CHAPTER ONE

REPRESENTATIVE CARBON
COMPOUNDS I
J
Organic Chemistry is most broadly defined as the
chemistry of the compounds of carbon.

An organic compound is best defined as a compound

containing carbon.

Approximately 95% of known compounds are classified

as organic compounds.

The element whose atoms have a unique ability to bond to

each other and to other kinds of atoms is carbon.
( Not Real Overly)
 If Sigma is broken →
Compound is broken since it is difficult to rebuild it

C C C C C C

Single bond Double bond Triple bond

  
 
=

first is Signa

Bond Order (B.O.)

1 2 3
As the Bond Order (B.O.)

As the Bond Length (B.L.)

As the Bond Strength (B.S.)

As the E to break the bond

 FORMAL CHARGES OF
CARBON, NITROGEN AND
O XYGEN ATOMS
^

Most Important
Element
 Notes All Organic Compounds have atleast / Carbon atom .

Formal Charge Carbon Nitrogen Oxygen

Group N°44
Group N 's
"

Group N
"
6

Having None -0 -1 C N O
formal charge
interactions
causes
with other Compounds
N

1 bond makes
N
more
C O
•

it + Ve 7 less bond 0
# final
,

makes it -
ve .
M

C N O
4 Bonds 3 Bonds 2 Bonds

C N

+1 C N O

N O

N O

N
Formal Charge Oxygen Sulfur

-1 O S

O O S S
0

+1 O O O S S S

could the b- orbital I be

0 •
Sulfur use more
S S
than oetate .

•
Although Oxygen & Sulfur are
both in the 6ᵗʰ
group ,
Sulfur has more
ways
to have 0 formal S
charge because sulfur is bigger .

S
 Bond -1 lone Pair -1
O
formulas Group "
W -
Amount

a. H2C N N b. H C O N O c. H3C S CH3

3

Formal Charge (F.C.) = Group number - # of V e’s assigned to the atom (# of e’s on the atom) in the structure.
 Alkanes CnH2n+2
n = 1, 2, 3....etc

If n = 4 C4H10
H could be caleb protons
H H H H
1 2 3 4 1 2 3 4
H C C C C H CH3CH2CH2CH3
H H H H
3
Condensed
1
Dash 2 4
Formula
Formula
Bond-Line
Formula
-
Calculating hybridization is by counting the
Sigma bonds available .

In ALKANES, all carbon atoms should have single bonds & sp3 Hybridization
 Alkenes CnH2n -
You need
from n=2
to start
because
H need to be far
n = 2, 3....etc from other H

If n = 2 C2H4

H H
C Should
C H2CCH2
H have pi bond
-

sp2
Because 3
Sigma bonds
 Alkynes CnH2n-2
n = 2, 3....etc

If n = 2 C2H2

Triple Bond
H C C H HCCH
2
pi bonds
-

sp
Because 2
bonds
Sigma
THE FIRST TEN CONTINUOUS
CHAIN ALKANES
 "

"

"

www.erb Name
Methane
Condesed Molecular Formula
CH4
l

Ethane CH3CH3
CnH2n+2
n = 1, 2, 3....etc
Propane CH3CH2CH3

Butane CH3CH2CH2CH3
Abd CH
, everytime you increase

Pentane CH3CH2CH2CH2CH3

Hexane CH3CH2CH2CH2CH2CH3

Heptane CH3CH2CH2CH2CH2CH2CH3

Octane CH3CH2CH2CH2CH2CH2CH2CH3

Nonane CH3CH2CH2CH2CH2CH2CH2CH2CH3

Decane CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3
FUNCTIONAL GROUPS IN
ORGANIC CHEMISTRY
Functional Group Name Functional Group Name
R represents n=7 -10 Carbon Atoms
Alkane R H Alcohol R OH
1 Bond

Alkene C C H C C
2Doris C C OH C C OH C C OH
Alkyne C C H H C
3 Bonds o o o
1 2 3
Alkyl Halide R X
Ether R O R The 0 is connected
H C C
to 2 carbon
C C X C C X C C X Nitrile R C N
H H C
o o o Nitro R NO2
1 2 3
Primary Secondary Tertiary

Amount of C Atom
 Functional Group Name Functional Group Name

Alkane O
R H
Carboxylic Acid R C OH
o
H
Amine 1 R N O
H Ester R C OR
R Lactone
o
-

is a nickname of ester
2 R N when both R's in f- ster c. meet O
H Ccyclic ester
C
Lactone O
R
o
3 R N
R O
Amide
O R C NH2
-

Lactam is nickname of amide

Aldehyde
a

R C H when both R & N Amite conned

in
O
C. cyclic Amide) C
O H
Lactam N
Ketone R C R

All of these are Carbonyl Compounds Cee Amine & Alkanet .

 Formula

Molecular Condensed Dash Bond-Line

H H Hydrogen Bond
Alcohol C2H6O CH3CH2OH H
H C C O H O
H H

H H
Ether CH3OCH3 C H O
H C O
H H
INDEX OF HYDROGEN DEFICIENCY
(IHD)
DEGREE OF UNSATURATION

 Ring

 Group 5  Increase
 Group 6  No Effect
 Group 7  Decrease

"

n
 AlkaneCAH Sigma)

3 1
& C4H10
-

IHD = 0
4 2 CnH2n+2

3 1
C4H8 IHD = 1
4 2
CnH2n
Alhere & Cyclo Alkane

4 1
C4H8 IHD = 1
3 2 CnH2n
 Origin of compound is AlKane
any

5 (Increase) ✗2
Group

a. C4H4N2
↓
C4H10
Effect)
+2
12 6CNo
Group
Whole Number Only ! !
b. C9H7OCl Decrease
)
7- (
In-12 Group
~

C9H20
-1

19

c. C2H6O2S
C2H6  Group 5  Increase
 Group 6  No Effect
 Group 7  Decrease
 APPROACH TO THE
AN
CLASSIFICATIONS OF ISOMERS
We can classify isomers (different
compounds that have the same molecular
formula) by asking and answering a series of
questions.
 H H
CH3CH2OH H C C O H
H H
C2H6O
H H
CH3OCH3
H C O C H
H H
 compounds have the
Do the
same molecular formula?

Yes No
Are they different? They are not isomers

Yes No
They are isomers They are identical

Do they differ in connectivity?

Yes No

They are constitutional isomers They are stereoisomers

 Constitutional Isomers
 Have same formula
 Have same IHD
 Have different connectivity

Stereo of Geometrical Isomers

 Have same formula

 Have same IHD
 Have same connectivity
 Have different arrangement of atoms in space
 H H
CH3CH2OH H C C O H
H H
C2H6O
H H
CH3OCH3
H C O C H
H H

CH3CH2OH & CH3OCH3 are Constitutional Isomers

 Constitutional Isomers of C4H9Br
IHD = 0
Br
CH3CH2CH2CH2Br CH3CHCH2CH3

n-isomer sec-isomer

CH3 CH3
CH3 CH CH2Br CH3 C Br
CH3

iso-isomer tert- or t-isomer

Constitutional Isomers of C4H9Br

Br n-Butyl Bromide
↳ when it's
Chika
. - -
i

Br
sec-Butyl Bromide

Br iso-Butyl Bromide

Br t-Butyl Bromide
 CH3
CH3 CH CH2CH2Br iso-Pentyl Bromide

CH3
t-Pentyl Bromide
CH3 C CH2CH3
Br

CH3
CH3 C CH2CH2Br neo-Hexyl Bromide
bhr there 1- & then CHECK ✗
CH3
is
-

cross
-

a
>
You Carbon
ring when
form 3 or more
can a you
 Since IHD > 0 Atleast one pior ring
.

Alkhibk:-b .

Nothing since it
has f. be 7.1-b42
for friary

cyclic Ether
 Geometrical Isomers

 Have same formula

 Have same connectivity
 Have same IHD
 Have different arrangement of atoms in
space
 Halogens can never be cyclic

Each C H H C2H2Cl2 Cl H Same Here

is
to
connected
14 &
C C C C
14 Cl Cl Cl
H
IHD = 1
A B
cis - isomer trans - isomer

 is not Zero H Cl
 is Zero
C C
H Cl
C

A & C are Constitutional Isomers

A & B are Geometrical Isomers
B & C are Constitutional Isomers
 C2H2ClBr

IHD = 1
H H Cl H
C C C C
Cl Br Br
H
A B
cis - isomer trans - isomer

Z - isomer E - isomer

A & B are Geometrical Isomers

 If
"

you have 4 Groups You trans

" " "
can't say cis or

C2HFClBr

IHD = 1

H F Cl F
C C C C
Cl Br Br
H
X Y
Z - isomer E - isomer

X & Y are Geometrical Isomers

 A

Not Isomers

ok CH? 9
it
¥
oh ok ay of
CHR

↳ tho 0
IHD -1
IHD -2
RESONANCE STRUCTURE
(R.S.)
 Bonds
Pi -

break
to
.

Change
Only they're
easy

because
 2ⁿᵈ Must stable
→
cuz Charges
are far

↓
Most stable Giz
0 charges
 Good Luck
Dr. Imad A. Abu-Yousef