INTRODUCTION TO ORGANIC

CHEMISTRY
 Organic Compounds

Typical organic compounds:

• Contain carbon
• Have covalent bonds
• Have low melting points
• Have low boiling points
• Are flammable (all burn)
• Are soluble in nonpolar solvents
• May be gases, liquids or solids
– Carbon: normally forms four covalent bonds and has no unshared pairs of
electrons.
C

– Hydrogen: forms one covalent bond and no unshared pairs of electrons.

– Nitrogen: normally forms three covalent bonds and has one unshared pair of
electrons.
N..

– Oxygen: normally forms two covalent bonds and has two unshared pairs of
electrons. ..
..O =

– Halogen: normally forms one covalent bond and has three unshared pairs of
..
electrons. .
. Cl
..
 Hydrocarbons

Large family of organic compounds

Composed of only carbon and hydrogen

Saturated hydrocarbons Unsaturated hydrocarbons

Alkanes Alkenes, Alkynes & Aromatics

H
H C H
C C
C-C C=C C C
C C
H C H
 Carbon

• Carbon has four valence electrons; hydrogen has one.

•
• C • H•
•

• To obtain an octet, carbon forms four bonds.

 Alkanes

General Formula

CnH2n+2
• Organic compounds can be named either using
common names or IUPAC names.

• You must be able to name alkanes, alkenes,

alkynes, and alcohols with 10 or fewer carbons in
the main chain using the IUPAC naming system.
• Alkane Nomenclature:
– Common alkyl groups (substituents):

CH3 methyl
Know these!

CH3CH2 ethyl
CH3CH2CH2 propyl
CH3CH2CH2CH2 butyl
1
CH3 - 2CH - CH3

3 CH2 - CH2 - CH2 - CH3

4 5 6
2-methylhexane
Give the name of: CH3

CH3─CH─CH2─CH3

STEP 1 Longest chain is butane.

STEP 2 Number chain. CH3


CH3─CH─CH─CH3
1 2 3 4

STEP 3 Locate substituent(s) and name.

2-Methylbutane
 Cl CH3
 
CH3─CH2─CH─CH─CH3

STEP 1 Longest chain is pentane.

STEP 2 Number chain from end nearest substituent.

Cl CH3
 
CH3─CH2─CH─CH─CH3
5 4 3 2 1

STEP 3 Locate substituents and name alphabetically.

3-chloro-2-methylpentane
 CH3 CH3
| |
CH3─CH─CH2 ─CH─CH3 2,4-dimethylpentane
1 2 3 4 5

Cl CH3
| |
CH3─CH2─CH─CH2─C─CH2─CH3
|
Cl
7 6 5 4 3 2 1

3,5-dichloro-3-methylheptane
 Br

CH3─CH─CH2─CH2─Cl

STEP 1 Longest chain has 4 carbon atoms.

C─C─C─C

STEP 2 Number chain and add substituents.

Br

C ─ C ─ C ─ C ─ Cl
1 2 3 4
STEP 3 Add hydrogen to complete 4 bonds to each C.
Br

CH3─CH─CH2─CH2─Cl 2-bromo-4-chlorobutane
Give the name of: CH 3 CH3
 
CH3─CH─CH─CH3

STEP 1 Longest chain is butane.

STEP 2 Number chain. CH3 CH3

 
CH3─CH─CH─CH3
1 2 3 4

STEP 3 Locate substituents and name.

2,3-dimethylbutane
Cyclic Hydrocarbon - Cycloalkane

Cyclobutane
=

= Cyclopentane

= Cyclohexane
Example: Write the condensed and line
structures for the following compounds:

3, 3-dimethylpentane

3-ethyl-2-methylhexane

2-methyl-4-propyloctane

1, 2-dichloro-3-methylheptane
 Physical Properties of Alkanes

• Nonpolar
• Insoluble in water.
• Lower density than water.
• Low boiling and melting points.
• Gases with 1-4 carbon atoms.
(methane, propane, butane)
• Liquids with 5-17 carbon atoms.
(kerosene, diesel, and jet fuels)
• Solids with 18 or more carbon atoms.
(wax, paraffin, Vaseline)
 Boiling & Melting points of Alkanes

Number of carbon atoms ↑ bp & mp ↑

Number of branches ↑ bp & mp ↓

CH3
CH3CH2CH2CH3
CH3CHCH3
 Chemical reactions of Alkanes
Low reactivity
2- Halogenation:
Alkanes react with Halogens.

CH4 + Cl2 CH3Cl + HCl

Chloromethane
Heat or light

Heat or light Dichloromethane

CH3Cl+ Cl2 CH2Cl2 + HCl

CH2Cl2+ Cl2 Heat or light CHCl3 + HCl Trichloromethane

Heat or light
CHCl3+ Cl2 CCl4 + HCl Tetrachloromethane
 Sources of Alkanes
• Natural gas
– 90 to 95 percent methane
– 5 to 10 percent ethane, and
– a mixture of other low-boiling alkanes, chiefly propane, butane, and 2-
methylpropane.

• Petroleum
– A thick liquid mixture of thousands of compounds, most of them
hydrocarbons formed from the decomposition of marine plants and
animals.
Alkenes and Alkynes
 Alkenes and Alkynes

Saturated compounds (alkanes):

Have the maximum number of hydrogen
atoms attached to each carbon atom.

Unsaturated compounds:
Have fewer hydrogen atoms attached to
the carbon chain than alkanes.

• Containing double bond are alkenes.

CnH2n

• Containing triple bonds are alkynes.

CnH2n-2
 Naming Alkenes & Alkynes
Using the IUPAC alkane names:

Alkene names change the end to -ene.

Alkyne names change the end to -yne
Give the location
for double and
triple bond
 Naming Alkenes & Alkynes

CH2= CH ─ CH2─ CH3 1-butene

1 2 3 4

CH3─ CH=CH─ CH3 2-butene

1 2 3 4

CH3
|
CH
4 3─ CH=C─CH
3 2 1 3
2-methyl-2-butene

CH
1
3─ CC
2 3 ─ CH
4
3 2-butyne
 Naming Alkenes & Alkynes

CH3─ CH2─ CC ─ CH3 2-pentyne

5 4 3 2 1

CH3

CH
5
3─ CH2─ C=CH ─ CH
4 3 2 1 3 3-methyl-2-pentene

CH2 – CH3
5 4 3 2 1

CH3─ CH2─ C=CH ─ CH3 3-ethyl-2-pentene

Example: Draw the condensed and line
structures for the following compounds:

2-chloro-3-methyl-2-butene

trans-3, 4-dimethyl-2-pentene

cis-6-methyl-3-heptene
Example: Name the following compounds:

CH3CH2C CCHCH3
CH2CH3
ClCH2CH2C CH
Example: Draw the condensed and line
structures of the following alkynes:

4-chloro-2-pentyne

3-propyl-1-hexyne
 Chemical properties of Alkenes & Alkynes

More reactive than Alkanes

Addition of Hydrogen (Hydrogenation-Reduction)

Addition of Hydrogen Halides (Hydrohalogenation)

Addition of water (hydration)

Addition of Bromine & Chlorine (Halogenation)

 Chemical properties

More reactive than Alkanes

Hydrogenation:
• A hydrogen atom adds to each carbon atom of a double bond.
• A catalyst such as platinum is used.

H H H H
│ │ Pt │ │
H–C=C–H + H2 H– C – C– H
│ │
H H
Ethene Ethane
 Chemical properties
More reactive than Alkanes

Halogenation:
• A halogen atom adds to each carbon atom of a double bond.
• Usually by using an inert solvent like CH2Cl2.

H H H H
│ │ │ │
CH2Cl2
CH3–C=C–CH3 + Cl2 CH3– C – C– CH3
│ │
Cl Cl
2-Butene 2,3-Dichlorobutane
Chlorination of Propane

30%

70%
H’s are not abstracted at the same rate.

For secondary:
70%/4H = 17.5
For primary:
30%/6H = 5.0
Therefore…
Relative rate of H abstraction for 1o : 2o is
1 : 3.5
3o Radicals are Easiest to Form
Tertiary H’s removed five times more readily
than primary H’s in chlorination reactions

Relative reactivity of 1o H abstraction:

65% / 9H = 7.2

Relative reactivity of 3o H abstraction:

35% / 1H = 35
Therefore…
Relative rate of H abstraction for 1o : 3o
1:5
Stability of Free Radicals
 Functional Groups
Class of Compound Functional Group

Alcohol C OH

Ether C O C

O
Aldehyde
C H
O
Ketone C C C

O
Carboxylic Acid C OH

O
Ester
C O C
 Functional Groups
Class of Compound Functional Group

R
Amine C N
R'
O
R
Amide C N
R'

Nitrile C N
 Alcohol H CH
CH C OCH
H
3 2 2
H
H
H O H H H (CH3CH2)2O
H H H H
OH
H CCH3C
CH(OH)CH
C C 2CCH(CH )2 3CH(OH)CH2CH(CH3)2
H 3CH
H C C O C C H
H H H H
H C H H CH
CH H OCH CH H H
3 2 2 3
CH3CH(OH)CH CH(CH3)2 H
Ether H 22
3 3 2 H H H H
(CH CH ) O
H OH
H H H H O H3 H2 2 H H C C C C
CH3C
C CH2OCH
C C CHH
H C C O C CH HC 3 OH
2 2
2 3
3 H OH H H
H H H H HH H HH H
H HH(CH H
CH2)2O
H H H H H
3
3
C
2 2
H
H C C C C C N C CH3CH2CH2CH
H
H C O
CAmine C C H H H HH H H H H
H
H HH HHOHH H
H OH
H H O N
H C C C C C N C
CH3CH2CH2CH2CH2NHCH3
H
H H H H H H H
 H O
CH3NH2 CH3NHCH3 (CH3)3N
o o
H O3
o H C C H
1 2 CH3C(O)CH3
primary secondary tertiary H
H C C H
H H O H
Aldehyde
H O H CH
C 3CHO
C C H
H C C H CH3CHO HO H
H O H
CH3C(O)CH3
CH3CHO
Ketone H
CH3CHO O H
H O H CH3C(O)CH3
O O H
H H C
C C C H H H C
H C H
H H OC H
H H C
O H
H
 H C C C O H CH3CH2CO2H
Carboxylic acid
H H
H H O H H O H H OH
H C C C O H HCH3CCHHCO2H
2C CH O C CO H
H
H H H C H C C O H CH C H
H
OH
Ester H H H H
CH3
CH2CO2H CH CH CO CH
O 3 2 2 2 3 CH
H H O H H HCHH3CHO
2
CO2CHH
2
CH3H O
OH
H C C C O C C H
H CH HC C N H C C H O O
H
H HO H H H H H O H H
H H C H HO H C H HHH O
H CC CC C CN C C H
CHAmides
CH2CO2CH2CH3
H H
3 HHHCHHCHOC O
H
H H H CCH
CONHCH H H
C3 2 C C 2 3 H
H H O H H O H
H O HH N
H C CH C N C
H C H CH CH CONHCH CH
H O 3 2 2 3
HH H H H H H H R = alkylHgroup
-CO2R where O
H C O C H O
C C C H
Write a structural formula for
A. 2-pentanamine

B. N-methyl-1-butanamine
Give a name for each:
A. CH3—NH—CH2—CH3

CH3
|
B. CH3—CH2—N—CH2—CH2—CH2—CH3
A. CH3—NH—CH2—CH3
ethylmethylamine; N-methylethanamine

CH3
|
B. CH3—CH2—N—CH2—CH2—CH2—CH3

N-ethyl-N-methyl-1-butanamine
 Example: Identify the functional groups present in the following
compounds.

OH
I I NH2
HO O CH2CHCOOH
I I O

thyroxine testosterone
 NH

HO2C
N
N
Example: Identify the functional groups in the following
O
compounds. H C
O
NH2
O
C H
HO2C
N
N
H O C OCH3
O OH OH

Lisinopril Vanillin
Aromatic Hydrocarbons
 Aromatic Compounds

Aromatic compounds contain benzene.

Benzene has:

• 6 C atoms and 6 H atoms.

H H
• Two possible ring structures. H C H H C H
C C C C
C C C C
H C H H C H
H H
 Aromatic Compounds

Arene: A compound containing

H one or more benzene rings.
H C H
C C
C C
H C H Naphthalene
Aromatic compounds are named:
H
A Kekulé structure A Kekulé structure
showing
• With benzene all atoms
as the parent chain. as a line-angle formula
• Name of substituent comes in front of the “benzene”.

CH
CH CH2 CH3
CHCl CH=CHCHCH
CH-CH
CH CH=CHC
3 2 CH3 2 3 22 3 3
3 2

methylbenzene chlorobenzene ethylbenzene

Ethylbenzene Ethylbenzene
Toluene Toluene
Ethylbenzene Styrene
Styrene Tolu
 Naming of Aromatic Compounds
Some substituted benzenes have common names.
O
CH3
OH OH
OCH OCH
NH NH
3 2 3 C-H
2

Phenol
Toluene Phenol Aniline
Anisole AnisoleBenzaldehyde
Aniline Ben

O O
OH OCH3 NH2 C-H C-OH

enol Anisole Aniline Benzaldehyde Benzoic acid

 Naming of Aromatic Compounds

When two groups are attached to benzene, the ring is numbered to give
the lower numbers to the substituents.

- Start numbering from special name (if we have).

- If we do not have, number them to get the smallest set of numbers.
- Name them by alphabetical order.

COOH CH2 CH3

CH3 4
1
2 Br 1
3
2

3 2
CH3 1
3-methyltoluene Cl
2-Bromobenzoic acid 1,3-Dimethylbenzene 1-Chloro-4-ethylbenzene
(o-Bromobenzoic acid) (m-Xylene) (p-Chloroethylbenzene)

Ortho Meta Para

 Naming of Aromatic Compounds
If we have three or more substituents:

-Start numbering from special name (if we have).

-If we do not have, number them to get the smallest set of numbers.
-Name them by alphabetical order.

CH3 OH NO2
1
2 NO2 Br 6
1
2 Br 4
3

2
3 5 3
4 4
1
Br
Cl Br CH2 CH3
4-Chloro-2- 2,4,6-Tribromophenol 2-Bromo-1-ethyl-4-
nitrotoluene nitrobenzene
 Chemical properties of benzene
H H
H C H H C H
C C C C
Resonance: stable
C C C C
H C H H C H
H H

No addition reactions (almost unreactive)

Halogenation

Nitration

Sulfonation
 Chemical properties of benzene

Halogenation

Fe Cl3
H + Cl2 Cl + HCl

Benzene Chlorobenzene

Nitration

H2 S O4
H + HNO3 NO2 + H2 O

Nitrobenzene
Amino Acid
Some Amino Acids
Some More Amino Acids