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ORGANIC

CHEMISTRY I
2009

ORGANIC CHEMISTRY I

Gregg Taylor
Office A307, extension 2415
gregg.taylor@durhamcollege.ca

THE COURSE OUTLINE

Download a copy from MyCampus


Really useful to download all of your course
outlines electronically save on a USB drive
Good to have to show prospective employers
and/or other academic institutions should
you choose to take more courses in future
Also good to have to help follow the course
curriculum

ORGANIC CHEMISTRY

Lecture/lab course
Labs really bring the lecture material into
clearer focus you get to see and handle the
actual chemicals that you only see on the
presenter as drawings
Important to attend and participate
Key part of the course labs are worth 30%

ORGANIC CHEMISTRY

This is a participatory subject


Practicing the material and learning it in
steps is the best approach
To assist in this, we will be doing a number
of in-class assignments we will discuss a
topic in class and then try solving some
questions
These in-class assignments are worth 10% of
the course (it is important to participate)

ORGANIC CHEMISTRY

Help sessions can be arranged if you find you


are having difficulty with the material
Please ask for help before the day of the test
I will try to make sure that practice
questions are available for you (as well as
the questions in your textbook which are
quite helpful)

TEXTBOOK

Textbooks are not mandatory (depending on


your financial situation)
However, I highly recommend having a
textbook (and I will assign practice questions
from it)
There are several virtual organic chem
textbooks on the web
There are also several textbooks in the
library

THE WONDERFUL WORLD OF


ORGANIC CHEMISTRY

Over the course of the term, we will look at


a wide variety of types of organic compounds
with respect to:
Terminology
Nomenclature
Physical properties
Preparation
Chemical reactions
Toxicological properties
Lab techniques and methods

WHAT IS ORGANIC CHEMISTRY


ANYWAY?

Way back in the mists of time, any substance


from a living organism was imbued with
magic and mystery
Compounds having an organic origin were
somehow different from other compounds
Even in the 1800s, when chemistry was
studied systematically, this was still the
prevailing belief

THE NATURE OF ORGANIC


CHEMISTRY

Compounds were either from living or nonliving sources


Inorganic compounds came from non-living
sources NaCl, HCl, Cu, Fe, etc
Organic compounds existed in living
organisms and had a vital force

THE NATURE OF ORGANIC


CHEMISTRY

This distinction between organic and


inorganic compounds fell apart when it was
discovered that a simple inorganic
compound, ammonium cyanate, could be
chemically converted to a known organic
compound urea

The magic was gone from the world and a


new era was upon us.

ORGANIC CHEMISTRY

NH4OCN H2NCONH2

Simply heating ammonium cyanate caused


urea to form

Urea was suddenly just a chemical and was


no longer the stuff of magic

ORGANIC CHEMISTRY

We needed a new definition of organic


chemistry
The one common factor with all organic
compounds was that they contained CARBON
Pretty simple definition
Not always strictly abided by we often think
of Na2CO3 as an inorganic salt (although it
does contain C)

ORGANIC CHEMISTRY

If you look at the periodic table, there are an


awful lot of elements besides carbon
Why define an entire scientific study to one
element?

PERIODIC TABLE
IA
1
H
1.008
3
Li
6.941
11
Na
22.99
19
K
39.1
37
Rb
85.47
55
Cs
132.9
87
Fr
(223)

IIA
4
Be
9.012
12
Mg
24.31
20
Ca
40.08
38
Sr
87.62
56
Ba
137.3
88
Ra
226

IIIB
21
Sc
44.96
39
Y
88.91
57
La
138.9
89
Ac
227

IIIA
5

VIIB
25
Mn
54.94
43
Tc
-98
75
Re
186.2

VIIIB
26
27
Fe
Co
55.85 58.93
44
45
Ru
Rh
101.1 102.9
76
77
Os
Ir
190.2 192.2

B
10.81
13
Al
IB
IIB 26.98
28
29
30
31
Ni
Cu
Zn
Ga
58.69 63.55 65.39 69.72
46
47
48
49
Pd
Ag
Cd
In
106.4 107.9 112.4 114.8
78
79
80
81
Pt
Au
Hg
Tl
195.1 197 200.6 204.4

58
59
60
61
Ce
Pr
Nd
Pm
140.1 140.9 144.2 (145)
90
91
92
93
Th
Pa
U
Np
232
231
238
237

62
63
Sm
Eu
150.4 152
94
95
Pu
Am
(244) (243)

64
Gd
157.3
96
Cm
(247)

IVB
22
Ti
47.88
40
Zr
91.22
72
Hf
178.5

VB
23
V
50.94
41
Nb
92.91
73
Ta
180.9

VIB
24
Cr
52
42
Mo
95.94
74
W
183.9

65
Tb
158.9
97
Bk
(247)

66
Dy
162.5
98
Cf
(251)

67
Ho
164.9
99
Es
(252)

IVA
6
C
12.01
14
Si
28.09
32
Ge
72.61
50
Sn
118.7
82
Pb
207.2

68
Er
167.3
100
Fm
(257)

15

VA
7
N
14.01
15
P
30.97
33
As
74.92
51
Sb
121.8
83
Bi
209

VIA
8
O
15.99
16
S
32.07
34
Se
78.96
52
Te
127.6

VIIA
9
F
19
17
Cl
35.45
35
Br
79.9
53
I
126.9
85
Po
At
(209) (210)

69
70
71
Tm
Yb
Lu
168.9 173
175
101
102
103
Md
No
Lr
(258) (259) (260)

VIIIA
2
He
4.003
10
Ne
20.18
18
Ar
39.94
36
Kr
83.8
54
Xe
131.3
86
Rn
(222)

ORGANIC CHEMISTRY

Organic chemicals are everywhere


There are over 16 million fully characterized
organic compounds and this number is
growing every year

ORGANIC CHEMISTRY

Originally, the study of organic chemistry was


restricted to those compounds which occurred
naturally
When the 1900s hit, it was discovered that we
could use a number of reagents to synthesize
new chemicals or to modify existing
compounds
This gave rise to a phenomenal surge in the
number of new chemicals used in the chemical
industry (as dyes, lubricants, fuels, etc), in the
pharmaceutical industry and in the food
industry.

ORGANIC CHEMISTRY

Now organic chemicals are everywhere we


look

IN CLOTHING

Cotton
Wool
Silk
Synthetic fabrics (polypropylene, polyesters,
rayon, etc)
Dyes
Fabric treatments wrinkle resistant, water
resistant, stain resistant, flame retardant
treatments

IN FOODS

Carbohydrates
Proteins
Amino acids
Vitamins
Preservative
Food colours
Natural and artificial flavours
Texture enhancing chemicals
Artificial sweeteners
Fat substitutes
Etc, etc

BIOCHEMISTRY

Proteins
Amino acids
Enzymes
DNA
RNA
Purines, pyrimidines
Carbohydrates
(some still consider these to be a special,
almost still magical, type of organic chemicals)

IN ENERGY

Natural gas
Petroleum
Diesel
Ethanol
Fuel additives eg MTBE

IN MEDICINE

Almost all pharmaceuticals are organic


chemicals

INDUSTRIAL CHEMICALS

Lubricants
Adhesives
Paints, pigments
Plastics
Chemical additives
Fine chemicals
Nanotechnology (carbon nanotubes etc)

ENVIRONMENTAL

Of course, most of these wonderful organic


chemicals end up in the environment (not in a
beneficial way)
PCBs
VOCs
POPs
Insecticides
Herbicides
Endocrine disruptors
Organometallics
Etc, etc, ad nauseum

WHY ARE THERE SO MANY


COMPOUNDS OF CARBON?

THE COMPOUNDS OF CARBON

Carbon likes to form covalent bonds with


other elements
It especially likes to form bonds to other
carbon atoms as well as other non-metals
(and in some cases, metals)
Leads to an enormous number of possible
structures
Many of these compounds are quite
chemically and thermally stable

THE COMPOUNDS OF CARBON

It is relatively simple to convert one type of


carbon compound into another type
This is the field of synthetic organic
chemistry

BONDING TO CARBON

Assume you already know all about bonding


in chemistry
Ionic vs covalent bonds
Electron transfer vs electron sharing
Polar covalent bonds
Coordinate covalent bonds

BONDING TO CARBON

Carbon chemistry uses covalent bonds


(although many organic compounds also
contain ionic bonds)
There is a continuum from ionic to polar
covalent to pure covalent bonding (from
non-sharing to unequal sharing to
sharing equally)

POLAR COVALENT BONDS

Polar covalent bonds are particularly


important in organic chemistry
The properties and chemical reactivity of
different compounds depends on the
presence (or absence) of these types of
bonds

PURE COVALENT BONDS

Pure covalent bonds represent equal sharing


of electrons
A pure covalent bond often forms when
attaching two atoms of the same type
H-H
F-F
Cl-Cl
C-C

COVALENT BONDS

C-C and C-H bonds are fairly equal bonds in


many compounds

POLAR COVALENT BONDS

Unequal sharing of electrons between the


atoms comprising the chemical bond is
referred to as a polar covalent bond

One atom in the bond tends to attract the


electron cloud more than the other
Often represent by partial positive and
negative charges within the bond

POLAR COVALENT BONDS

C-H bonds are pretty close to being pure


covalent bonds
The electronegativities of H and C are pretty
similar
In some reactions we can exaggerate the
differences between these atoms but for
the most part they are fairly stable bonds

POLAR COVALENT BONDS

If we look at some inorganic examples to


start:

H-Cl represents a polar covalent bond

The electronegativity of Cl is >> that of H


The electrons are unevenly distributed in this
bond

POLAR COVALENT BONDS

We can represent H-Cl as having a partial


positive charge on hydrogen and a partial
negative charge on Cl

When we place HCl molecules in water, they


ionize to H+ and Cl- ions
(in fact hydrochloric acid is just an aqueous
solution of HCl gas - about 37% by weight)

POLAR COVALENT BONDS

In the world of organic chemistry:

C-O is a polar covalent bond


C-Cl
O-H

In the above, which atom in each bond is


more electronegative?

POLAR COVALENT BONDS

How do we represent which atom is each


bond is more negative or more positive?

We can use partial positive and partial


negative symbols to represent the charge
distribution within the bond

POLAR COVALENT BONDS

Many textbooks go one step better


They represent the charge distribution in
terms of an electrostatic potential map
This looks like a topographical map which
plots out the distortion of the electron cloud
which comprises the bond
Colours are added to show you where the
electron density is located which part is
negative and which is positive

POLAR
AND NONPOLAR MOLECULES

ammonia and formaldehyde are polar molecules


acetylene is a nonpolar molecule

Insert elpot of
ammonia
(page 19)

Insert elpot of
acetylene
(page 20)

N
H

Insert elpot of
formaldehyde
(page 20)

H +
Ammonia
(polar)

C
H + H

H C C H

Formaldehyde
(polar)

Acetylene
(nonpolar)
50

LEWIS DOT DIAGRAMS

REPRESENTING ORGANIC
MOLECULES

Drawing structures of organic compounds: