Organic Chem
Class # 5
Acids, esters, amine and amides
Made easy and palatable by yours
truly. Peace Love + Organic Chem
91. An organic acid will release H+1 ions, but has a different formula look than our
“regular” acids. The only acid in table K that is organic is ethanoic.
Ethanoic acid has a different sort of formula as well.
92. All organic acids have a “—COOH” group. It’s that last H that will ionize away.
O
O
R—C
OH
93. We’ll draw it this
way most of the time.
R
C—OH
94. Computers make
this easier to type.
Both ways are ok.
Draw
95. Methanonic Acid
96. Ethanonic Acid
97. Propanoic Acid
98. Hexanoic Acid
Draw
O
95. Methanonic Acid
H O
H—C—OH
H—C—C—OH
96. Ethanonic Acid
H H O
97. Propanoic Acid
H
H—C—C—C—OH
H H
98. Hexanoic Acid
H
H
H
H
H
H
O
C
C
C
C
C
C
H
H
H
H
H
H
99. When you combine an organic
acid with an alcohol you will end
up with an ester and water.
100. This reaction is called
ESTERFICATION
101. One of the best
smells ever
is the ester in bananas!
102. The functional group for esters is:
O
R —C—O—R’
103. On one side
there’s an R group.
On the other side
there’s a different
one called R‘
(that’s R prime)
104. Unlike a lot of molecules, such as the ethers, or even most of
the halocarbons, these molecules are not just left and right. There
are 2 parts. To help you remember (me too) I call one side the
“oxygen tail”. That’s the part that gets named first.
Let’s look at the reference table at methyl propanoate. (the methyl = 1, the prop = 3)
105. Draw Methyl Propanoate
O
CH3CH2–C–O–CH3
The “propanoate” is on
this side, it counts the 3
carbons on the left.
The “methyl” is on
this side, AFTER
the oxygen atom.
To draw an ester, start with the functional group
and work out from there.
106. Draw butyl pentanoate.
O
―C―O―
The “other” side gets the last
part of the name (penta), and it
INLCUDES that carbon in the
functional group.
The “oxygen tail” side get the first
part of the name (butyl).
Do the oxygen tail side first, the butyl side
106. Draw butyl pentanoate.
O
―C―C―C―C―C―O―C―C―C―C―
We will ALWAYS name the “R” group on the oxygen tail FIRST. The R groups
will be
Methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonly, or decyl.
There are no other choices.
On the “other” side of the ester, we’ll start with table P names, but they end
in –anoate, like:
Methanoate, ethanoate, propanoate… or octanoate, nonanoate, or decanoate.
107. Draw these now…
Methyl hexanoate
Ethyl methanoate
Methyl
Hexanoate
107.
Ethyl
methanoate
108. Now draw Ethyl propanoate and
Propyl ethanoate
Propyl
ethanoate
108.
Ethyl
propanoate
109. Draw one more, get it right the
first time. No mistakes…
Propyl propanoate
109. Propyl
propanoate
Amines and Amides are similar
(in the same way the aldehydes and
ketones were).
110.
The Amines + Amides both
contain NITROGEN.
111. Count to 3 for nitrogen,
N must always make
3 bonds.
112.
Amines are always found in
the middle of a chain
114.
Amides are always found on
the end of a chain.
Location, location, location!
115. AMINES
116. AMIDES
R’
O H
R―N―R”
R―C―N―H
The nitrogen atom is in the center
of three “R” groups.
In college organic chem, these
would be three hydrocarbon
chains of any length. In our class,
the R’ and R” groups will always
be hydrogen atoms..
These groups are always at the end of a
chain, and the nitrogen is attached to a
carbon which is also attached to an oxgyen.
Although the “N” could have 2 chains, it will
only have 2 hydrogen atoms in our class.
Amides for us will be
Amines can be attached to any
carbon in a chain.
Amines for us will be R―NH2
O
H
R―C ―N―H
117. Draw
4-octanamine
and hexanimide
4-octanamine
C
C
C
C
C
C
C
C
N―H
H
117.
O
C
C
C
C
C
C
N―H
H
hexanimide
OC Class 6
OB: Examining and Mastering the
Organic Chemical Reactions:
Substitution, Addition,
Fermentation, Esterfication,
Polymerization, and Saponification.
We have seen substitution reactions last week when we discussed the formation of
halocarbons. We need to stick halogens (F, Cl, Br, or I) into a saturated hydrocarbon.
Being saturated, there is NO ROOM for any new atoms, so we need to substitute in one
halogen atom for a hydrogen atom.
118. Substitution reactions:
Saturated
Hydrocarbon
(alkane)
Propane
+
+
+ Halogen
(F, Cl, Br, or I)
F2
+ F2
Halocarbon + HX
(X = halogen atom)
1-fluoropropane + HF
Saturated
Hydrocarbon
(alkane)
Propane
+ Halogen
+
+
(F, Cl, Br, or I)
F2
+ F2
118.
Halocarbon + HX
(X = halogen atom)
1-fluoropropane + HF
F + HF
Draw these 2 substitution reactions with structural
diagrams and NAME the products properly.
119. Ethane + chlorine yields…
120. Butane + iodine yields 2-iodobutane + HI
Do these 2 substitution reactions…
119. Ethane + chlorine yields chloroethane + HCl
+ Cl2
Cl + HCl
120. Butane + iodine yields 2-iodobutane + HI
+ I2
+ HI
I
121. For ADDITION reactions, we’ll start with a
halogen and a NON-SATURATED hydrocarbon, an
alkene or alkyne. We will ADD the halogen into it
122. Let’s draw and wrote the word equation for:
Ethene + Bromine yields 1,2 dibromoethane
For ADDITION reactions, we’ll start with a halogen
and a NON-SATURATED hydrocarbon, an alkene or
alkyne. We will ADD the halogen into it
122. Ethene + Bromine yields 1,2 dibromoethane
+ Br2
Br Br
The double bond opens, a bromine is added to each carbon (not onto 1 carbon)
A triple bond would open into a double bond, and you’d add the Br the same way.
123. Draw: Propene and chlorine → 1,2 dichloropropane
124. Ethyne and fluorine → 1,2 difluoroethene
123. Propene and chlorine yields 1,2 dichloropropane
Cl
+ Cl2
Cl
124. Ethyne and fluorine yields 1,2 difluoroethene
F F
+ F2
H—C=C—H
Fermentation is a chemical process known to
humans for thousands of years. It turns fruit
juice, or vegetable juice into ethanol and carbon
dioxide. It’s how to make champagne, or wine, or
beer, or even stronger liquors.
It’s a billions of dollars a year industry
around the world, it’s wonderful in
small amounts when you’re over 21, and
it can be terrible too. Devastating.
It’s not good for any one, your body
must process this ethanol away as a
toxin. It can change your life into hell
if you drink too much of it. It will
change the way you think, and it is not
as casual as most teenagers think.
Don’t drink until you’re 21. Never ever
drive or go driving with someone who
has been drinking. Ever, anyone, no
matter what.
125. Fermentation is the organic
chemical reaction that turns sugars
into ethanol and carbon dioxide by
way of yeast enzymes.
126. This is not a reaction that
happens outside of the yeast.
Yeast excrete waste products called
ethanol and CO2, by anerobic respiration.
128.
Sugars
yeast enzymes
in water
CH3CH2OH + CO2
129. Polymerization the process of making plastics.
At right is a clip from the movie
“The Graduate” with Dustin Hoffmann
(he’s the guy on the left).
That other man is saying to Ben (who just
graduated from college) “I have just one
word of advice for you.”
“Are you listening to me Ben?”
“Yes.“ Ben replies. So he says:
“Plastics.”
130.
Polymerization
poly
means
many
mer
means
unit
or body
-ization
means the
process of
the organic chemical reaction of making plastics or polymers.
131. A lot of…
ethene molecules
n
can form long chains
of a polymer called
polyethene
catalyst
catalysts break open those
double bonds, allowing the
“mers” to unite into chains that
go on and on, and are indefinite
in length. There is not a “real”
formula for the polymer formed.
the polyethene formula is
(-CH2CH2-)n
Other plastics that you probably know of already are
132. PVC, or polyvinyl chloride is the OLD FASHIONED
name for the plastic white pipes made in Vestal, and used
for plumbing in your home. It starts out with CH2=CHCl as
the “mer”. You’d call this chloroethene.
133. Polyethylene is what thin, soft clear plastic
food bags are made of
(look at your sandwich bag).
134. Polystyrene (Styrofoam) is another plastic
you have used. This one is white + opaque.
135. Different plastics, different
properties. They all start with
billions of identical “mers” and
form polymers with unique
properties.
136. Teflon (used in frying pans) is Polytetrafluoroethylene.
The “mer” is CF2=CF2 which you’d call
1,1,2,2 tetrafluroethene.
(technically the 1,1,2,2 is unnecessary, there are no
other places to put the 4 fluorine atoms)
137. CH2=CCl2 is the mer that makes
Saran wrap (thin clear food plastic).
you’d call it 1,1 dichloroethene.
138. Esterfication is when an acid + an alcohol form
an ester (and water).
Acid + alcohol yields an ester + H2O
139. we will combine propanoic acid + ethanol
(draw structural diagrams for this now)
Acid + alcohol yields an ester + H2O
139. we will combine propanoic acid + ethanol
+
OH
HO
H
H
C
C
H
H
H
Acids will ionize the hydrogen in the –COOH group. Alcohols do not
ionize at all. To form water, something a bit odd happens.
The OH in the -COOH group combines to the H in the -OH group of
the alcohol to make the water HOH.
The rest of the molecules squeeze into a big molecule, the ester.
Acid + alcohol yields an ester + H2O
we will combine propanoic acid + ethanol
+
HO
OH
H
H
C
C
H
H
H
This OH and H makes the water.
140. the rest of the 2 molecules go together like this:
+ HOH
Ethyl Propanoate
141. Draw the reactant molecules and product molecules
(and product names)
butanoic acid + 1-propanol form an ester + water
141.
butanoic acid + 1-propanol form an ester + water
+
HO
H
H
H
C
C
C
H
H
H
H
OH
+ HOH
Propyl Butanoate
I use
that
stuff
142. SAPONIFICATION is the most complex reaction
but the easiest to recognize and remember. If you misspell
the reaction the first four letters might spell out SOAP.
In fact, this organic reaction is the reaction that makes SOAP.
(the take a bath kind) Did I say SOAP?
+ 3 NaOH
Note, a fat like this
contains 3 ester groups,
this is a triple ester
You can use any 3
bases, different
bases will result in
different kinds of
soap, softer, harder,
liquid or solid,
different colors, etc.
The products of saponification are a triple alcohol
(you have heard of glycerol, and soap. Note, the
soap has a “triple” molecular shape, and contains
an ION as well.
This ion makes it better able to break up surface
tension in water (remember those bugs?)
+ 3CH3(CH2)14CO2Na+
We don’t have to name these
molecules, just “recognize” them
at the end of this equation.
Organic Chem Class #7
OB: Branched Hydrocarbons
Drawing them, naming them,
and ISOMERS TOO.
We’ll need lots of paper, and your thinking caps on.
We’ve learned that ISOTOPES are chemically identical
atoms with different atomic masses (different
numbers of neutrons) which are the reason for
average atomic masses being decimals.
We’ve learned about ALLOTROPES, such as graphite
and diamonds, both pure carbon, but bonded
differently and with different properties. If you don’t
believe that, try to take the regents with a diamond,
or get engaged with a pencil!
144. ISOMERS are organic compounds with the same chemical
formula, but different structures, so they have the same
molar mass, but totally different properties.
145. Examples are ethanol and dimethyl ether
What are the structural formulas +
the chemical formulas for these 2 molecules?
Condensed
Chemical
structural
formulas
formulas
Ethanol
Dimethyl
ether
145. Examples are ethanol and dimethyl ether
What are the structural formulas +
the chemical formulas for these 2 molecules?
Chemical
formulas
Ethanol
CH3CH2OH
Dimethyl
ether
CH3OCH3
Condensed
structural
formulas
C2H5OH or
C2H6O
C2H6O
Branched hydrocarbons will also be isomers. Count
the carbon atoms, if all the bonds are single bonds,
then equal numbers of carbons will be isomers even
though the molecules are “different”.
146A. Draw hexane
146B. Draw 2,3-dimethyl butane.
146A. Draw hexane and draw 2,3-dimethyl butane.
CH3
There’s a methyl group
hanging off of the
#2 and the #3 carbon.
It is an isomer to hexane.
CH3
147. Count carbons and count hydrogen atoms in the
above 2 molecules.
Do they have the same chemical formulas? ________
Same number of Carbons? _______
Same number of Hydrogens? _______
These 2 molecules are called _____________________
of each other.
They have different physical structures + different
properties but the same _____________________.
148. Draw pentane + 2methylbutane.
Are these isomers?
148.
Isomers?
YES!
149. Draw 3-ethyl hexane
150. 3methyl-4,5-dibromo hexane
151. Draw 7ethyl, 8-fluoro, 2nonyne
152.
Draw all the pentane isomers, and name them,
what is the chemical formula for pentane?
n-pentane (or normal pentane)
methylbutane
dimethyl propane
-C-C-C-C-C-C-C-C-C-C-
-C-C-C-C-C-
Time to draw
two posters…
Organic Chem Class #6b
OB: the mastering of organic esterification reactions + the rest of them
Each student will choose an organic acid (1-10 carbons long), plus an
alcohol (1-10 carbons long, make sure it’s a #1 alcohol please), and form
HOH plus the proper ester. We’ll draw these neatly with color pencils
(as practiced together first),
Then we’ll choose one more reaction (addition, substitution,
fermentation, polymerization, or saponification) and draw out one nice
looking example. All drawings will be reviewed as a classwork grade,
and the best ones will be added to the website for review purposes.
Esterification: the chemical reaction between an
organic acid + an alcohol to form an ester (and H2O).
Choose 1-10 acid and alcohol.
I choose pentanoic acid and methanol alcohol.
Draw acid first, “facing” the alcohol,
the alcohol is to be drawn HO- side facing the acid.
Pentanoic Acid
+
Methanol
yields
HOH
CH3CH2CH2CH2COOH + HOCH3
+
Methyl Pentanoate
HOH + CH3CH2CH2CH2COOCH3
O
C
C
C
C
+
C
HO
OH
O
C
C
C
C
C
O
C
C
HOH +
You must choose an acid and an alcohol and draw a
full page diagram for it. Label it with words, and
condensed structural formulas.
(you can’t choose mine, and don’t choose methyl methanoate
because you’re too lazy to draw a few extra carbons + hydrogen
atoms. We need a full mix if possible.
Then choose one other reaction, run it by me, then
make a second poster as well.
Finally, finish up the reactions and drawings for
your organic lab report today.