Organic Chemistry

For Dental Students

Dr. Nesma Mamdouh Bayoumy
Lecture (1)

Spring, 2015 1
An Introduction to Organic Compounds
Chapter 1
• Organic chemistry is that branch of chemistry that
deals with the structure, properties, and reactions
of compounds that contain carbon.

• Organic compounds are the compound which

contains mainly carbon and hydrogen.

2
 Hydrocarbons

Saturated Unsaturated
Alkanes
CnH2n+2

Alkenes Alkynes
C
CnH2n CnH2n-2

C C C C
 IUPAC Nomenclature
The Three Basic Parts
• The name for any organic molecule consists of three basic
parts:
Prefixes-Parent-Suffix

• Basic Part – Suffixes

• Suffixes on the end of the name of an organic molecule tell
you what major family the molecule belongs to

• The suffix for an alkane is “-ane”

• The suffix for an alkene is “-ene”
• The suffix for an alkyne is “-yne”
• Basic Part – the Parent
• The “parent” part of the name tells you how many carbons
are in the longest chain “main chain” of the molecule.
• Counting to Ten in Organic
• 01 = meth
• 02 = eth
• 03 = prop
• 04 = but
• 05 = pent
• 06 = hex
• 07 = hept
• 08 = oct
• 09 = non
• 10 = dec
• Parent and suffix…
• The parent is named based on the number of carbons
• 1 carbon = “meth”
• So a one-carbon alkane is called methane
CH4
• 2 carbons = “eth”
• So a two carbon alkane is called ethane.
CH3CH3
Parent and suffix…
• 3 carbons = “prop”
• So a three carbon alkane is called propane.
CH3CH2CH3
• 4 carbons = “but”
• So a four carbon alkane is called butane.
CH3CH2CH2CH3
• So name the following alkane (shown as both condensed
formula and a skeletal structure)
2 4 6 8

1 3 5 7 9
Answer?
nine
nine carbons
carbons +
+ alkane
alkane family
family =
= NONANE
NONANE

• Prefixes
• Prefixes are any substituent attached to the main chain
(parent) of the molecule.
• Prefixes – the Halides
• Chlorine is called “chloro”
• Fluorine is called “ Fluoro”
• Bromine is called “bromo”
• Iodine is called “iodo
Putting together a name…
•The rules for IUPAC nomenclature include:

•Step 1: Find the main chain (Longest chain)

•Step 2: Number the main chain

•Step 3: Identify all prefixes and their position numbers

•Step 4: Write the full name: Prefixes-Parent-Suffix.

•Step 5: Add punctuation.

o Put commas between numbers (2 5 5 becomes 2,5,5)
o Put a hyphen between a number and a letter (2 5 5
trimethylheptane becomes 2,5,5-trimethylheptane)
o Successive words are merged into one word (trimethyl heptane
becomes trimethylheptane)
 • Follow the rules… Name the following…
Br

4-Bromoheptane
Br
Br
CH3CH2CHCHCH2CH2CH3
Cl
Br
3,4-Dibromoheptane
3-Bromo-1-chloro-4-methylhexane

CH3CH2CHCH2CH2CH3 Br

Br
CH2CH3
1,1-Dibromo-3-methyloctane
ethylhexane-3
 • Alkyl Groups
• Alkyl groups are named similarly to alkanes.
• If you remove a hydrogen atom from one of these
you get an alkyl group.
• A fragment of methane, CH4, would be CH3- called “methyl”
• A fragment of ethane, CH3CH3, would be CH3CH2-, called
“ethyl”.
Example:

CH3CH2CHCH2CH2CH3
6 5 4 3 2 1
H3C CH CH2 CH CH CH3
CH2CH3
CH3 CH3 CH3
ethylhexane-3 2,3,5-Trimethylhexane
 IUPAC Systematic Nomenclature - Alkanes
•If compound has two or more chains of the same length,
parent hydrocarbon is chain with greatest number of
substituents.

Quiz
Draw Some Simple Alkanes:
2-methylpentane
3-ethylhexane
Example 1:  Write the structural formula for 2-
methylpentane
• Start from counting the number of carbon atoms in the
longest chain - pent counts 5 carbons.
• Are there any carbon-carbon double bonds?
• No – an tells you there aren't any.

•Now draw this carbon

skeleton:
• Put a methyl group on H H2 H2
H3 C C C C CH 3
the number 2 carbon
atom: CH 3

Write the structural formula:

2,3-dimethylbutane.
2,2-dimethylbutane.
3-ethyl-2-methylhexane.
4-bromo-3-methylhexene.
 Propyl Groups
•There are two possible three-carbon alkyl groups to form
from propane, CH3CH2CH3.
•The straight chain version: CH3CH2CH2- which is called
“propyl” or “n-propyl” (where n stands for “normal” or straight-
chained)

•The other possibility is to form the fragment on the central

carbon: CH3CHCH3, which is called “isopropyl”
 Name the following molecule:
• There are two options: Option 1 is highlighted in red:
• The red one has two branches

• Option 2 is highlighted in blue:

• The blue one has three branches

• Eight carbons in main chain. Octane.

• Three alkyl groups attached:
• 2-methyl
• 5-propyl
• 6-methyl
• Full name: 2,6-dimethyl-5-propyloctane.
Nomenclature of Substituents
• The name of the alkyl group followed by the name of the class
of compound constitutes the common name for alcohols
amines, and alkyl halides:
Function Class General Formula Suffix

Alcohols OH Ol

Aldehydes CHO al

Ketones C=O one

Ethers -O- ether

Esters -COO- oate

Carboxylic acids COOH- oic acid

Amines NH2 amine

 For each of the compounds A through G shown below, enter the
appropriate IUPAC suffix in the designated answer box. In the second
answer box enter a number indicating the number of carbon atoms in the
longest chain.
Compound IUPAC suffix Chain length

OH

H B

O
C

O
D
OH

E
OH

Cl CH 2 F
O

G
O CH 3
 Organic Chemistry
For Dental Students
Dr. Nesma Mamdouh Bayoumy
Lecture (2)

Spring, 2015 17
:Examples
OH OH

OH
3-methyl-2-pentanol 2,3-butanediol

O O O
ethylmethylether diethylether isopropylmethylether

O O O O

propanone 3-methyl-3-buten-2-one 2,4-pentanedione

:Name the following
OH
O O

HO HO
Cl

3-methylpentanoic acid but-3-enoic acid 4-chloro-5,5-dimethylhex

-1-en-3-ol

Br NH2

4-bromo-5,6-dimethylheptan-2-amine
3-ethyl-2,2,4,5-tetramethylhexane
:Name the following

Hexa-1,4-diene Pent-3-en-1-yne Hexa-1,3-dien-5-yne

Br

3,4-Dipropyl-1,3-hexadien-5-yne 4-bromo-7-methyl-2-nonene

5-fluoro-7,7-dimethyl-2,4-octadiene
Nomenclature of Cycloalkanes
• Cycloalkanes generally are shown as skeletal structures:
Nomenclature of Cycloalkanes
• Ring is the parent hydrocarbon unless the alkyl substituent has
more carbons; in that case the substituent becomes the parent
hydrocarbon.
If only one substituent, no need to give it a number:
Examples:

cyclobutylhexane propylcyclopentane 1,1,2-trimethylcyclobutane

Cl

2-chloro-1,3-dimethyl 3-isopropylcyclo
3-ethylcyclohept-1-ene
cyclohexane pent-1-ene
.The line formula for a cyclic compound is shown below

Give the IUPAC

name
Suffix

O Number of ring
carbons

The IUPAC name :

3-ethyl-5,5-dimethylcyclohept-2-en-1-one
The Suffix:
ONE
The number of carbons:
7 carbons
• A line formula for a compound is shown below.
• How many carbon atoms are in the root chain?
• Give the IUPAC name for this compound?

COOH

Cl
Answer:
Number of carbons 5
The IUPAC name:
4-chloro-2-ethyl-3-methylpent-4-enoic acid
Give the IUPAC name for the following

• 4-isopropyl-1-ethyl-2-propylcyclohexane

• 3-ethyl-1,5,5-trimethylcyclohexene

• 1-cyclohexylheptan-3-ol
OH

Br • 4-bromo-7-chloro-3-isopropylcyclo
Cl
hept-1-ene
 Benzene Derivatives
Cl Br C 2 H5 NO 2

ethylbenzene nitrobenzene
Chlorobenzene Bromobenzene

Br

1-methyl-2-propylbenzene
1-bromo-4-ethyl-2-isopropylbenzene

1,3,5-trimethylbenzene