Download Organic Chem Slideshow Part 1

Welcome to the OC
Organic 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
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. 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. 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
A ONE CARBON molecule is called
H
METHANE
C
H
H
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
10
1
11
2
12
3
14
4
Name
Structural Diagram
#C
15
5
16
6
17
7
Name
Structural Diagram
#C
18
8
19
9
20
10
Name
Structural Diagram
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?
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
4-nonene
1-decene
-c-c-c=c-c-c-c-c-c-c-c-c=c-c-c-c-c-
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!)
Below is 2
butyne
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.
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 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
Organic Chem Class #3
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!
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.
71.
72.
Br
F F
73.
74.
F
Cl
F
Let’s name these molecules now.
71.
72.
Br
Bromo-ethane
73.
F F
1,2 di-fluoro-ethane
74.
F
Cl
F
Chloro-ethane
1,1 di-fluoro-ethane
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.
76. Draw and name this
molecule
Cl
Br
F
F
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 F
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…
77.
2-bromo, 5,6,7-tri-chloro, 1, 4-difluro-nonane
I
I
F Cl
78. Name this
funky thing.
Base chain first always…
I
I F Cl
Name the base chain first 1-octyne
The base chain sets the carbon count.
The chlorine comes first, so…
78.
6-chloro, 7-fluoro, 8,8-di-iodo, 1-octyne
Let’s substitute in a Cl, over + over + over 4x
+ Cl2
Methane
+
chlorine
Cl + Cl2
chloromethane
+ HCl
Cl + HCl
→
chloromethane
?
+ HCl
#79
79.
Cl + HCl
Cl + Cl2
Cl
Chloromethane + chlorine
Cl + Cl2
Cl
makes
dichloromethane +
?
HCl
#80
80. Do the next 2 substitution reactions,
draw molecules, name the products
Cl
Cl + Cl2
Cl
Cl + HCl
Cl
trichloromethane + HCl
Cl
Cl + Cl2
Cl
?
#81
81.
Cl
Cl
Cl + Cl2
Cl
Trichloromethane + chlorine
Cl
Cl
Cl
tetrachloromethane + HCl
82 + 83. Name us
82 + 83. Name us
Trichloro,
fluoromethane
Tribromo,
fluoromethane
Organic Class #3b
You’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
Br Cl
-C=C-C-C-C-C-CCl
F
-CΞC-C-C-C- F
F
89. 5,5,5-trifluoro, 1-pentyne
90. Name Me
H
H
H
Cl
F
H
C
C
C
C
C
F
H
H
H
H
Which is carbon #1???
H
90. Name Me
H
H
H
Cl
F
H
C
C
C
C
C
F
H
H
H
H
H
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.
Alcohols
94. 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
H
H
C
OH
methanol
H
97. two carbons
The –OH really means
–O–H
98. three carbons
But we abbreviate it and
just “know” that the oxygen
and hydrogen make a single
covalent bond.
It’s prettier that way.
Draw and name each alcohol molecule
96.
H
H
C
OH
methanol
H
97.
98A.
H
H
H
H
C
C
H
H
OH
H
H
H
C
C
C
H
H
H
1-propanol
OH
ethanol
98B.
H
H
H
H
C
C
C
H
OH H
2-propanol
H
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
C
C
C
C
C
H
H
H
H
H
H
H
H
H
H
C
C
C
C
C
H
H
H
OH H
H
H
H
H
H
C
C
C
C
C
H
H
OH
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
-anol
suffix
This is a list of ALL the alcohols in our class, none are missing.
#
carbons
1
2
3
names of the
alcohols
methanol
ethanol
1-propanol, 2-propanol
4
5
6
1-butanol, 2-butanol
1-pentanol, 2-pentanol, 3-pentanol
1-hexanol, 2-hexanol, 3-hexanol
7
8
1-heptanol, 2-heptanol, 3-heptanol, 4-heptanol
1-octanol, 2-octanol, 3-octanol, 4-octanol
9
10
1-nonanol, 2-nonanol, 3-nonanol, 4-nonanol, 5-nonanol
1-decanol, 2-decanol, 3-decanol, 4-decanol, 5-decanol
100. Ethers are easy because they have a single
atom of oxygen in the middle, and
two different “R” groups, left + right.
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.
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 methyl
103. Ethane minus 1 hydrogen atom is called ethyl
104. Propane minus 1 hydrogen atom is called propyl
105. 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:
H
H
C
H
CH3CH2―O―CH3
H
O
C
H
H
H
H
H
C
C
H
H
H
O
C
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
H
H H
H H
C
C
C
H H
Pentyl methyl ether
H
C
O
H H
H H
H
H H
C
C
C
C
H H
H
C
H H
H
H
C
C
H
H
H
H
C
O
H
H
Heptyl hexyl ether
H
H
H
H
H
H
H
H
C
C
C
C
C
C
C
H
H
H
H
H
H
H
O
H
H
H
H
H
H
C
C
C
C
C
C
H
H
H
H
H
H
H
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
H
H
H
O
C
C
C
H
H
H
CH3CH2CHO
119. 3 carbon ketone propanone
H
H
O
H
C
C
C
H
H
H
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
O
H
C
H
H
O
H
C
C
H
H
122. BUTANAL
H
H
H
123.
H
C
C
C
H
H
H
O
C
H
H
2-Pentanone
H
H
H
C
C
C
H
H
H
O
H
C
C
H
It’s the placement of that double bonded oxygen that
makes these 2 molecules different.
H