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All Organic Compounds
Hydrocarbons
Standard Hydrocarbons
with CxHx
Hydrocarbon Derivatives
Hydrocarbons..(C’s and
H’s) BUT ALSO other
elements.
Organic Halides: are when 1 or more hydrogens have been replaced by a
halogen (Group 17; F, Cl, Br, I)
The element itself (Organic Halide) is its own functional group and is
named the same as any other branch group.
1
2
Practice (Easy)
7
6
5
4
3
2
1
***Name the side branches alphabetically just like
with ethy and methy, etc.***
Practice (Cyclo/Benzene)
This type of reaction occurs when UNSATURATED
hydrocarbons
react with diatomic molecules like;
H2
Cl2
Br2
I2
HBr
HCl
HI
The addition of these diatomic molecules saturate the hydrocarbon…..breaks the
double or triple bonds and adds
BOTH onto the chain.
H
H
***Addition of H2 breaks the double bond and adds the
hydrogens onto the hydrocarbon.***
Step 1
H
Cl
***For every diatomic molecule you add to a
UNSATURATED hydrocarbon it break a bond…so
it breaks the “unsaturations” step by step.***
H
Cl
Step 2
H
Cl
2, 2 – dichloropropane
This type of reaction occurs when SATURATED
hydrocarbons react
with diatomic molecules like;
H2
Cl2
Br2
I2
HBr
HCl
HI
The substitution of these diatomic molecules trade places with hydrogens already in the
adds ONE
hydrocarbon…..breaks the SINGLE BOND and
onto the chain.
The second joins with substituted element and forms another compound that leaves the
hydrocarbon chain.
Cl
Just indicates a common
catalyst…DOES NOT
MAKE A
DIFFERENCE!!!
Adding an alcohol(OH-) Functional Group to a hydrocarbon
drastically changes the properties of the hydrocarbon.
Such as;
1. Higher Solubility in water.
2. Increased boiling point .
3. Short-Chain alcohols (less than 3 C’s are VERY soluble.
4. Long chain alcohols (more than 5) are slightly soluble.
Methanol and Ethanol
Methanol (CH3OH) AND Ethanol (CH3CH2OH) are the two
most common alcohols.
***Because Methanol and Ethanol only differ from one
another by a “CH2” they are part of a “homologous
series”.***
Homologous Series:
A series of compounds that only differ by a single repeated “group”.
CH3OH CH3CH2OH CH3CH2CH2OH
Methanol
Ethanol
Propanol
CH3CH2CH2CH2OH
Butanol
Alcohol…
Alcohol was is made by fermentation (yeast, baking,
making bread).
Alcohol is poisonous, the “drunk” feeling is the feeling of
being poisoned.
The disorientation and loss of motor functions (stumbling)
is because YOU ARE BEING POISONED!
Ethanol CH3CH2OH is the ONLY alcohol that wont
outright kill you.
So…..
DON’T TRY TO MAKE IT….IT COULD BE WRONG.
Alcohol…
Alcohol added to fuel to help it burn more efficiently.
Alcohol often added to fuel to as gas line antifreeze.
CH3OH (methanol) is TOXIC.
Add methanol to Ethanol (alcohol you could drink) makes
IT TOXIC TOO.
Ethanol used in;
Lacquers.
Varnishes.
Perfume.
Synthetic Flavours.
Naming Alcohols
Hydrocarbons that contain alcohols are named THE SAME way as usual.
1. You name the longest parent chain.
2. You use –ane –ene –yne for single, double, triple bonds.
**You number the hydrocarbon ‘Parent Chain” so branches are on lowest carbon
numbers**
**Number the carbons so ALCOHOL is on the lowest number possible**
3. You add “–ol” on the end of a hydrocarbon to show an alcohol (OH) functional
group is present.
H HH HH HH
H-C-C-C-C-C-C-C-OH
3
2 1
7
5
4
6
HH H H H HH
7 Carbons long
All single bonds
Number carbons so OH on lowest number.
Heptan -1- ol
Heptanol
***Its very common to just NOT put -1- for alcohols on the end of hydrocarbons***
Multiple Alcohols
***When there is more than 1 alcohol functional group in a
hydrocarbon you describe it the same as you would if there
were multiple F’s or Br’s (Halide groups).***
Diol -----2
Triol-----3
***Make sure if you use “di” you have listed two
places….1,2 or 2,5..3,4…etc****
***Make sure if you use “tri” you have listed three
places….1,2,3 or 2,2,5..3,5,5…etc****
Practice
H OH H H H
-H--C--C--C--C--C--H
4
3
2
1
5
5 Carbons long
H H H OH H
Number carbons so double bond on lowest number.
A DOUBLE BOND!!
Pent -1-ene -2,4- diol
Alcohol groups on 2 different carbons.
State which carbon alcohol groups are on.
Alcohols
Primary, Secondary, Tertiary
Whether an alcohol containing hydrocarbon is considered primary, secondary, or
tertiary is dependant on the Carbon that the OH group is attached to.
H H H H H
H--C--C--C--C--C--OH
Carbon connect to ONE
other carbon makes it
primary.
H H H H H
The carbon that the OH group is attached to
make this a primary alcohol.
Alcohols
Primary, Secondary, Tertiary
Whether an alcohol containing hydrocarbon is considered primary, secondary, or
tertiary is dependant on the Carbon that the OH group is attached to.
H H H OH H
H--C--C--C--C--C--H
Carbon connect to TWO
other carbon makes it
secondary.
H H H H H
The carbon that the OH group is attached to
make this a secondary alcohol.
Alcohols
Primary, Secondary, Tertiary
Whether an alcohol containing hydrocarbon is considered primary, secondary, or
tertiary is dependant on the Carbon that the OH group is attached to.
Carbon connect to
H H OH H H
H--C--C--C--C--C--H
H H
H H
H --C-- H
H
THREE other carbon
makes it secondary.
The carbon that the OH group is attached to
make this a Tertiary
alcohol.
Alcohols
Combination Practice
Whether an alcohol containing hydrocarbon is considered primary, secondary, or
tertiary is dependant on the Carbon that the OH group is attached to.
5 Carbons long.
H H OH H H
H--C--C--C--C--C--H
5
4
H H
3
2
1
H H
H --C-- H
All SINGLE bonds.
OH on carbon 3.
CH3 group (methyl) on carbon 3.
H
3-methyl pent an-3-ol
Practice Cyclo/Benzene
Alcohols
OH
OH
OH
OH
Cyclopentane-1,2-diol
Or
O-cyclopentane-diol
Cyclohexane-1,3-diol
Or
M-cyclohexane-diol
Practice Cyclo/Benzene
Alcohols
OH
OH
Cyclopentane-1,2-diol
Or
O-cyclopentane-diol
Elimination Reactions
It is often very useful to be able to create alkenes and alkynes
from alkanes.
This can be done in TWO ways;
1. Ethene
produced from
Ethane Cracking
2. Ethene
produced by
Ethane
Elimination
Reactions.
Ethane cracking is a special hydrocarbon cracking in which Ethane
(single bonded-Saturated) is “cracked” into Ethyne (double bondedunsaturated).
Elimination and Addition Reactions
***Elimination reactions are also called Dehydration
reaction because they UNSATURATE a hydrocarbon
and produce water as a second product.***
H H H H H
H2SO4
H--C--C--C--C--C--OH
H3PO4
H H H H H
Pentanol
H H H H
-H--C--C--C--C--C
H H H H
Pentene
H
H
+ H 2O
Elimination and Addition Reactions
***Elimination reaction are also called Dehydration
reaction because they UNSATURATE a hydrocarbon
and produce water as a second product.***
H H H H H
H--C--C--C--C--C--H
H H H Cl H
2- chloropentane
Cl- + H2O
+
+ KOH
NaOH
H H H H H
-H--C--C--C--C--C--H
H H
H
Pent-2-ene
Elimination and Addition Reactions
***Addition reaction are also called hydration
reactions because they SATURATE a hydrocarbon
by adding water as a reactant.***
H H H
-H--C--C--C--H
+ HOH
H
Propene
H H H
H--C--C--C--H
H OH H
Propan-1-ol
It is the exact opposite of a hydration reaction. The double or
triple bond is broken and the H and OH group are added onto
the carbons to keep the 4 bonds rule.
Alcohols and Elimination Reactions
Functional Group: -OH (hydroxyl group)
• Drop the “e” from the end of the alkane, alkene, or
alkyne and add -ol
• If necessary add the number of the carbon the –OH
group is on; eg., propan-1-ol and propan-2-ol
• If there are more than 1 OH you keep the whole
name (KEEP THE “E”) use “di” or “tri” “ol” instead.
Alcohols and Elimination Reactions
Preparation:
If you react an alkENE with water (hydration reaction) it will
break the double or triple bond and add “H” and “OH”.
H H H
H H H
-H--C--C--C--H
H
Propene
+ HOH
Water
H--C--C--C--H
H OH H
Propan-1-ol
Alcohols and Elimination Reactions
Elimination Reactions:
(Dehydrations)
• The opposite of an addition (hydration) reaction. An Alcohol
is unsaturated creating a double bond and H2O.
General Formula:
H2SO4
H H
R-C = C-R
H3PO4
+ HOH
Alcohols  alkene + Water
H H
R-C—C-R
H OH
Alcohols and Elimination Reactions
Elimination Reactions:
(Organic Halide (OH-/Basic)
• The reaction of hydrocarbons containing a halide (F, Cl, Br, I)
with an OH- group (basic environment)
General Formula:
Organic Halide + OH-  Alkene + Halide ion (Cl-) + Water
H H
R-C—C-R
H Cl
+ OH-
H H
R-C = C-R
+ HOH
+ Cl-
A functional group consisting of; a double bonded oxygen and OH groups
bound to end carbon of a hydrocarbon.
***Can be attached to ANY
hydrocarbon chain***
Carboxylic acid naming is done the same as a normal hydrocarbon EXCEPT at the
end of the hydrocarbon name you add “–oic acid”
Methane
Methanoic Acid
Butane
Butanoic Acid
A functional group consisting of a single bonded O between TWO carbons
and double bonded O.
Named by counting the number of carbons on the =O side and changing the ending
to “–oate”.
Methyl ethane
ethanoate
You name the second half of
the ester (side without =O)
like a alkane branch ending
in “–yl”
The Ester Functional Group
***Esters are often added to foods for artificial
flavours.***
Making an Ester
(Esterification)
***An Ester is formed when a carboxylic acid
(COOH) reacts with an alcohol (COH) and
undergoes a condensation reaction (dehydration).***
Ethanol
Butanoic Acid
H
+
OH  HOH (Water)
Making an Ester
(Esterification)
***An Ester is formed when a carboxylic acid
(COOH) reacts with an alcohol (COH) and
undergoes a condensation reaction (dehydration).***

Ethyl butanoate
+ H2O
Ester Formation Summary
CH3-C-C-OH
+
O
=
HOH
=
O
HO-CH
O-CH33  CH3-C- O-CH3
Methylethan oate
Esterification and Benzene Rings
***Esterification when benzene rings have the required
carboxylic acid and hydroxyl groups.***
Esterification and Benzene Rings
***Esterification when benzene rings have the required
carboxylic acid and hydroxyl groups.***
The common plastics around you are formed from single unit
monomers linked together into longer chains called
polymers.
Monomer Monomer Monomer
Polymer
**Addition polymers form from alkene or alkyne monomers.**
Example 1: Polypropene (Propylene)
Again the joining
of the monomers
breaks the double
bonds and connects
the monomers
together.
Propene monomer “sub” units
General Formula
Example 2: Polyvinyl Chloride
Viny chloride monomer “sub” units
Again the
joining of the
monomers
breaks the
double bonds
and connects
the monomers
together.
General Formula
Example 3: Polystyrene
Again the joining of
the monomers breaks
the double bonds
and connects the
monomers together.
Styrene monomer “sub” units
(Styrofoam)
General Formula
Example 4: Teflon
Again the joining of
the monomers breaks
the double bonds
and connects the
monomers together.
tetrafluoroethene monomer
“sub” units
General Formula
Condensation polymers are made in a similar way to addition
polymers as BOTH polymers are formed from monomer
“sub” units.
O
=
=
O
OH-C-CH2-CH2-C-OH
Butane-1,4-dicarboxylic acid
+ OH-CH -CH -OH
2
2
Ethane-1,2-diol
***Just like in esterification, an HOH is removed when they
join together***
***BUT, in condensation polymers the “sub” unit are
alternating “double ended” carboxylic acids and alcohols
forming “ester” linkages.***
O
=
=
O
HOH
OH-C-CH22-CH22-C-OH
-C-O
Butan-1,4-dicarboxylic acid
2
2
Ethan-1,2-diol
O
=
=
O
-CH -CH -OH
+ OH-CH
+ HOH
-C-CH2-CH2-C-O -CH2-CH2-On
General Formula
***You ARE NOT expected to be able to name this***
Example 1: Lipids
+ 3 Fatty Acids
+ 3 HOH
Example 1: Polyester (Synthetic Lipids)
O
=
=
O
OH-C-CH2-CH2-C-OH
Butane-1,4-dicarboxylic acid
+
OH-CH -CH -OH
2
2
Ethane-1,2-diol
O
=
=
→
O
+ HOH
-OH-C-CH2-CH2-C-O- CH2-CH2n
Example 2: Protein Synthesis( P + P = Amino)
(Acids)
H
+
Glycine
(Amino Acid)
No need to
memorize
→
=
O
H
=
=
N-CH2-C-OH
O
N-CH-C-OH
H
CH3
**The bond between
two amino acids is
Alanine
(Amino Acid)
called a PEPTIDE
bond**
O
=
O
H
+ n HOH
-N-CH2-C-O- N-CH-C-OH
H CH3
Protein Segment
n
Water
Example 2: Nylon( Synthetic Amino Acids)
The same as peptide bonding, EXCEPT no Amino Acids, just
alternating “double ended” COOH (carboxylic acid) subunits
**The bond between
and “double ended” NH2 (Nitryl) subunits”.
two Nylon
molecules is called
a AMIDE bond**
“Double Ended” COOH
“Double Ended” NH2
+ n HOH
→
Water
n
Example 2: Kevlar( Synthetic Amino Acids)
The same as peptide bonding, EXCEPT no Amino Acids, just
alternating “double ended” COOH (carboxylic acid) subunits
and “double ended” NH2 (Nitryl) subunits”. AND THERE IS
HYDROGEN BONDING BETWEEN POLYMER CHAINS!
O
=
=
O
OH-C-
-C-OH
+
“Double Ended” COOH
=
→
H
-N
N-
H
H
“Double Ended” NH2
O
=
O
H
-C-
-C- N-
H
-NH
+ n HOH
n
Example 2: Kevlar( Synthetic Amino Acids)
H
=
O
=
O
-C-
-C- NH
-N -CH
O
-N -CH
=
O
-C- NH
-N
H
O
=
-C- N-
=
-C-
O
=
=
O
=
O
-C- N-
H
****When multiple polymers line up they hydrogen
bond to each other making the polymer even
stronger.***
-N
H