Many areas rely on organic chemistry,

including:

Biology
Petroleum
Polymers
Genetic Engineering
Agriculture
Pharmacology
Consumer Products
22 - 1

22 - 2

H
H

C
H

H
C

22 - 3

22 - 4

22 - 5

22 - 6

Organic molecules can have very complex

structures.
A number of formats are used to represent
organic compounds.
Each has its own advantages but the goal is
the same, to accurately describe the
structure of a compound.
Lets look at some different representations.

 Similar to structural formula.

Each line represents a bond.
Carbons are assumed to be present at the end
of each line segment.
Hydrogen is not shown when bound to carbon.
OH

H2 H2
C C
H2C

CH2
C C
H2 H2

H2 H2
C C
H2C

H2C

H2 H2
C C
OH

C C
H2 H2

H2C

H2 H2
C C
H

H2C

C C
H2 H2

H2C

H2
C

C C
H2 H2

22 - 7

Three dimensional representations

CH3
22 - 8

Another key feature of carbon is its ability to

form double and triple bonds.
This can be between two carbons
alkenes (C=C) and alkynes (C C)
It can also be between carbon and another
element.
C=O
C=NC N

Both are models of propane.

22 - 9

22 - 10

22 - 11

22 - 12

cis-retinal

H3C

CH3

H3C
C=C
H

Light causes a
change from cisto trans-. This is
how we see.

C=C

light

CH3

several steps
O

22 - 13

trans-retinal

Several enzymes
are required
to convert
trans-retinal
Back to the
cis-form.
22 - 14

cis-

If you dont believe it,

give it a try!

trans22 - 15

CHO

CHO

HO

OH

CH2OH

CH2OH

H
CH2OH

Chiral center

CHO

CHO
HO

22 - 16

OH
CH2OH
22 - 17

22 - 18

Is the red carbon a stereocenter?

H!
HO!

H!
H3C-!
H!

H!
H3C-!
CH2CH3!

Cl!

I!

Br!

F!

H!H! H!
Cl!H! Cl!

22 - 19

22 - 20

Simplest members of the hydrocarbon family.

contain only hydrogen and carbon

only have single bonds
All members have the general formula of

CnH2n+2

Light is passed through a polarized filter.

A solution of an optical isomer will rotate the
light one direction.

Twice as many hydrogen

as carbon + 2!
22 - 21

22 - 22

These go up
as the number
of carbons
increases.!

22 - 23

22 - 24

Name

bp, oC

mp, oC

Density at 20 oC

Methane
Ethane
Propane
Butane
Pentane
Hexane
Heptane
Octane
Nonane
Decane

-161.7
- 88.6
- 42.2
-0.5
36.1
68.7
98.4
125.6
150.7
174.0

-182.6
-182.8
-187.1
-135.0
-129.7
- 94.0
- 90.5
- 56.8
-53.7
-29.7

0.000 667
0.001 25
0.001 83
0.002 42
0.626
0.659
0.684
0.703
0.718
0.730
22 - 25

22 - 26

heat or light

22 - 27

22 - 28

22 - 29

22 - 30

Prefix
MethEthPropButPentHexHeptOctNonDec-

Carbons
1
2
3
4
5
6
7
8
9
10

I see much
memorization in
your future!!

Lets practice some names

We will be leaving out the hydrogens.
This makes the carbon chain easier to see.
Its also easier
to draw!!

22 - 31

22 - 32

C!

C - C - C - C - C - C!

C - C - C - C - C!

22 - 33

22 - 34

Name the following.

(CH3)2CHCH2CH2CH(CH3)2
3,5-dimethyl heptane

This is a condensed structural formula.

3-ethyl-5-methylheptane

First convert it to a carbon skeleton, leaving

out the hydrogens.

2,3,3,7,8-pentamethyldecane
22 - 35

22 - 36

(CH3)2CHCH2CH2CH(CH3)2

1. Longest chain is 6 - hexane

C
C
|
|
C-C-C-C-C-C

2. Two methyl groups - dimethyl

3. Use 2,5-dimethylhexane

Now name it!

22 - 37

22 - 38

22 - 39

22 - 40

22 - 41

22 - 42

C-C-C-C-O-H

1. Follow the same system as with alkanes.

2. Give the name and carbon number for the
halide just like a side branch.
C-C-F

C-C-C

C-C-C-C-C

Cl

C-Br

22 - 43

22 - 44

The mechanism takes place in a single step.

This is supported by the observed rate law.
Rate = k [HO-][CH3Br]
SN2 reactions also take place with inversion
of configuration.
CH3

CH3

Cl

+ HO-

+ ClOH

22 - 45

H
!+

H O-

C
H

!-

Br

To account for the inversion,

the nucleophile must approach
from the back of the carbon
The nucleophile acts as a Lewis
base and the substrate as a
Lewis acid.

HO

22 - 46

Predicting whether an SN2 reaction will occur

is possible.

Br

The SN2 reaction

H H

Nuc:- + RX
H
!-

HO

!+

+ Br

C
H

is similar to a Bronsted-Lowry acid base

reaction
B:- + HX

22 - 47

RNuc + X-

HB + X22 - 48

H
C

Cl
C

-(CH2-CH2)-

)-(CH2-CH
|

Cl

22 - 49

22 - 50

Formula
Name

Monomer

Polypropylene

Polymer

CH3CH=CH2

( CH-CH2 )
|

CH3
Polystyrene

-CH=CH2

Polychloroprene H2C=CHC=CH2
|

( CH-CH2 )

( CH2CH=CCH2 )

Cl

Cl
22 - 51

22 - 52

Rad-CH2-CHCl + CH2
Rad

+ CH2 CHCl

CHCl

Rad CH2 CHCl

Rad-CH2-CHCl -CH2-CHCl
22 - 53

22 - 54

Adipoyl chloride
ClC(CH2)4CCl
||
||
O
O

Rad-CH2-CHCl -CH2-CHCl + Rad-CH2-CHCl -CH2-CHCl

Rad-CH2-CHCl -CH2-CHCl

CHCl-CH2-CHCl-CH2-Rad

hexamethylenediamine
+

H2N(CH2)6NH2

ClC(CH2)4C-NH(CH2)6NH2 + HCl
||
||
O
O

22 - 55

22 - 56

ClC(CH2)4C-NH(CH2)6NH2
||
||
O
O
HO

Product still has two reactive groups.

Polymer length is a function of time.

HO

O
HO

22 - 57

HO

O
HO

HO

O
HO

HO

O
HO

HO

22 - 58

crosslink

22 - 59

22 - 60