Organic Chemistry

What is organic chemistry?

• Organic chemistry is the study of compounds
that contain carbon
• Organic compounds are made of carbon and
hydrogen (and sometimes other elements like
oxygen, nitrogen, fluorine…) but ALWAYS carbon
and mostly hydrogen
• The simplest organic compounds are
hydrocarbons
• Hydrocarbons are only made of carbon and
hydrogen
 Alkanes
• The simplest hydrocarbons are the alkanes
• Alkanes only have single bonds
• Alkanes are unbranched (straight chained)
• There are three ways to show alkanes (for
example propane, C3H8):
– Full structure:
– Condensed structure:
– Molecular formula:
• Alkanes are “saturated” because each carbon
atoms are bonded to the maximum possible
number of other atoms
• The names of alkanes depend on the number
of carbons and all end in “-ane”
Number of Prefix Number of Prefix
Carbons Carbons
1 Meth- 6 Hex-
2 Eth- 7 Hept-
3 Prop- 8 Oct-
4 But- 9 Non-
5 Pent- 10 Dec-
 Alkyl Groups and Branched
Hydrocarbons
• Hydrocarbon chain can have “side branches”
which are also hydrocarbon chains
• For example,

• These attached “branches” are called alkyl

groups
• To name alkyl groups, change the ending to “-yl”
Naming Branched Alkanes (1 branch)
1. Find the parent chain
– Find the longest carbon chain
2. Choose a side to start counting
– Start counting from the side that gives the
smallest number to the branch
3. The number of the carbon where the branch
is attached to + “-” + name of alkyl + name of
parent alkane
 Examples
1.

2.

3.

4.
 Alkane with Multiple Branches
• If more than one different alkyl group is
attached to a hydrocarbon, then
1. List the alkyl groups in alphabetical order
2. Write the carbon number for each alkyl group
(you want to start numbering in the direction
that will give you the lowest possible numbers)
3. Put a dash “-” between the number and the alkyl
group
 Examples
1.

2.

3.
 Alkane with Multiple Branches
• If there are more than one of the same alkyl
group:
1. List each carbon number of each alkyl group
(even if there are 2 of the same alkyl group on
the same carbon)
2. Prefix the repeated group name by di, tri, tetra…
to show how many identical groups are attached
 Examples
1. 123

2. As

3. asdd
 Structural Isomers
• Structural Isomers: compounds that have the
same molecular formula but different
arrangements of atoms
• Example: C4H10 can be
 Cycloalkanes
• Alkanes that are connected in a head-to-tail
“circle”
• The word “cyclo-” is placed before the alkane
name
• Example:
 Substituted Cycloalkanes
• Cycloalkanes with alkyl groups attached
• To name substituted cycloalkanes:
• 1. If there is only one side branch (substituent), it
does not need a number
• 2. If there is more than one side branch, the first
side branch will be number 1 and the remaining
side branches will be number either clockwise or
counterclockwise as to have the lowest set of
overall values
 Examples
• 1. 3.

• 2.
 Alkyl Halides
• Alkyl halides are halogens (F, Cl, Br or I) attached
to alkanes
• Unlike alkyl groups, halogens can be placed on
the first carbon
• Attached halogens are named:
– F = fluoro
– Cl = chloro
– I = iodo
– Br = bromo
 Naming Alkyl Halides
• To name alkyl halides, follow the same rules as
naming branched alkanes
• The halogen branch follows the same rules as alkyl
groups
• The name of the halogen branch is placed first
then the parent alkane or cycloalkane
• If there is more than one type of side branch list
the names in alphabetical order
• If there is more than one of the same halogen,
place the prefix (di, tri, tetra…) before the halogen
name
 Example

• 1. 6.
• 2.

• 3.
• 4.

• 5.
 Alkenes and Alkynes
• Alkene: organic compound containing a carbon-
carbon double bond
• Alkyne: organic compound containing a carbon-
carbon triple bond
• Both alkenes and alkynes are called unsaturated
hydrocarbons because they have less hydrogen
atoms than equivalent alkanes
• Alkanes are saturated because they have the
maximum number of hydrogen atoms possible
Examples
 Rules for Naming Alkenes and Alkynes
1. a) If a double bond is present, change the “ane”
ending of the parent chain to “ene”
b) If a triple bond is present, change the “ane”
ending of the parent chain to “yne”
2. Use a number to indicate the location of the
double or triple bond when writing the parent chain
• Number the carbons so that the double or triple
bond has the lowest number
• The double or triple bond must go from the lower
numbered carbon to the carbon numbered one
higher (ex. C2 to C3 or C3 to C4 or C1 to C2)
 Notes
• An easy way to remember the endings is to
remember the endings in alphabetical order
• A of ANE is first, E of ENE is after and Y of YNE
comes last
• When naming alkanes, the carbons were
numbered so as to give the side branches the
smallest overall number
• In alkenes and alkynes, the double or the triple
bond has priority
• For cycloalkenes, the double bond must between
carbons 1 and 2
 Examples
1.
2.
3.
4.

5.
 Examples
1.
2.
3.
4.

5.
Cis and Trans Isomerism of Alkenes
• In alkanes, there are 4 bonds from the carbon
with each bond at 109.5˚
• This forms a tetrahedral shape
• In alkenes, the shape of the molecule is such
that three atoms connected to each carbon lie
flat, arranged 120˚ from each other
front view side view
• So the same alkene molecule can have two
different structures where the carbon chains
can be on the same side of the double bond or
in opposite sides of the double bond
• This is called cis-trans isomerism
• Isomerism refers to having the same name but
different structures
 Example
• There are two possible ways of having 2-
butene

and
 Cis Isomers
• In a “cis” isomer, the two groups of carbons are on
the same side of the double bond

• To name cis isomers, just write the word “cis-” in

front of the name
• For the structure above the name would be: cis-2-
butene
 Trans Isomers
• In a “trans” isomer, the two groups are “transverse”
or on opposite sides of the double bond

• To name a trans isomer, place the word “trans-” in

front of the name
• For the above structure, the name would be trans-
2-butene
 Benzene/Aromatic Compounds
• Benzene, C6H6, is an organic compound that
exists in a ring-like structure with 6 carbons
• Benzene can be written in either of the two
resonance structures, differing only in the
placement of the double bonds
• Each resonance structure consists of
alternation single and double bonds between
carbon atoms
 Actual Arrangement
• Although we can draw the structure in two
different ways, in reality, benzene exists a
mixture of both resonance structures
• Therefore, neither resonance structure is
actually correct
• To represent this situation of benzene, the
structure can be written as such:
 Aromatic Molecule
• Aromatic Molecule: a molecule containing one
or more benzene rings
• The aromatic ring (benzene ring) is frequently
shown as
• Many molecules that have benzene rings are
often fragrant and pleasant smelling
• Therefore, were given the name “aromatic”
 Naming Aromatic Molecules
• Naming aromatic molecules uses similar rules as
naming cycloalkanes
• With the exception that instead of writing the
parent cycloalkane name at the end, “Benzene” is
the parent
• Many aromatic compounds have their own special
name (you do not need to memorize these)
• You can also have structures that have more than
one benzene ring
 Example
1. 3.

2. 4.
 Functional Groups
• Functional Group: a specific group of atoms
which exists in a molecule and gives a
molecule an ability to react in a specific
manner or gives it special properties
• Hydrocarbons have a limited range of
properties and uses
• Adding one or more functional groups to a
hydrocarbon allows the molecule to have a
wide range of properties
• By adding the correct functional group,
chemists can make an organic molecule have
certain characteristics such as
– Make a molecule act as a base or acid or both
– Give the molecule a certain solubility
– Give a molecule a pleasant or unpleasant smell
– Make a molecule explosive
– Make a molecule react with specific chemicals
• There are 8 functional groups that we will look
at:
– Alcohols
– Esters
– Aldehydes
– Ketones
– Ethers
– Amines
– Amides
– Carboxylic Acids
• You need to know how to name alcohols and
esters. The others you only need to be able to
recognize the structure
 Alcohols
• Alcohol: organic compound containing an OH group
• Alcohols tend to have two opposing solubilities
– The OH group makes alcohols polar
– The hydrocarbon chain makes alcohols non-polar
• The shorter the hydrocarbon chain, the greater the
alcohol’s polar tendencies
• The longer the hydrocarbon chain, the greater the
alcohol’s non-polar tendencies
• This makes methanol, ethanol and propanols highly
soluble in water while pentanol and higher alcohols
are insoluble in water
 Naming Alcohols
• Number the hydrocarbon chain to give the
lowest number to the OH group
• Place the number immediately before the
name of the parent hydrocarbon
• Alkyl groups are placed before the number of
the OH group
• Change the “e” ending of “ane” to “ol” for
alcohol
 Examples
1.

2.

3.

4.
 Esters
• Ester: a compound in which a COO group
joins two hydrocarbon chains
• Esters are prepared by reacting an organic acid
(carboxylic acid) and an alcohol

• Esters, in general, have a very pleasant smell

and are often used in foods and cosmetics
 Naming Esters
• The hydrocarbon chain attached directly to
the carbon side of the COO group has its “e”
ending of “ane” changed to “oate”
– The C in the COO group is considered to be part of
the parent hydrocarbon chain

• There are 4 carbons, therefore, butanoate

• The hydrocarbon chain attached to the oxygen
(O) side of the COO group is named as an alkyl
group and is placed first

• Therefore, the name of this ester is:

methyl butanoate
 Examples
1.

2.

3.
 Aldehydes
• Aldehyde: organic compound containing C=O
group at the end of a hydrocarbon chain.
• The aldehyde group actually looks like
Or simply –CHO
Examples: 1. 2.

3. 4.
 Ketones
• Ketone: organic compound containing a C=O
group at a position OTHER THAN AT THE END
OF A HYDROCARBON CHAIN
• Examples: 1.

2.

3.
 Ethers
• Ether: compound in which an oxygen joins two
hydrocarbon groups
• Ethers have –O- between two hydrocarbon
chains
• Examples: 1.

2. 3.
 Amines
• Amine: organic compound containing an NH2
group. (or just N or NH)
• Amines are organic bases and react with acids
• Amines have a “fish-like” odor
• Examples: 1.
3.
2.
 Amides
• Amide: organic compound containing a CONH2
group (or CON-)
• The CONH2 group is shown as

• Examples:
1. 2.
3.
 Carboxylic Acids
• Carboxylic Acids: organic compound which
contains a COOH group.
• The COOH group is shown as
• Carboxylic acids are organic acids
• Examples: 1. 2.

3.
 Amino Acids
• Amino acid is a carboxylic acid with an amine
group at the 2-position
• Amino acids are the building blocks of proteins
• Since amino acids contain a carboxylic acid group
(which is an organic acid) and an amine group
(which is an organic base), it can behave as an
acid and a base
• Therefore, amino acids are highly soluble in
water
 Peptide Bond
• Amino acids will link with each other to form
longer chains called “dipepetide” for 2 amino acids
or “polypeptide” for more than 2 amino acids
• The two amino acids will bond to each other
through a peptide bond as shown

• The bond where two amino acids come together is

called a peptide bond
 Summary
Name Functional Group Name Functional Group

alkene ether

alkyne amine

halide amide

alcohol Carboxylic acid

aldehyde ester

ketone Aromatic ring

 Example
Identify all the functional groups present in each
molecule and label each group using:

1. 2.

3.