CHAPTER TWO

REPRESENTATIVE CARBON
COMPOUNDS II
Electronegativity (E.N.) of some of
the elements

-0.5

L
 Chemical Bond

Covalent Polar Covalent Ionic

(E.N.) = 0 (E.N.) = 0 (E.N.) is Large

(Intermediate)

C C,O O ,H H C O,C N ,H O Na Cl

As the (E.N.) as the Polarity of the bond as the Bond Strength (B.S.)
 Intermolecular Forces

Weak
London Dispersion H-Bonding dipole-dipole
(L.D.) (O-H, N-H, H-F) (d-d)

CCl4, SiH4 H2O, NH3, CH3OH NF3, OF2, CH3OCH3

( = 0) ( = 0)
 → I

O O
H
H
↑
Intra Hydrogen Bonding
-

[
=L → 0 =L
More
Polarity

→
More
Rigid
 Diploe Moment ()

 = exd

 = Diploe moment (D)

e = charge in elecrostatic unit (esu), typically is on the order of 10-10
d = distance (cm), typically is on the order of 10-8
1 D = 10-18 esu.cm
↓
D is for Debye who got a Noble Prize in Chemistry in 1936 because of
his discovery.
 Note 8 We need to always use atleast one of these to
explain our answer

Important
Effects in Organic Chemistry

Inductive (Electronegativity) Effect

Polarizability (Size) Effect
Resonance Effect
Octet Rule (stability)
Example 1: The dipole moment of CHCl3 is larger
than the dipole moment of CFCl3. Explain.
[ Maybe ) Arrow goes
to the one
with the higher electronegativity

F H

C C
Cl Cl Cl Cl
Cl Cl
Example 2: The dipole moment of CH3Cl is larger
than the dipole moment of CH3F. Explain.

F Cl

C
C
H H
H H H
H
CH]f ( Ctf 4 because distance between atoms ed
is
greater µ
-

 = exd

Note: d (C-Cl) bond is >>> d (C-F) bond

Warning If the
: atoms belong to the same row, electronegativity effect is more

important factor then the atoms

size .
If
belong to same group ,
size factor
is more important .
 HOW TO NAME SIMPLE ORGANIC
COMPOUNDS?

l
Colts 664s -
Ork Colts - C

G CH2 G C G
↓
Ifbiscl

Phenyl Chloride
sp 3 sp or sp2

Phenyl Benzyl Benz

H H
C6H5 G C6H5CH2 G
H H or C6H6
or or
H H
Ph G PhCH2 G
Benzene
or
or

G H H
 G Bn
or H H Benzene
Bz G H H
H3C C G H C G

sp or sp2 sp2

Acet Form

G
G

sp 3 sp2

Allyl Vinyl
 "
CH3 in
Br ↑
H3C

'
a
g-
-

"
¥
a
O CH3
CH Allyl-iso-propyl Ether
CH3
d. C6H5CHO
G. Hs C
-

O
↑
C
H Benzaldehyde

e. CH3CH2COCH2CH3

O
C
CH3CH2 CH2CH3 Diethyl Ketone
 f. CH3CO2H
<
a-b-
O
↑
C Acetic acid
H3C OH If the Acet has 0 → × -

ic

Important
O
C
O CH2CH3 Ethylbenzoate
=

Ester
 h. CH2=CHN(CH2CH3)2
Ethyl
CH2CH3
H2C HC N CH2CH3 Diethyl vinyl amine

Tertiary
i. CH3CON(CH2CH3)(CH2C6H5)

O
CH2CH3
H3C C N N-Benzyl-N-ethyl acetamide
3
sp CH2C6H5

O
CH3
H C N N,N-Dimethyl formamide (DMF)
* ¥ ¥ q¥i¥-¥É¥ CH3
µ•*tkM*
Loft
 Acetonitrile

↳ 6
Double Bomb
between 5=4
 IHD = 1

Amide
Amid .

H Bond
-

Amide Amite
a. Three primary alcohols with the formula C5H12O.

IHD = 0
 IHD = 1

(Saturation)

If you switch these 2 it will be trans

 Dipole Moment is there with
cis & the previous one

CH3
H3C N CH2CH3
 0 ✗ can be =Y
11 but can't be H
Y C O X will be

Methyl formate
it
- -

SN
-

cuz

Ester an acid H - →

d Saturation -0
N is
connected to 7C
 Chloride

H
H
-

CH4 H3C Cl
-

> > Cl CH2 Cl

Methane Methyl Methylene

Alkane Akkene Could be Alkyne
could be not
Cl CH2 Cl

Methylene Chloride

H H
C C CH3CH2Br H2C CH2
H H Br Br

Ethylene or Ethene Ethyl Bromide Ethylene Bromide

 H2C CH2
OH OH

Ethylene Glycol or Ethylene Alcohol

HO OH OH OH
OH
Trimethylene Glycol Propylene Glycol n-Propyl Alcohol
or or
Trimethylene Alcohol Propylene Alcohol

Came from

be broke
←
pi bond
-

Propylene
H H
C C
H H O

Ethylene Ethylene Oxide or Oxirane or

Oxacyclopropane

H H
CH3
C C
H CH3 O

Propylene Propylene Oxide

 O

Oxetane or Oxacyclobutane
pentane
-

L
H O H H O H
H H <
We broke
pi
-bond
and added 4 Protons

H H Tetra Hydro H H
H H
TetraHydroFuran (THF) Furan
 Good Luck
Dr. Imad A. Abu-Yousef