Structure of Carbon

Compounds

1 New Way Chemistry for Hong Kong A-Level Book 3A

INTRODUCTION TO ORGANIC CHEMISTRY
 Initially the word organic was given to molecules found in living things and
organic chemistry referred to the chemistry of compounds from living
organisms.
 Friedrich Wohler discovered in 1828 that urea can be produced from
inorganic starting materials and proofed that biological substance could be
synthesized in the laboratory without biological starting materials.
With time, it was found that the only distinguishing characteristic of organic
compounds is that all contain the element carbon.
 Then Organic Chemistry came to mean the study of carbon-containing
compounds.
Other elements which is commonly presented in organic substances are H,
O, halogens (Cl, Br, F), N and S.

2 New Way Chemistry for Hong Kong A-Level Book 3A

 Organic chemistry is important because the vital biological molecules in
living systems are largely organic compounds.

 Animals, plants & other form of life consists of organic compounds such
as nucleic acids, proteins, fats, carbohydrates, enzymes, vitamins &
hormones.

 Not all organic compounds are derived from living organisms; dyes,
polymers, plastics and pesticides are prepared in the laboratory.

 Organic compounds are all around us and thus organic chemistry is a

important yet a fascinating study.

 Compounds that are considered organic must contain carbon bound to

hydrogen and possibly other elements. By this definition, carbon
dioxide, carbon tetrachloride, calcium carbide and sodium carbonate
are all inorganic (Carbon oxides, carbides and carbonates are exception for
carbon containing compounds as organic)

3
3 New Way Chemistry for Hong Kong A-Level Book 3A
 INORGANIC & ORGANIC
Inorganic – chemistry of element other than carbon.
 Propane, C3H8, is an
organic compound
used as a fuel.

 NaCl, salt, is an
inorganic compound
composed of Na+ and
Cl- ions.

Why is propane organic,

but NaCl is not?
4 New Way Chemistry for Hong Kong A-Level Book 3A
 INORGANIC & ORGANIC
Organic Compound?
Yes or No

Na2CO3 No

C2H6 Yes!

C4H6Br2F2 Yes!
SiC, CaC2 No
5 New Way Chemistry for Hong Kong A-Level Book 3A
ORGANIC COMPOUNDS: SOURCES FROM LIVING THINGS

Living Carbohydrates /
things Peptides /Collagen /
Proteins / Fats /
Vitamins / Antibiotics

A variety of
organic products
obtained from
living things

6 New Way Chemistry for Hong Kong A-Level Book 3A

 ORGANIC COMPOUNDS: SOURCES FROM NON-
LIVING THINGS

Fractional distillation / Alkanes /

destructive distillation Alkenes /
Crude oil
Alkynes /
or coal
Aromatic
hydrocarbons

A variety of useful products derived

7 from crude oil and
New Way coal
Chemistry for Hong Kong A-Level Book 3A
 The Unique Nature of Carbon

“The bonds that carbon atoms form give rise to unique

properties of organic compounds”

8
8 New Way Chemistry for Hong Kong A-Level Book 3A
 CARBON ATOM IN PERIODIC TABLE

9 New Way Chemistry for Hong Kong A-Level Book 3A

 1. Ability to form four strong covalent bonds

 Carbon atoms form strong covalent

bonds, in which they share electrons
with one or more other atoms.
 Electronic configuration of carbon
(ground state) : 1s22s22p2

Carbon (ground state)

10 New Way Chemistry for Hong Kong A-Level Book 3A
 2. Ability to Catenate
 Carbon atoms link together to form
chains of varying length, branched
chains and rings of different sizes
Inorganic compound will become unstable after with 12

or more atoms.

 Catenation:
 Ability of atoms in forming stable
bonds with itself, hence joining up into
11 chainsNewor
Wayrings
Chemistry for Hong Kong A-Level Book 3A
 3. Ability to Form Multiple
Bonds
Single bond Double bond Triple bond

* X = halogens

12 New Way Chemistry for Hong Kong A-Level Book 3A

 Principle of
Atomic Structure

13 New Way Chemistry for Hong Kong A-Level Book 3A

 STRUCTURE OF ATOMS

Atomic number: the total

number of protons in the
nucleus of each atom of an
element.

Mass number: the sum of

all the protons & neutrons
present in the nucleus of
an atom.
14 New Way Chemistry for Hong Kong A-Level Book 3A
 STRUCTURE OF ATOMS
Electrons that are bound to nuclei are found in orbitals.

A region around the nucleus where there is a high

probability of finding an electron.
 Electrons can occupy 4 types of orbitals
s, p, d, f

15
p orbitals
New Way Chemistry for Hong Kong A-Level Book 3A
 STRUCTURE OF ATOMS
 Atomic orbitals are grouped into different “shells” at
different distances from nucleus.
 Each shell is identified by a principle quantum
number n
 The first shell (n=1) can hold 2 electrons & second
shell (n=2) can hold 8.
Principle shell n No. of sub-shell symbol
1st 1 1 1s
2nd 2 2 2s, 2p
3rd 3 3 3s, 3p, 3d

The number of orbitals depends on the type of sub-shell.

sub-shell No. of orbitals symbol
s 1 s
p 3 px, py, pz
16 New Way Chemistry for Hong Kong A-Level Book 3A
 ELECTRONIC CONFIGURATION
3 rules in determining the electronic
configuration of an element

17 New Way Chemistry for Hong Kong A-Level Book 3A

 ELECTRONIC
CONFIGURATION The Aufbau Principle
The electrons in their ground states occupy orbitals
in order of their energy level.
The lowest energy orbital is always filled first.

18
1s, 2s, 2p, 3s, 3p, 4s, 3d, 4p, 5s, 4d, 5p, 6s, 4f, 5d, 6p, 7s,
New Way Chemistry for Hong Kong A-Level Book 3A
 ELECTRONIC
CONFIGURATION The Pauli Exclusion

 An orbital can accommodate a maximum of 2 electrons

& then only if they have opposite spins (↑ and ↓).
 The total number of electrons in an orbital or set of orbitals:

19 New Way Chemistry for Hong Kong A-Level Book 3A

 ELECTRONIC
CONFIGURATION The Hund’s Rule
 The orbitals of a sub-shell must be occupied singly by
electrons with parallel spins before they can be
occupied in pairs.

For example, the two electrons in a p orbital is

and not .

20 New Way Chemistry for Hong Kong A-Level Book 3A

 ELECTRONIC CONFIGURATION

21 New Way Chemistry for Hong Kong A-Level Book 3A

 Structure &
Bonding in Carbon
Atoms

22 New Way Chemistry for Hong Kong A-Level Book 3A

 Covalent Bond & Lewis Structure

23
23 New Way Chemistry for Hong Kong A-Level Book 3A
 Bonding in Carbon atoms

Electron Configuration

4 valens electron
4 covalent bonds

24
24 New Way Chemistry for Hong Kong A-Level Book 3A
 Resonance
A way of describing delocalized electron within certain molecules or
polyatomic ions where the bonding cannot be expressed by one single
Lewis Structure

CO3-2

O O O O O O
N N N

O O - O
25
NO3
25 New Way Chemistry for Hong Kong A-Level Book 3A
 Resonance

26
26 New Way Chemistry for Hong Kong A-Level Book 3A
 Resonance

27
27 New Way Chemistry for Hong Kong A-Level Book 3A
 COVALENT BONDING
Covalent Bond

Non-polar Polar
1. 2 nonmetal atoms of the 1. Two different nonmetal
same kind bind to each atoms are bonded
other.
2. Electrons are unequally
2. Electrons are shared shared between the 2
equally between the 2 atoms.
atoms.
3. Example: HCl molecule
3. Example: the bond in H2
and C-C in ethane H Cl

28 New Way Chemistry for Hong Kong A-Level Book 3A

 Nonpolar Covalent Bonds: Electrons are
shared equally

29 New Way Chemistry for Hong Kong A-Level Book 3A

 Polar Covalent Bonds: Unevenly
matched, but willing to share.

30
30 New Way Chemistry for Hong Kong A-Level Book 3A
 ELECTRONEGATIVITY
• The tendency of an atom to attract electrons or
electron density towards itself.

• Used to predict whether a bond will be polar

or non-polar.

• Elements with higher electronegativities

(nitrogen, oxygen, and the halogens) will have
more attraction for bonding electrons.

• The electronegativity of carbon and hydrogen are

similar, C—H bonds are considered to be
nonpolar.
31 31 New Way Chemistry for Hong Kong A-Level Book 3A
 POLARITY OF MOLECULES

 Polarity results from the uneven partial

charge distribution between various atoms in
a compound.
 Atoms, such as nitrogen, oxygen, and
halogens, that are more electronegative have
a tendency to have partial negative charges.
 Atoms, such as carbon and hydrogen,
have a tendency to be more neutral or have
partial positive charges.
32
32 New Way Chemistry for Hong Kong A-Level Book 3A
 POLARITY OF MOLECULES

Polar : As a result of an unsymmetrical

distribution of electrons, the bond or molecule
contains a positive and a negative pole (dipole).

Nonpolar : A symmetrical distribution of

electrons leads to a bond or molecule with
no positive or negatives pole.

33 New Way Chemistry for Hong Kong A-Level Book 3A

 POLARITY OF MOLECULES: DIPOLE MOMENT

Dipole Moment (µ) –

The dipole moment is a measure of the polarity of the molecule.
The product of magnitude of charge & distance of separation between the
charges

34 New Way Chemistry for Hong Kong A-Level Book 3A

 INTERMOLECULAR FORCES

 Forces or attraction that exists between the

molecules.
 Classification depends on structure:
1. London dispersions forces
2. Dipole–dipole interactions
3. Hydrogen bonding

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35 New Way Chemistry for Hong Kong A-Level Book 3A
 INTERMOLECULAR LONDON
FORCES DISPERSION FORCES
 Result from the approach of two nonpolar
molecules.
 Arises from temporary dipole moments that are
induced in a molecule by another nearby
molecules.
 A small temporary dipole moment is induced
when one molecule approaches another molecule.
 The electrons in the approaching molecule are
displaced slightly so that an attractive dipole
interaction results.
 These temporary dipoles last only a fraction of
second, & they constantly change
36 New Way Chemistry for Hong Kong A-Level Book 3A
 INTERMOLECULAR LONDON
FORCES DISPERSION FORCES
Effect of Branching on Boiling Point

 The long-chain isomer (n-pentane) has the greatest

surface area and the highest boiling point.
 As the amount of chain branching increases, the
molecule becomes more spherical and its surface area
decreases.
 The most highly branched isomer (neopentane) has the
smallest surface area and the lowest boiling point.
37
37 New Way Chemistry for Hong Kong A-Level Book 3A
 INTERMOLECULAR LONDON
FORCES DISPERSION FORCES
Geckos

Although any single London dispersion forces is weak, a

large number of London dispersion forces creates a strong
force. For example, geckos stick to walls and ceilings by the
London forces interactions of the surfaces with the 500,000
tiny hairs on each foot.
38 New Way Chemistry for Hong Kong A-Level Book 3A
 INTERMOLECULAR DIPOLE-DIPOLE
FORCES INTERACTION
 Most molecules have permanent dipole moment as a
results of their polar bonds.
 Attractive intermolecular forces resulting from the
attraction of the positive & negative ends of the dipole
moments of polar molecules.
 Larger dipoles causes higher boiling points.

dipole dipole
+ -
-
+
H Cl H Cl
Attractive force

39 New Way Chemistry for Hong Kong A-Level Book 3A

 INTERMOLECULAR HYDROGEN
FORCES BONDING
Example:

H
 The oppositely charged

+
poles on the water molecules
attract each other.
Water

H
O
-
 It is the strongest form of
intermolecular attraction.
H
 Hydrogen bonding exists only
between molecules in which
+ O -
hydrogen is bonded to a H
very electronegative atom
(O-H or N-H)

-
O
 Result in abnormally high
H
boiling points.
+
H
40 New Way Chemistry for Hong Kong A-Level Book 3A
 INTERMOLECULAR HYDROGEN
FORCES BONDING
The hydrogen from one molecules is strongly attached to a
lone pair of electrons on the other molecule.
hydrogen hydrogen
H bond H bond
H3C H CH3
O O N N
H CH3 H3C H
H
H H
O N
H3C H CH3

CH3
methanol, H O CH3 mehtylamine, H N
CH3

41
41 New Way Chemistry for Hong Kong A-Level Book 3A
 INTERMOLECULAR HYDROGEN
FORCES BONDING
Hydrogen bonding in Nylon

Nylon is a polymer, a large organic molecule. The long

chains of nylon are held together by hydrogen bonding
interactions, with the N-H of one chain hydrogen bonded to
an O atom in an adjacent chain. This intermolecular forces
strengthen nylon fibers.
42
42 New Way Chemistry for Hong Kong A-Level Book 3A
 INTERMOLECULAR FORCES: SUMMARY

Type of force Relative Exhibited by Example

strength

London dispersion weak usually nonpolar CH3CH2CH2CH2CH3

forces

Dipole-dipole moderate Polar molecules CH3CH2CH2CH2OH

forces CH3CH2Br

Hydrogen bonding strong Molecules with an O-H, CH3CH2CH2CH2OH

N-H or H-F bond CH3CH2NH2

43
43 New Way Chemistry for Hong Kong A-Level Book 3A
 INTERMOLECULAR FORCES: SUMMARY
Rank the following compounds in order of increasing strength of intermolecular
forces:
CH3CH2CH2CH2CH3(pentane), CH3CH2CH2CH2OH(1-butanol), & CH3CH2CH2CHO
(Butanal)
CH3CH2CH2CH2CH3 CH3CH2CH2CH2OH CH3CH2CH2CHO
(pentane) (1-butanol) (Butanal)

Nonpolar molecule polar C-O & O-H bond polar C=O bond

OH for hydrogen bonding

- Pentane: Has only nonpolar C-C & C-H bonds, so its molecules are held
together only by London forces.
- 1-butanol: Polar molecule, so it can have dipole-dipole interactions & London
forces. Because it has an O-H bond, 1-butanol molecules are held together by
intermolecular hydrogen bonding as well.
- Butanal: Has a polar C=O bond, so it exhibits dipole-dipole interactions and
London forces.
44

44 CH3CH2CH2New
CHWay
2CHChemistry
3 forCH 3CH
Hong 2CH
Kong 2CHO
A-Level BookCH
3A 3CH2CH2CH2OH
 HYBRIDIZATION IN ORGANIC MOLECULES

 Hybridization: The combination of two or

more atomic orbitals to form the same number of
hybrid orbitals, each having the same shape &
energy.
3 type of hybridization present in organic
compounds that are sp3 , sp2 and sp:
s orbitals p orbitals Hybrid Bond
orbitals
1 3 sp3 Single bond
1 2 sp2 Double bond
1 1 sp Triple bond

45 New Way Chemistry for Hong Kong A-Level Book 3A

 HYBRIDZATION-sp3
THE STRUCTURE OF METHANE AND ETHANE:
sp3 HYBRIDZATION
Orbital hybridization: A mathematical approach that involves the
combining of individual wave functions for s and p orbitals to obtain wave
functions for new orbitals ⇒ hybrid atomic orbitals

2sp3

46 New Way Chemistry for Hong Kong A-Level Book 3A

 HYBRIDZATION-sp3

47 New Way Chemistry for Hong Kong A-Level Book 3A

 HYBRIDZATION-sp3 (Methane)
Formation of a C–H bond

48 New Way Chemistry for Hong Kong A-Level Book 3A

 HYBRIDZATION-sp3 (Ethane)

Formation of C-C and C–H bond

49 New Way Chemistry for Hong Kong A-Level Book 3A

 HYBRIDZATION-sp2

A process for obtaining sp2-hybridized carbon

atoms
50 New Way Chemistry for Hong Kong A-Level Book 3A
 HYBRIDZATION-sp2 (Ethylene)

51 New Way Chemistry for Hong Kong A-Level Book 3A

 HYBRIDZATION-sp

A process for obtaining sp-hybridized carbon atoms

52 New Way Chemistry for Hong Kong A-Level Book 3A
 HYBRIDZATION-sp
(ACETYLENE)

53 New Way Chemistry for Hong Kong A-Level Book 3A

 THE END

54 New Way Chemistry for Hong Kong A-Level Book 3A