyne

The triple bond is between

carbon #2 and #3, counting from EITHER

direction.

Let’s draw some more…

60. 1-decyne

61. 1-pentyne

62. 2-pentyne

63. 3-hexyne

Let’s draw some more…

1-decyne

1-pentyne

2-pentyne

3-hexyne

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 matterthese are unsaturated hydrocarbons

Alkynes Must contain only one CΞC triple bond in our class, The triple bond must be enumerated unless too small to matterthese are also unsaturated hydrocarbons

Organic Chem Class #3OB: adding halogens into all three kinds of hydrocarbons.

Take out Table R

64. Why do Pirates Love Organic Chem?

They really like table ARRRRGGHHHHH!

Now let’s look at the top of Table R

The first “FUNCTIONAL GROUP” are the halogens.

65. Functional groups are added to 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.

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.

67. Each halogen has 7 valence electrons. They all need to share ONE electron with something else (a carbon atom) to make a single bond.

They all make only single bonds. Only single bonds. Only.

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, 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

Draw and name these molecules now.

Br

Cl

F F

F

F

71. 72.

73. 74.

Let’s name these molecules now.

Br

Cl

F F

F

F

Bromo-ethane

Chloro-ethane

1,2 di-fluoro-ethane

1,1 di-fluoro-ethane

71. 72.

73. 74.

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. Double and Triple bonds “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.

Cl Br F F76. Draw and name this molecule

There is a 4 carbon butane base chain that these halogens are attached to…

Bromine comes first, since B is before Cl or F.

Br is on the 2nd carbon.

Cl is second, it’s on the first carbon.

Both of the F atoms are on the carbon atoms # 3 + 4

76. This would be 2-bromo, 1-chloro, 3,4-difluro-butane

Cl Br F F

Cl Cl Cl F

Br F

77. Name this molecule…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

Cl Cl Cl F

Br FCarbon #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…

77. 2-bromo, 5,6,7-tri-chloro, 1, 4-difluro-nonane

I F Cl

I

78. Name this funky thing.

Base chain first always…

I F Cl

I

Name the base chain first 1-octyneThe base chain sets the carbon count.The chlorine comes first, so…

78. 6-chloro, 7-fluoro, 8,8-di-iodo, 1-octyne

+ Cl2

Let’s substitute in a Cl, over + over + over 4x

Cl + HCl

Methane + chlorine → chloromethane + HCl

Cl + Cl2

chloromethane + HCl

? #79

Cl + Cl2 Cl + HCl

ClChloromethane + chlorine makes dichloromethane + HCl

79.

Cl + Cl2

Cl ? #80

80. Do the next 2 substitution reactions, draw molecules, name the products

Cl + Cl2

Cl

Cl

Cl + HCl

Cltrichloromethane + HCl

Cl

Cl + Cl2

Cl ? #81

Cl

Cl

ClCl

Cl

Cl + Cl2

ClTrichloromethane + chlorine tetrachloromethane + HCl

81.

82 + 83. Name us

82 + 83. Name us

Trichloro, fluoro-methane

Tribromo, fluoro-methane

Organic Class #3bYou’ll get up, look at the models I made, draw the

structural diagrams, and name them, if you get them all correct I will give you…

Not really, you have to learn to work for yourself, not for pay. It’s not about cash, it’s about your mind.

Hard work now pays off later.

84, 85, 86, 87.Draw structural diagrams for these molecules (omit your H’s if you want to)

propane, pentane, 2-butene, and then 3-hexyne

84, 85, 86, 87.propane

pentane

2-butene

3-hexyne

88 + 89. Draw these:

3-bromo, 4,5-dichloro, 1-heptene

5,5,5-trifluoro, 1-pentyne

88. 3-bromo, 4,5-dichloro, 1-heptene

89. 5,5,5-trifluoro, 1-pentyne

-C=C-C-C-C-C-C- Br Cl

Cl

-CΞC-C-C-C-

F

FF

C C C C

H H Cl F H

HH

F H H H H

90. Name Me

C

Which is carbon #1???

C C C C

H H Cl F H

HH

F H H H H

90. Name Me

C

First carbon on left (F) attached, so

3-chloro, 1,4-difluoro-pentane

Get up, bring paper and your reference tables to guide you through these molecules…

Organic Classes # 4

The next 4 functional groups of Table R

Alcohols, ethers, aldehydes, & ketones

On table R we’ll notice that there is something called an “R” group.

91. “R” can stand for any hydrocarbon, of any length. It could even stand in for just an “H” atom. It’s generic.

92. For halocarbons, the general formula is R ― X

Where R stands for any hydrocarbon, say a methane, or an ethane, or a propane.

X stands for any halogen.

93. Chloro-hydrocarbon could be R ― Cl

Today we will look into the alcohols, the ethers, the aldehydes + the ketones (not key tones)

By the time we finish today you should be able to recognize what type of molecule you are looking at by its structural diagram, or condensed structural formula. You will be able to draw one from its name or formula as well. This will keep you busy.

Alcohols94. 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 different.

95. When the –OH group is bonded covalently to a hydrocarbon, it’s called an alcohol.

94. The general formula for alcohols is R ― OH

95. Where R is any hydrocarbon that the ―OH group can bond onto.

Draw and name each alcohol molecule

96. one carbon

97. two carbons

98. three carbons

H

H

H OH methanol

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.

C

Draw and name each alcohol molecule

96.

97.

98A. 98B.

H

H

H OH methanol

H H

H H

H OH ethanol

H H H

H H H

H OH

1-propanol 2-propanol

H OH H

H H H

H H

C

CC

C C C C C C

99. Draw & name each 5 carbon alcohol molecule possible

99. Draw and name each 5 carbon alcohol molecule that you can…

H H H H H

H H H H H

H H H H H

H

H

H

H H H H H

H H H OH H

H

OH

H

H H OH H H

1-pentanol

2-pentanol

3-pentanol

Name the base chain

(count carbon atoms)

Enumerate where the

alcohol group is located.

Alcohol names

always end with an-anolsuffix

C C C C C

C C C C C

C C C C C

This is a list of ALL the alcohols in our class, none are missing. # names of thecarbons alcohols 1 methanol 2 ethanol 3 1-propanol, 2-propanol

4 1-butanol, 2-butanol 5 1-pentanol, 2-pentanol, 3-pentanol 6 1-hexanol, 2-hexanol, 3-hexanol

7 1-heptanol, 2-heptanol, 3-heptanol, 4-heptanol 8 1-octanol, 2-octanol, 3-octanol, 4-octanol

9 1-nonanol, 2-nonanol, 3-nonanol, 4-nonanol, 5-nonanol 10 1-decanol, 2-decanol, 3-decanol, 4-decanol, 5-decanol

Ethers 101. Ethers have a general formula of ___________

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, or an ethane, or propane, etc.

But if we remove a hydrogen, we can attach what’s left of methane, or ethane, or propane.

100. Ethers are easy because they have a single atom of oxygen in the middle, and two different “R” groups, left + right.

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.

102. Methane minus 1 hydrogen is called methyl103. Ethane minus 1 hydrogen atom is called ethyl

104. Propane minus 1 hydrogen atom is called propyl105. Butane minus 1 hydrogen atom is called butyl.

106. Then comes pentyl, hexyl, heptyl, octyl, nonyl, + decyl.

107. Name this: CH3―O―CH3

108. Name this one: CH3CH2―O―CH3

O CC

H H

H H

HH

O CC

H H H

HH C

H H H

CH3―O―CH3 is methyl methyl ether but we say dimethyl ether

CH3CH2―O―CH3 is ethyl methyl ether

109. Even though it doesn’t really matter because it’s just left and right, we alphabetize the alkyl groups. We will only add alkane chains to ethers, no double or triple bonds. KISS.

Draw these ethers.

110. Butyl ethyl ether

111. Methyl pentyl ether

112. Heptyl hexyl ether

Draw these ethers. (wow!)

Butyl ethyl ether CH3CH2CH2CH2OCH2CH3

Methyl pentyl ether CH3OCH2CH2CH2CH2CH3

Heptyl hexyl ether CH3CH2CH2CH2CH2CH2CH2OCH2CH2CH2CH2CH2CH3

Draw these ethers…

Butyl ethyl ether

Pentyl methyl ether

Heptyl hexyl ether

O

H H H H H H

H H H H H H

HH

O

H H H H H H

H H H H H H

HH

O

H H H H H H H H H H

H H H H H H H H H H

HH

H H H

H H H

C C C C C C

C C C C CC

C C C C C C C C C C C C C

Ethers always have at least 1 carbon on each side – the smallest ether is dimethyl ether.

They are named alphabetically. They always have the last name ether.

There is a mistake in your reference table, it shows “methyl ethyl” ether when really what’s showing is ethyl methyl ether.

Really that’s the same only named backwards.

114. Aldehydes and Ketones we will examine together, since they are nearly the same thing, but they are located in different places.

115. They both have a C=O bond, just in different places.

116. Aldehydes always have the C=O at the end of a hydrocarbon chain,

117. Ketones always have the C=O in the middle of a chain.

118. Draw and name the 3 carbon aldehyde

119. Draw and name the 3 carbon ketone now

118. 3 carbon aldehyde propanal

119. 3 carbon ketone propanone

H H O

H H

HH C C C

H O H

H H

HH C CC

CH3CH2CHO

CH3COCH3

120. Draw METHANAL (no such thing as methanone)

121. Draw ETHANAL (no such thing as ethanone)

122. Draw BUTANAL

123. Draw 2-Pentanone

Need at least 3 carbons to “be in the middle” of a chain of

carbons. Ketones “start” at 3 or

propanone.

120. METHANAL 121. ETHANAL

122. BUTANAL 123. 2-Pentanone

HH

O

CHH

O

C

H

H

H H H O

H H H

H H

H H H O H

H H H H

H H

It’s the placement of that double bonded oxygen that makes these 2 molecules different.

C

C C C CC C C CC