Chapter 11

Organic chemistry
Organic compound: Any compound where at least one direct C—H bond is found.

~ Unique properties of carbon:

It’s the only element that forms a chain of bonding with itself, this property helps
carbon form a wide range of different compounds. The type of bonding for carbon
is covalent bonding and its valency is 4.
Note: carbon has to form 4 bonds.
Carbon as an element has different forms: graphite, diamond, nanotube of
fullerene.
Organic compounds in everyday life: DNA, RNA, protein, carbohydrates, hair,
plastics…
A short test to separate organic compounds from mineral compounds:
When an organic compound burns, a black ash (carbon) forms whereas mineral
compounds are mostly not combustible so if they burn, a white ash forms.
Ex) Plastic/sugar after burning give a black substance whereas magnesium forms a
white powder.

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  Functional groups:
A group of atoms covalently bonded to each other which is common for a class of
organic compounds. For example, C—O—H  if you see this structure its
alcohol.
1. Alkane: only made up of carbon & hydrogen – all bonds are single (no
functional group).

2. Alkene: a double bond between two carbons

3. Alcohol: a single bond between C, O & H

4. Carboxylic acid:

5. Amine: this class are derivates of ammonia (itself is mineral).

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 Note: By replacement of at least one H in ammonia with a carbon, amines
are produced.
6. Amide:

7. Ester:

Find the functional groups in the following organic compounds.

Note: The difference between carboxylic acid & ester is a C & a H.

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 Classification of organic compounds based on saturation
Saturated: if there’s no double/triple bond or ring, just single bonds.
Example) alkane, alcohol, amine
Unsaturated: any compound which has a double bond, triple bond/ring.
Example) alkene, carboxylic acid, amide
Different form of writing compounds

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Naming organic compounds:
1. Alkanes:
Step 1) we should find the longest consecutive carbon chain.
Note: the longest chain could be straight or bent
Step 2) Numbering the longest chain, there are 3 criteria for numbering:
i. From any side which is closer to the branch
ii. If (i) doesn’t work, from any side that has more branches
iii. If (i) & (ii) don’t work, from any side that’s branch has the prior alphabet
Step 3) first we name the branches, based on the alphabetic order, then the
backbone.

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Naming of branches are based on roman numbers, the first 4 carbons have their
own specific names, but the rest are exact roman numbers.
Number of 1 2 3 4 5 6 7 8 9 10
carbons
Stem meth eth prop but pent hex hept oct nona deca

Ending ane ene ol Oic acid Amine Oate

Functional Alkane Alkene alcohol Carboxylic Amine Ester
groups acid
Example methane Ethene Alkanol Ethanoic Methyl Propanoate
acid amine
Criteria 3 example)

Note: we must show the position of branches & some functional groups that are
not clear. (Carboxylic Acid is always placed at the end of the backbone so theres
no need to refer to their position.)
- there are no other options
for the position of branches, so
there is no need to write 2 before.

Note: methyl can never be on the first or last branch.

When naming, if we can remove any extra numbers from the name we will.

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Note: If there are more than one branch, we have to show all of them together
using the prefix di, tri, tetra.
Note: If halogens are branched, they’ll end in ‘o’.

2. Alkenes:
Every rule is the same except for these 2:
Note 1: The functional group must be in the backbone and numbering is
from any side which is closer to the functional group.
Note 2: The ending of the backbone must be ‘ene’ & the position of the
functional group must be mentioned in the backbone.

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3. Alcohol:
Every one of the rules are like the previous rules except for these 2:
Note 1: The functional group must be in the backbone and numbering must
be closer to the functional group.
Note 2: The ending of the backbone should be ‘ol’ & the position of the
functional group must be mentioned in the backbone.

4. Carboxylic acid
Every rule is the same except for these 2 notes:
Note 1: The functional group must be in the backbone and numbering must
start from the functional group.
Note 2: There’s no need to mention the position of the functional group as
its always number 1 (at the end), it ends with ‘oic acid’.

5. Esters:
First we find the ester link, then we divide the ester into 2 parts, the
alcoholic part will be branch ending with ‘yl’ whereas the acid is the main
chain ending in ‘oate’.

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Isomerism: when molecules have the same molecular formula but a different
structural formula.

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 All classifications of organic isomerism

Chain

Structural Positional

Functional

Cis
Isomers
Geometric
Trans

Enontiomer
Optical
Deastromer

~ Chain isomerism: backbone or position of branches are different.

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~ Positional isomerism: position of the functional group will be different in the
backbone.

~ Functional isomerism: closed molecular formula is the same but 2 different

functional groups appear.

Exercises- State the isomers of the following:

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~ Draw all the structural isomerism’s of C4H9OH:

Question: Find the different type of isomerism’s for the molecules above.
A & B = positional B & D = chain
B & C = chain A & D = chain
C & D = positional A & C = chain
Organic reactions
1. Alkane:
1. Combustion

2. Free radical
Alkane substitution

3. Cracking
1 Combustion: Alkane + O2  Water + CO2
If oxygen isn’t enough, incomplete combustion takes place so instead of
CO2, two other products may form (C or CO).
Ex) CH4 + 2O2  CO2 + 2H2O (complete)
Ex) CH4 + O2  CO / C + H2O (incomplete)
2 Free radical substitution: alkane + halogen  halogeno alkane + acid

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3 Cracking: long hydrocarbons in the presence of a catalyst Al2O3 or SiO3 &
absence of O2 are heated to crack, forming 3 sets of products:

2. Alkene:
addition of H2O

addition of X2
1. Combustion (X being Cl, I,
Br...)

addition of HX
Alkene 2. Addition
(In AS)

3. Oxidation addition
polymerisation

addition of H2

1 Combustion: alkene + O2  CO2 + H2O

2 Addition: addition means the double bond breaks & something will be
added to the double bond.

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Addition polymerization: a process In which monomers form covalent bonds with
each other to become a long chain (polymer).
Monomer: building block of polymer is monomer.
Repeating unit: a repeating pattern in the backbone of polymers that represents the
structure of a monomer.
~ Different monomers in addition polymerization:

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 3. Alcohol:
1A. Addition of
steam to ethane
(industrial method)
1. Formation
1B. Fermentation of
glucose
2. Combustion

Alcohol

3. Oxidation of 1-ol

4. Esterification
1 Formation:
 Addition of ethene to steam was discussed in alkenes.
 Fermentation (1B) :

Note: Yeast is the catalyst (biological catalyst) for this reaction.

Note: As the % of ethanol reaches 14%, it kills yeast, so the maximum % of
ethanol in a mixture is 14%.
Note: To extract ethanol from the mixture, first we must do filtration then
we should do fractional distillation.

-CO2 can exit the air lock but O2 & N2 cant enter the airlock (since there is no
pressure from their side).
Comparison between the industrial & fermentation method of forming ethanol:
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Ethanol by the hydration of ethene Ethanol by fermentation

Originates from a non-renewable source Made from readily renewable sources

(petroleum)
Small scale equipment capable of Relatively simple, large vessels
withstanding pressure
A continuous process A batch process – need to start over
each time
A fast reaction rate Relatively slow process
Yields highly pure ethanol Ethanol must be purified by subsequent
distillation – fermented product can be
used as it is for some purposes
A sophisticated, complex method A simple, straight-forward method
High yield Low yield
2 Combustion: alcohol + oxygen  carbon dioxide + water

3 Oxidation of 1-ol: 1-ols in the presence of oxidizing agents convert to carboxylic

acid (alcohol to acid).

We can use K2Cr2O7 & KMnO4 as an oxidizing agent.

The color change if from purple to very light pink (KMnO4 is purple).
K2Cr2O7 is orange and then green after oxidation.
Note: as we add oxidizing agent, it needs heat to do the oxidation reaction.

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4 Esterification

Note: H2SO4 is the catalyst & we need heat & reflux to do esterification/to form
ester.

Hydrolysis of Esters: Esters in acidic conditions can be hydrolyzed to alcohol &

acid.

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~ For hydrolysis: we should find the ester link, then cut the ester link & finally add
‘H’ to the alcoholic part & ‘OH’ to the acidic part.

Ester Smell/flavor
Ethyl 2-methyl butanoate Apple
3-methyl butyl ethanoate Pear
1-methyl butyl ethanoate Banana
Butyl butanoate Pineapple
Octyl ethanoate Orange
Methyl propyl methanoate Raspberry
Pentyl butanoate Strawberry
~ No need to memorize the table ~

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 4. Carboxylic acid:

1. Formation by oxidation of 1-ols

Carboxylic acid
2. Esterification

3. Reaction with bases

Bases: Metal oxide, metal hydroxide, metal carbonate, metal hydrogen carbonate
Reactions with bases:

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 Addition
(discussed in 1. Polyester
alkenes)
Polymerisation

Condensation 2. Polyamide

3. Polysaccharide

 (1) Polyester: functional group of ester will be repeated in the

backbone/chain of the polymer.

 (2) Polyamide: functional group of amide will be repeated in the chain of the
polymer.

 (3) Polysaccharide: different sugars will form bonds together & structure
like C—O—C will form in the backbone/chain of the polymer.

Forming polyester:
We need to add di-ol & di-oic acid & then alcohol & then carboxylic acid will
react with each other to form polyester.
Note: we should remove the ‘H’ from alcohol & ‘OH’ from the acid to form the
ester like.

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To find monomers from the polymer (polyester), first we should find the ester link,
then we add ‘H’ to alcohol parts & ‘OH’ to the acidic part.
Example of polyester: terylene is the trade name for the polyester.

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Note: if we have a monomer that has 2 active ends, 1-ol, 1-acid, this monomer
itself can be polymerized.

Forming polyamide:
There are two monomers, one is di-amine & the other is di-oic acid, then by
forming peptide links, they form a polyamide.

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Note: Amino acids  if there are amine & carboxylic acid functional groups on
one monomer, then this monomer itself can form polyamine.

Forming polysaccharides:
The building blocks for polysaccharides are simple sugars like glucose.

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Notes for all condensation polymers:
All of these condensation polymers can be hydrolyzed to form their monomers, in
both basic & acidic media.
Hydrolysis: using water to break a compound.
We break down polyamide, polyester, & polysaccharide from their compounds to
form their monomers, during this process water is used.

Biodegradable: something which can be broken down by microbes. Example of

biodegradable substance is condensation polymers.
Photodegradable: something which can be broken down by light.
Hydrocarbon: any compound which only contains carbon & hydrogen
Homologous series: a family of organic compounds which has the same general
formula, same functional group & similar chemical properties.
Example) alkanes, alcohols
Note: In each homologous series, by increasing the number of carbons, boiling &
melting points increase.
There are 3 major sources of fossil fuels: coal, petroleum & natural gas.

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 - Crude oil is a mixture of hydrocarbons & by fractional distillation, different
fractions will be separated.

- Temperature is least at the top & highest at the bottom.

⭐ Refinery gas is mostly methane (90%)
- Fractions are separated by boiling points.
⭐Viscosity: the tendency of liquids against flowing
Example) Honey is more viscous than water.

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⭐Viscosity increases down the tower.
⭐Viscosity also increases as the number of carbons in a hydrocarbon increase.
- Petrol is just one segment of petroleum.

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