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─ CC
2 3 ─ CH
4
3 2-butyne
Naming Alkenes & Alkynes
CH3─ CH2─ CC ─ 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
