Organic Chemistry

Classify the following compounds as organic

or inorganic:
•Sugar •Sulfuric acid
•Water •Putrescine
•Carbon dioxide •Cadaverine
•Vanillin •Calcium chloride
•Formaldehyde •Limonene
•Salt •Cinnamaldehyde
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Characteristics of Organic Compounds
Common Features

1. All organic compounds contain carbon atoms and

most contain hydrogen atoms.

•Carbon always forms four covalent bonds.

•Hydrogen always forms one covalent bond.

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Characteristics of Organic Compounds
Common Features

2. Carbon forms single, double, and triple bonds to

other carbon atoms.

9
Characteristics of Organic Compounds
Common Features

3. Some compounds have chains of atoms and some

compounds have rings.

10
Characteristics of Organic Compounds
Common Features

4. Organic compounds may also contain elements

other than carbon and hydrogen.
•Any atom that is not carbon or hydrogen is called
a heteroatom.
•Each heteroatom forms a characteristic number of
bonds, determined by its location in the periodic
table.
•The common heteroatoms (N, O, F, Cl, Br, and I)
also have nonbonding, lone pairs of e−, so that
each atom is surrounded by an octet of e−.
# of bonds + # of lone pairs = 4
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INORGANIC COMPOUNDS

• High melting and boiling point

• Generally soluble in water and rarely soluble in
nonpolar solvents
• Conduct electric current
• Inflammable
• Ionic bonding
ORGANIC COMPOUNDS

•Low melting and boiling point

•Most are not soluble in water but are
generally soluble in nonpolar solvents
•Do not conduct electric current
•Generally flammable
•Covalent bonding
Allotropes of Carbon

• Graphite
• Diamond
• Amorphous Carbon
• Fullerenes
•Types of Organic Formulas
•Molecular formula
•Expanded structural formula
•Condensed structural formula
•C6H14

•CH3 – CH2 – CH2 – CH2 – CH2 – CH3

• Isomers – organic cmpds with the same molecular
formula but with diff. bond orders

16
17
Structural Formulas
A 2D model shows bonding patterns and
shapes of molecules
H
H C H
Carbon is found in the center
H
The short line – represents a
pair of electrons.
 Types Of Bonds
Single Bond – single covalent bond in
which they share 1 pair of electrons. (2 e-)

● ●
C C ● C C
●● ●
● ●
Double Bond – carbon atoms may
share 2 pairs of electrons to form a
double bond.
● ●
●●
C C ●
C ●● C
●
Triple Bond – carbon atoms may share
3 pairs of electrons to form a triple bond.

C C ●●
●C ●● C ●
●●
 Types Of Compounds
Saturated CompoundS – organic compounds in
which carbon atoms are bonded by SINGLE
bonds.
ex. Methane: CH4 H
H C H
H
 Types Of Compounds
Unsaturated Compound – compounds
where carbon atoms have double or
triple bonds.

ex. ethene: C2H4

H H
H C C H
Homologous Series of Hydrocarbons

•Organic compounds can be classified

into groups with related structures and
properties.

***As size of molecule increases the

boiling and freezing points increase.
Hydrocarbons are organic compounds that
consist of only Carbon and Hydrogen atoms.

H H H
H C H H C C H

H H H
IUPAC Nomenclature of branched alkanes
• suffix -ane specifies an alkane
• prefix tells the number of carbon atoms

Prefix Carbons Prefix Carb on s

meth- 1 undec- 11
eth - 2 dod ec- 12
prop- 3 tridec- 13
but- 4 tetradec- 14
pent- 5 pentadec- 15
hex- 6 hexadec- 16
hept- 7 heptadec- 17
oct- 8 octad ec- 18
non - 9 non adec- 19
dec- 10 eicos - 20
Naming Organic Compounds

• Organic compounds are named according to the

IUPAC (international union of pure & applied
chemistry) system of nomenclature.

Alkanes – end in ane

Alkenes – end in ene
Alkynes – end in yne
 single
●Saturated hydrocarbons
Alkanes = CnH2n+2

• A saturated hydrocarbon contains 5

carbons. What is the formula?
C5H2(5)+2 = C5H12
•A saturated hydrocarbon contains 20
carbons. What is the formula?
C20H2(20)+2 = C20H42

Saturated = Single
Alkanes

• CH4 = methane
• C2H6 = ethane
• C3H8 = propane
• C4H10 = butane
• C5H12 = pentane
The smaller the compound the Lower Boiling
point and Melting point is (less bonds to break)

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Alkenes – CnH2n
series of unsaturated hydrocarbons having
one double bond (C=C)

•Also called ethylene series

(IUPAC name is ethene)
•General formula CnH2n
Alkenes

•C2H4 = Ethene
•C3H6 = Propene
•C4H8 = Butene
•C5H10 = Pentene
•To find the number of
hydrogens, double the
number of carbons.
 1-Butene

This is 1-butene, because the double

bond is between the 1st and 2nd carbon
from the end.

ISOMERS: Molecules have the same

molecular formula, but have different
structural formulas.
Pentene

This is 1-pentene. The double bond is

on the first carbon from the end.

This is not another isomer of pentene.

This is also 2-pentene, just that the
double bond is closer to the right end.
Alkynes –
a series of unsaturated hydrocarbons
that contain 1 triple bond.
•Also called the acetylene series

General formula CnH2n-2

C C
Alkynes

• C2H2 = Ethyne
• C3H4 = Propyne
• C4H6 = Butyne
• C5H8 = Pentyne
Alkyl Groups – have one less hydrogen
than the corresponding alkane.

•CH3 is methyl – one less H than

methane, CH4 H
H C H

H
Draw methyl
C2H5 is ethyl – one less H than ethane C2H6

Condensed
Formula:
CH2CH3

Ethane
C3H7 is propyl – one less H than propane C3H8

propane
 Aromatic HC- those which contain one or more benzene
rings
Benzene – a series of cyclic unsaturated hydrocarbons.

General formula CnH2n-6

Benzene – C6H6 the simplest in the family
H

C
H
C C H

H C C H
C
H
Naming Straight Chain Alkanes

• Count the number of carbons

• Get the root word w/c corresponds to the no.
of carbons
• Add the suffix –ane
Formula Condensed Formula Name

CH4 CH4 Methane

C2H6 CH3CH3 Ethane

C3H8 CH3CH2CH3 Propane

C4H10 CH3CH2CH2CH3 or CH3(CH2)2CH3 Butane

C5H12 CH3CH2CH2CH2CH3 or CH3(CH2)3CH3 Pentane
C6H14 CH3CH2CH2CH2CH2CH3 or CH3(CH2)4CH3 Hexane
C7H16 CH3CH2CH2CH2CH2CH2CH3or Heptane
CH3(CH2)5CH3
C8H18 CH3(CH2)6CH3 Octane
C9H20 CH3(CH2)7CH3 Nonane
C10H22 CH3(CH2)8CH3 Decane
Naming Branched Alkanes

• Identify the parent chain

• Parent chain – the longest continuous chain of
carbon atoms
• Assign a number to all the carbon atoms from
the nearest branch
• Name the branch (no. first to where it is
attached, root word + the suffix –yl)
• Name the parent chain
Sometimes the hydrocarbon chains are not straight
and sometimes they have other elements attached to
them. Here is how they are named:

CH3 - CH2 - CH2 – CH – CH – CH - CH3

CH2 CH3 CH3
CH3
7 6 5 4 3 2 1
CH3 - CH2 - CH2 – CH – CH – CH - CH3
CH2 CH3 CH3
CH3
Step 1: Find the longest continuous chain
of carbons.
All bonds in the chain of carbons
are single bonds so ending is…ane.
There are 7 continuous carbons, so the
parent chain is heptane.
7 6 5 4 3 2 1
CH3 - CH2 - CH2 – CH – CH – CH - CH3
4 5 6 7
1 2 3
CH2 CH3 CH3
CH3
•Step 2: Number the carbons in the main
sequence starting with the end that will give
the attached groups the smallest #.

This chain is numbered from right to left

because there is a substituent closest to
the right.
 7 6 5 4 3 2 1
CH3 - CH2 - CH2 – CH – CH – CH - CH3
CH2 CH3 CH3
CH3
• Step 3 : Add
numbers to the names of the groups to identify
their positions on the chain.

- these numbers become prefixes to the parent

chain. yl
ethane
In this ex. the positions are:
C2H6
5
2 - methyl, 3 - methyl, 4- ethyl
7 6 5 4 3 2 1
CH3 - CH2 - CH2 – CH – CH – CH - CH3
CH2 CH3 CH3
CH3
• Step 4: Use prefixes to indicate the appearance of a
group more than once in the structure.

Di = twice
Tri = three times
Tetra = four times
Penta = five times
7 6 5 4 3 2 1
CH3 - CH2 - CH2 – CH – CH – CH - CH3
CH2 CH3 CH3
CH3
•This chain has 2 methyl groups so dimethyl
is used.
Step 5: List the alkyl groups in alphabetical
order.
In this ex. dimethyl is listed before the ethyl.
7 6 5 4 3 2 1
CH3 - CH2 - CH2 – CH – CH – CH - CH3
CH2 CH3 CH3
CH3

Step 6: Use punctuation

- use commas to separate numbers
-hyphens to separate numbers with
words.
7 6 5 4 3 2 1
CH3 - CH2 - CH2 – CH – CH – CH - CH3
CH2 CH3 CH3
CH3
• The name of this compound is:

4-ethyl-2,3-dimethyl heptane
 CH3 CH3
CH3 - CH2 – CH – CH2 – CH - CH3
6 5 4 3 2 1

Step 1: 6 carbons = hex

All single bonds = ends in ane
So parent chain is hexane

Step 2: start numbering from right to left

Step 3: 2 -methyl and 4 -methyl
 CH3 CH3
CH3 - CH2 – CH – CH2 – CH - CH3
6 5 4 3 2 1

2,4 dimethyl hexane

When naming with a double/triple bond-
start # carbons closest to the
DOUBLE/TRIPLE bond.
CH3 CH3

C C C C C
1 2 3 4 5

3,4 dimethyl, 2-pentene

•3-ethylhexane

C C C C C C
CH2
CH3
You can place H’s all around or just leave as is.

H C H
yl
H C H ethane
C 2H 6
H 5
•2,2,4-trimethylpentane

CH3
C C C C C

CH3 CH3
• 2,3,4,5,6,7-hexamethyl-octane
• 4-ethyl-octane
• 2-methyl-nonane
• 2-ethyl-2methyl-butane
• 3-ethyl-pentane
• 2-ethyl-2-methyl-heptane
DRAW THE S.F

• 4-ethyloctane
• 2-methylnonane
• 3,3-dimethylpentane
• 3-ethyl-2methylheptane
• 3-ethyl-2,2-dimethyl-hexane
Naming of simple cycloalkanes:

cyclopropane

cyclobutane

cyclopentane

cyclohexane

cycloheptane

cyclooctane
 Naming Alkenes
Look and study the names of the following alkenes
Alkene IUPAC Common

H2C=CH2 ethene ethylene

H2C=CH─CH3 propene propylene

cyclohexene

CH2=CH─CH2─CH3 1-butene
CH3─CH=CH─CH3 2-butene
How is the naming of alkenes done? Talk over with
your group members 73
Naming Alkynes
Now, let’s look at the case of alkynes. Naming is done in a
fashion similar to that of alkenes.

Alkyne IUPAC Common

HC≡CH ethyne acetylene

HC≡C─CH3 propyne
Br
4-Bromo-2-pentyne
H3C CH C C CH3
5 4 3 2 1

cycloheptyne
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Naming Alkenes and Alkynes with Substituents

Now what if the alkene or alkyne has a substituent? Here is an

example. Write the IUPAC name for
CH3
│
CH3─CH─CH=CH─CH3
STEP 1 Name the longest carbon chain pentene

STEP 2 Number the chain from the double bond

CH3
H
CH 3 C
H3C 4 C 2 CH3 2-pentene
5 H 1

STEP 3 Give the location of each substituent: 4-methyl- 2-pentene

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 CH3
│
HC≡C─CH─CH3

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•4-methyl-2-heptene
•3-ethyl-4,4,5-trimethylhexyne
•5,6-dimethyl-2-octyne
•4-ethyl-4-methyl-2-heptyne
Learning Check

Write the IUPAC name for each of the following:

Solution
1. CH2=CH─CH2─CH3
1) ______________
2. CH3─CH=CH─CH3
2) ______________
CH3
| 3) ______________
3. CH3─CH=C─CH3

4) ______________
4. CH3─CC─CH3
86
Learning Check

Write the structural formula for each of the

following:
Solution
A. 2-pentyne a) _______________

B. 3-methyl-2-pentene b) ________________

87
Cis and Trans Isomers
In an alkene, cis and trans isomers are possible
because the double bond
• Is rigid.
• Cannot rotate.
• Has groups attached to the carbons of the double bond that
are fixed relative to each other.
CH3 CH3 CH3

CH = CH CH = CH
cis trans CH3

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Cis-Trans Isomers
Cis-trans isomers occur when
different groups are attached to
the double bond.
• In a cis isomer, groups are attached on
the same side of the double bond.
• In the trans isomer, the groups are
attached on opposite sides.

Copyright © 2007 by Pearson Education, Inc.

Publishing as Benjamin Cummings
89
 Other Organic Compounds
• Functional Groups – specific groupings of atoms
that give characteristic properties to organic
compounds.

halides F (fluoro-)
Cl (chloro-)
Br (bromo-)
I (iodo-)
What group do these belong to?
Halogens
•Alcohols -OH hydroxyl
•Organic acids -COOH carboxyl

•Aldehydes carbonyl
O -CHO
•Ketones
-C-
•Ethers
-O-
O
•Esters
-C-O
•Amines -NH2-
O
•Amides
-C-NH2
 Halides
Cmpds that are formed
when any halogen
(F,Cl,Br,I) replaces an H
atom in an alkane.

The functional group

is the halide
(F,Cl,Br,I)
Halides
• They are named by citing the location of the
halogen attached to the chain
Drop the “ine” and add “o”
F

2- fluoropropane
 Alcohols

• Are organic cmpds in which one or more of the hydrogens

is replaced with an – OH group.

- OH group is called the hydroxyl group

Monohydroxyl Alcohols
-have one –OH group
H
R C OH

H
Shortcut way to represent a primary alcohol
R-OH
R stands for REST of the molecule
 IUPAC naming of alcohols
• Replace the final “e” with “-ol”
● methane methanol CH3OH
● ethane ethanol C2H5OH
● propane propanol C3H7OH
● butane butanol C4H9OH
● pentane pentanol C5H11OH
Ex. 2-propanol

H OH H
H C C C H
H H H

1 2 3
 Organic acids – have the functional
group
-COOH
• R-COOH

O
Carboxyl
R C
group OH
 IUPAC naming of Organic Acids

 Replace the final “e” with “-oic ”acid

H

Methanoic acid - HCOOH H C H

H

O
R C
OH
Aldehydes- contain the functional
group -CHO
O
R C
H
R-CHO
 IUPAC naming of Aldehydes
•Replace the final “e” the the ending “al”
First member of the aldehyde family is methanal
-its common name is formaldehyde
Used to
2 O preserve
H C 3 biological
1 samples
4 H
 • Alcohols can be oxidized to aldehydes

H O
R C OH + Oxidizing R C + H20
agent H
H
methanol methanal water
Draw ethanal

H
O
H C C
H
H
 Ketones – contain the functional group
-CO-
 Replace the final “e” with “-one”.

• The simplest member of the

ketone family is propanone.
• IUPAC name is propanone but its common
name is acetone, it is an important industrial
solvent.
R R

H O H

H C C C H
H H
 Ethers
• when two primary alcohols are treated with a dehydrating
agent, water is removed and the 2 alcohols are joined
together by an oxygen “bridge”.

R-OH + R-OH R-O-R + H20

Primary Primary ether

alcohol alcohol

H2O
Diethyl ether- used as a general
anesthetic
ethyl ethyl

H H H H

H C C O C C H
H H Oxygen bridge H H

Condensed formula
CH3 CH2 -O- CH2 CH3
Dimethyl ether-

methyl methyl

H H

H C O C H
H Oxygen bridge H

Condensed formula
CH3 -O- CH3
 Name These:
Condensed
formula CH3-O- CH2 CH3
Methyl ethyl ether

CH3CH2-O- CH2CH2CH3
Ethyl propyl ether
 Esters – are organic cmpds with the
general formula R-CO-O-R
O
They are formed in a rxn
between an organic acid C O
and an alcohol.
Draw this:

Esters have strong fragrant aromas and are

what make pineapples, bananas,
wintergreen & oranges so YummY!
IUPAC naming of Esters:
H H O H H
H C C C O C C H
H H H H

1. Look at chain after the –C-O- write its prefix

Ex.(meth,eth, etc.) and add –yl to the end of prefix

In this ex. : eth + yl = ethyl

 H H O H H
H C C C O C C H
H H H H
Condensed formula
CH3 CH2 COO CH2CH3
2. Give the name of the carbon chain that includes the
C=O, leave off the last letter and add –oate.
Propane - 3 C’s and single bonds
propane + oate = propanoate
Ethyl propanoate
Ex.) Draw ethyl pentanoate

H H H H O H H
H C C C C C O C C H
H H H H H H

Now you’ve got it!

 Amines – contain the functional group
–NH2-
• It is a derivative of ammonia – NH3
• IUPAC naming of amines –
- replace the final –e with “-amine”

H Draw:

H C NH2 C C NH2

H
ethanamine
methanamine
 Amides – contain the functional group:
O

C NH
Found at the end of a carbon chain
• IUPAC naming of amides:
-drop the final –e and add “amide”

H H O
H C C C NH2 propanamide
H H
 Amide

butanamide

Synthetic Polyamides: nylon, kevlar

Natural Polyamide: silk!
 Organic Reactions
•Substitution – replacement of one kind of
atom or group with another atom or group

• If this rxn occurs between an alkane

and a halogen, it is called
halogenation.

*only happens with alkanes –

single bonds!!!!
Substitution

+ Br2 Br + HBr

Hydrogen
Butane + bromine Bromobutane +
bromide

C4H10 + Br2  C4H9Br + HBr

The second Br can then substitute for another H.

For Ex: Find the products of

C3H8 + F2  C3H7F + HF
 Addition –adding one or more groups at
a double or triple bond.
•Double bond is broken…becomes a single bond.

*only happens with alkenes &

alkynes – double/triple bonds!!!!
 Addition
• Alkene + Halogen  Alkyl Halide
• The double bond is broken, and the halogen adds
at either side of where the double bond was.
saturated

unsaturated
 Fermentation
-Molecules are broken down
- enzymes act as catalysts
-Anaerobic respiration

glucose ethanol + Carbon

dioxide
 Esterification
• Organic Acid + Alcohol  Ester + Water
-COOH -OH -COO -H2O

-These are slow reversible reactions

-similar to neutralization rxn in inorganic

Acid + base = salt + water

 Saponification – is the hydrolysis of fats
by bases.
•The breaking of an ester to produce an organic acid plus
analcohol
(glycerol ester)
.
(soap) (alcohol)

Fat + water = organic acid + glycerol

What is this the reverse process of?

Esterification
Organic Acid + Alcohol  Ester + Water
Saponification - hydrolysis of an ester in
presence of a hot base (alkali)
Glycerol ester + 3 NaOH  soap + glycerol

Fat base alcohol soap

 Polymers- are composed of many
repeating units of monomers
• Natural polymers
-starch – long chains of sugars
-proteins – long chains of amino acids
-cellulose – made of repeating units of sugar

starch cellulose
 Polymers
• Synthetic (man made) polymers:
- nylon, rayon - polyester

- polyethylene - silicone
 Polymerization- formation of polymers
from monomers
• Formation of larger molecules from smaller ones.

2 Methods :

1. Condensation polymerization: bonding

of monomers by dehydration synthesis
 Monomers have at least two functional groups
 -OH on ends
 Condensation polymerization
Ex.) H 2O
H H H H
HO C C
HO
+ HO C C
HO
H H Leaves an H H
monomer oxygen bridge monomer

H H H H
+
O HO
HO C C C C H 2O
H H H H
polymer
Addition Polymerization -

C C + C C + C C
monomer
monomer monomer
ethylene
ethylene
ethylene
C C C C C C

polymer

polyethylene
 Finding missing reactants & products in
organic rxns
• In balanced rxns the number of atoms on the left must equal the number of atoms on the
right.

Ex.) C2H6 + Cl2 C2H5Cl +

Left side Right side missing

C= 2 C= 2 C= 0
H= 6 H= 5 H= 1
Cl = 2 Cl = 1 Cl = 1
Missing product must be HCl
This is a substitution rxn because hydrogen atom
of ethane is replaced by chlorine.
• Try this one:
Ex.) C2H4 + Br2 C2H4 Br2
This is a addition rxn

 What process makes…

saponification
combustion
fermentation

addition
polymerization
Condensation
polymerization