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Introduction to
Organic Chemistry
BIOB111
CHEMISTRY & BIOCHEMISTRY
Session 7
Key concepts: session 7From this session you are expected to develop an understanding of the following concepts:
Concept 1: Organic compounds
Concept 2: Organic vs inorganic compounds
Concept 3: Individual atoms vs atoms within a compound
Concept 4: Covalent bonding of a carbon atom
Concept 5: Saturated vs unsaturated hydrocarbons
Concept 6: Straight-chain vs ring structured hydrocarbons
Concept 7: Properties of a functional group
Concept 8: Number of functional groups in a compound
Concept 9: Stereoisomers
These concepts are covered in the Conceptual multiple choice questions of tutorial 7
Session OverviewPart 1: Exploring the formation of compounds
• Organic vs inorganic compounds
• Atoms connect together to form compounds
• Covalent bonding of carbon atoms
• Covalent bonding of common non-metal atoms
Part 2: Drawing and interpreting organic compounds
• Representations of organic compounds
• Saturated vs unsaturated hydrocarbon compounds
Part 3: Chemical reactivity of organic compounds
• Functional groups
• Stereoisomers
Part 1: Exploring the formation of compounds
• Organic vs inorganic compounds
• Atoms connect together to form compounds
• Covalent bonding of carbon atoms
• Covalent bonding of common non-metal atoms
Organic compounds:
Compounds that contain one or more
carbon atoms are organic compounds
• Organic compounds are required for
life to exist:
– Carbohydrates, lipids, proteins, fats and
nucleic acids (DNA and RNA) are all
large organic compounds
Each line connecting the atoms below represents a
covalent bond (2 electrons shared between the two connected atoms)
Organic vs inorganic compounds
Hydrocarbon derivatives
Life on earth would not exist without organic compounds that contain carbon atoms
• Our genetic material (DNA) contains many carbon atoms
• Our bodies rely on the organic compounds below to function:
– Proteins are made up of amino acids
– Lipids are often made up of fatty acids (long hydrocarbons) and glycerol
– Carbohydrates are made up of one or more monosaccharide (sugar) units
Inorganic compounds:
Compounds that do not contain any carbon atoms are inorganic compounds
• Examples of inorganic compounds:
– NaCl (table salt)
– H2O (water)
– NH3 (ammonia)
O
HH
Each line connecting the atoms below represents a
covalent bond (2 electrons shared between the two connected atoms)
Organic vs inorganic compounds
https://www.freeimages.com/photo/water-drop-1501587
Water is a vital compound for the human body• 50 to 65% of the average human body is made up of water (H2O)
• Water is needed to transfer components between cells that make up the human body
Organic vs inorganic compounds
Inorganic compounds• Do not contain any
carbon atoms
Organic compounds
• Contain one or more carbon
atoms
• Usually covalent compounds,
which contain two or more
non-metal atoms
• Some inorganic compounds are covalent compounds and some are ionic compounds
– H2O (covalent compound)
– NaCl (ionic compound)
Hydrocarbon
Organic vs inorganic compounds
Hydrocarbon compounds:
The most basic organic compounds are hydrocarbons
– Hydrocarbons contain only carbon and hydrogen atoms
– Hydrocarbons compounds are created in nature
and can be synthesised in the laboratory
Structures of Hydrocarbon compounds
Each line connecting the atoms below represents a covalent bond (2 electrons shared between the two
connected atoms)
Organic vs inorganic compounds
Atoms within a compound are
more stable than individual
atoms
Atoms connect together to form compounds
OH H
Oxygen and hydrogen atoms in a H2O molecule are stable
• Each atom has a full valence electron shell
Separate oxygen and hydrogen atoms are unstable
• Each atom does nothave a full valence electron shell
– Atoms within a compound have a
full outer (valence) electron shell
which imparts stability
(unreactive)
– Individual atoms do not have full
valence electron shells (unless
they are noble gases)
Nucleus
Electron
Proton
Neutron
Shell 1 Shell 2
Unpaired electron
Paired electrons
• The subatomic particle
responsible for chemical
bonding are the atom’s electrons
– Specifically, the atom’s unpaired
valence electrons
An atom’s valence electron shell is the shell furthest away from the nucleus• The valence electron shell is also
known as the outer electron shell– In the diagram, shell 2 is the valence
shell
– In this case, shell 2 contains both paired electrons and unpaired electrons
Atoms connect together to form compounds
VALENCE
ELECTRONS
Can be
PAIRED ELECTRONS
STABLE
UNPAIRED ELECTRONS
Can be
UNREACTIVE
DO NOT CONTRIBUTE TO CHEMICAL
BONDING
Are Are
UNSTABLE REACTIVE
CONTRIBUTE TO CHEMICAL BONDING OF
THE ATOM
Are Are
Atoms connect together to form compounds
Electron
Proton
Neutron• Each element’s atoms have a
specific number of valence electrons– Number of valence electrons:
• Carbon has 4
• Oxygen has 6
• The group number of a representative element (group A) is equal to the number of valence electrons in the atom
Nucleus
Shell 1 Shell 2
Unpaired electron
Paired electrons
• Carbon is in group IV,
so it contains 4 valence electrons
• Oxygen is in group VI,
so it contains 6 valence electrons
Atoms connect together to form compounds
Lewis Symbols
• The number of valence electrons in a representative element is the same as the elements Group No.
• The maximum number of valence electrons for any element is 8 – electron octet
Stoker 2014, Figure 4-1 p87
Electron-Dot Symbols for the first 20 elements on the periodic table (below)Chemical symbol of the element surrounded by dots, with each dot representing the number of valence electrons in the atom
Atoms connect together to form compounds
N
Electron
Paired valence electrons = non-bonding electrons
Unpaired valence electrons =
bonding electron
N H
H
HCovalent bond = 2 electrons shared betweenthe 2 participating atoms
N H
H
H
Simplified representation
NH3 is the covalent compound ammonia
Atoms connect together to form compounds
The Octet Rule: Atoms LOSE, GAIN or SHARE their valence electrons (through chemical bonding) to obtain 8 valence electrons in their outer shell
Non-noble gas atoms form chemical bonds with each other to fill their valence electron shells (obtain 8 electrons)
– Allows the non-noble gas atoms to mimic the electron arrangement of a noble gas to become very stable
Noble gases naturally have 8 valence electrons
• Noble gases are very stable and unreactive, as they have satisfied the octet rule
– Noble gases do not react with other atoms to form chemical bonds
Noble gas: neon Non-noble gas: nitrogen
After covalent bondingNe
.... .. .. ..N. .. ..N......
• An atom that has satisfied the octet rule (has 8 electrons in the valence shell) is stable
– The Octet rule applies to group A (Representative) elements,
but not transition elements
Atoms connect together to form compounds
A CHEMICAL BOND IS A CONNECTION
BETWEEN TWO ATOMS
The basis of the connection between atoms is either:
TWO ATOMS SHARING ELECTRONS
COVALENT BONDING
Is called
ONE ATOM DONATING ELECTRON(S) TO ANOTHER ATOM
BOTH ATOMS BECOME IONS
Through this process
IONIC BONDING
Is called
The atoms within organic compounds are connected via
covalent bonds
Atoms connect together to form compounds
COVALENT BOND
SHARED PAIRS OF ELECTRONS COUNT
TOWRDS THE ELECTRON TOTAL FOR BOTH ATOMS
OXYGEN HAS 8 VALENCE
ELECTRONS
ALLOWS TWO ATOMS TO CONNECT VIA SHARING A
PAIR OF ELECTRONS
Definition
Example
EACH HYDROGEN HAS 2 VALENCE
ELECTRONS
H2O
Covalent bond
ALL ATOMS IN THE COMPOUND
HAVE FULL VALENCE
ELECTRON SHELLS AND ARE
STABLE
Simplified representation
Covalent bond
Atoms connect together to form compounds
ATOMS FORM AS MANY COVALENT BONDS AS REQUIRED TO OBTAIN 8 VALENCE ELECTRONS
NUMBER OF UNPARIED VALENCE ELECTRONS = NUMBER OF COVALENT BONDS NEEDED TO FORM THE ELECTRON OCTET (8 VALENCE ELECTRONS)
H2O
RULE
OXYGEN IS IN GROUP VI,
SO IT CONTAINS 6 VALENCE ELECTRONS
2 unpaired valence electrons
HYDROGEN IS IN GROUP I,
SO IT CONTAINS 1 VALENCE ELECTRON
1 unpaired valence electron
OXYGEN HAS 8 VALENCE ELECTRONS, AFTER FORMING 2 COVALENT BONDS
EACH HYDROGEN HAS 2 VALENCE ELECTRONS, AFTER FORMING 1 COVALENT BOND
..O... H
. .
How can individual atoms increase their stability?
In the below structure each carbon atom forms 4 covalent
bonds and each hydrogen atom forms 1 hydrogen bond
Covalent bond (2 shared electrons)
– To achieve stability, each atom must form a specific number of chemical bonds to fill its valence electron shell
– The atoms that make up organic compounds form covalent bonds to fill their valence electron shells to become stable
Atoms connect together to form compounds
1. What groups are hydrogen and carbon
in on the periodic table?
2. How many valence electrons do hydrogen
and carbons atoms contain?
3. Draw the Lewis symbol for the hydrogen and
carbon atoms.
4. How many covalent bonds must the carbon and hydrogen
atoms form to be stable (have full valence electron shells)?
How many covalent bonds must the carbon and hydrogen atoms form to be stable (have full valence electron shells)?
Hint: look at the structure on the right
Covalent bond (2 shared electrons)
The atoms that make up organic compounds
form covalent bonds to fill their valence
electron shells and become stable
• Carbon is in group IV and contains 4 unpaired valence electrons
– Carbon atoms must form 4 covalent bonds to be stable
• Hydrogen is in group I and contains 1 unpaired valence electrons– Hydrogen atoms must form 1 covalent bond to be stable
Atoms connect together to form compounds
Covalent bonding of carbon atomsThe huge diversity of the different organic compounds is due to:
• The capacity of carbon atoms to form carbon to carbon covalent bonds
– Carbon can form short or long-chain hydrocarbon compounds in a huge array of different configurations
Stoker 2014, p119
Covalent bonding of carbon atoms
C
CarbonContains 4 unpaired valence electrons
Each unpaired valence electron can form 1 covalent bond
Carbon forms 4 covalent bonds to obtain8 valence electrons
• Carbon belongs to Group IV (A), meaning it has 4 unpaired valence electrons
– Carbon shares its unpaired valence electrons with other atoms to acquire 4 shared pairs of electrons = 4 covalent bonds
– Once carbon has formed 4 covalent bonds: • It has 8 valence electrons and has satisfied the
octet rule
• For a carbon atom to be stable, it must form 4 covalent bonds
– Every carbon atom in a compound must have 4 covalent bonds (imparts stability)
Covalent bonding of carbon atoms
What is the basis for the huge diversity of
organic compounds?
– The ability of carbon atoms to form covalent bonds with other carbon atoms and other non-metal atoms such as hydrogen (H), oxygen (O), nitrogen (N) and sulfur (S)
– Each carbon atom has 4 unpaired electrons in its valence shell
>>> each unpaired electron can participate in one covalent bond
• Total covalent bonds formed by a carbon atom = 4
FULL VALENCE
ELECTRON SHELL
CARBONATOMS
FORM 4 COVALENT
BONDS
To achieve a
Form
NITROGENATOMS
FORM 3 COVALENT
BONDS
Form
OXYGEN ATOMS
FORM 2 COVALENT
BONDS
Form
HYDROGENATOMS
FORM 1 COVALENT
BOND
Form
HALOGENATOMS
(CHLORINE AND FLOURINE)
FORM 1 COVALENT
BOND
Form
To achieve a To achieve a To achieve a
To achieve a
Covalent bonding of common non-metal atoms
Essential knowledge to interpret and
draw the structures of hydrocarbon compounds:
• Carbon atoms always form 4 covalent bonds within a compound
• Nitrogen atoms always form 3 covalent bonds within a compound
• Oxygen atoms always form 2 covalent bonds within a compound
• Hydrogen atoms always form 1 covalent bond within a compound
• Halogen atoms (e.g. fluorine and chlorine) always form 1 covalent bond within a compound
Covalent bonding of common non-metal atoms
NitrogenContains 3 unpaired valence electrons
Nitrogen forms 3 covalent bonds to obtain 8 valence electrons
C
CarbonContains 4 unpaired valence electrons
Each unpaired valence electron can form 1 covalent bond
Carbon forms 4 covalent bonds to obtain8 valence electrons
N
Hydrogen and halogen atomsContain 1 unpaired valence electron
Hydrogen forms 1 covalent bond to obtain 2 valence electrons
Halogen atoms such as chlorine and fluorine form 1 covalent bond to obtain 8 valence
electrons
OxygenContains 2 unpaired valence electrons
Oxygen forms 2 covalent bonds to obtain 8 valence electrons
OFH
H
F
Covalent bonding of common non-metal atoms
Electron
Unpaired valence electrons =
bonding electron
C H
H
HCovalent bond = 2 electrons shared betweenthe 2 participating atoms
C H
H
H
Simplified representation
CH4 is the organic hydrocarbon
compound methaneHHC
HCarbon forms 4 single covalent bonds with 4 separate hydrogen atoms
Covalent bonding of common non-metal atoms
C
H
H
Double Covalent bond = 4 electrons shared betweenthe 2 participating atoms in two separate covalent bonds
C
H
H
Simplified representation
CH2O is the organic compound
formaldehyde
OO
Electron
Unpaired valence electrons =
bonding electron
C
H
OPaired valence electrons = non-bonding electrons
Carbon forms 1 double covalent bond with oxygen and 2 single covalent bonds with separate hydrogen atoms
CDouble Covalent bond = 4 electrons shared betweenthe 2 participating atoms in two separate covalent bonds
C
Simplified representation
CO2 is the organic compound
carbon dioxide
O
O
OO
Electron
Unpaired valence electrons =
bonding electron
C
O
Paired valence electrons = non-bonding electrons Carbon forms 2 separate double covalent bonds with oxygen
Covalent bonding of common non-metal atoms
CHTriple Covalent bond = 6 electrons shared betweenthe 2 participating atoms in three separate covalent bonds
C
HSimplified
representation
CHN is the organic compound
hydrogen cyanide
N
N
Electron
Unpaired valence electrons =
bonding electron
C
H
Paired valence electrons = non-bonding electrons
NCarbon forms 1 triple covalent bond with nitrogen and 1 single covalent bond with a hydrogen atom
Covalent bonding of common non-metal atoms
Using single and double covalent bonds,
draw three different compounds that could
form between 1 carbon atom (C),
2 oxygen (O) atom
and 4 hydrogen atoms (H)
Note: not all atoms have to be present in each compound
When a carbon atom is part of an organic compound,
how full is its valence (outer) shell? Why?
How does the octet rule relate to the number of
covalent bonds that a carbon atom
forms within an organic compound?
Are the carbon atoms within an organic compound
more or less stable than individual atoms
not part of a compound? Why?
Key concept: valence shell, octet rule, atom/compound stability
Attempt Socrative questions: 1 to 4
Google Socrative and go to the student login
Room name:
City name followed by 1 or 2 (e.g. PERTH1)
1 for 1st session of the week and 2 for 2nd session of the week
Part 1: Exploring the formation of compounds
• Organic vs inorganic compounds– Organic compounds contain one or more carbon atoms, whereas inorganic
compounds do not contain any carbon atoms
– Organic compounds are usually covalent compounds which contain covalent bonds connecting the atoms
– Hydrocarbon compounds are a type of organic compound that contains only carbon and hydrogen atoms
• Atoms connect together to form compounds– Atoms connect together via chemical bonds to form compounds, allowing the
atoms to become stable
– The atoms in organic compounds form covalent bonds to fill their valance electron shells, as atoms that contain full valence electron shells are stable
– Atoms within compounds are more stable than atoms not part of a compound
Part 1: Exploring the formation of compounds
• Covalent bonding of carbon atoms– Carbon belongs to group IV (A) in the periodic table, so it contains 4
unpaired valence electrons
– For a carbon atom to be stable, it must form 4 covalent bonds, which allows each of its unpaired valance electrons to become part of a shared pair of electrons (covalent bond)
– Carbon atoms can form single, double or triple covalent bonds to other atoms to have a total of 4 covalent bonds
– Once a carbon atom has formed 4 covalent bonds, the carbon atom has 8 electrons in its valance electron shell and has satisfied the octet rule
Part 1: Exploring the formation of compounds
• Covalent bonding of common non-metal atoms
– Each non-metal atom must form a specific number of covalent bonds
to achieve a full valence electron shell, which satisfies the octet rule
– To achieve a full valence electron shell:
• Nitrogen atoms form 3 covalent bonds
• Oxygen atoms form 2 covalent bonds
• Hydrogen atoms form 1 covalent bond
• Halogen atoms (such as chlorine and fluorine) form 1 covalent bond
Part 2: Drawing and interpreting organic compounds
• Representations of organic compounds
• Saturated vs unsaturated hydrocarbon compounds
How can the structures of organic compounds be represented?
– Molecular formula
– Complete structural formula
– Condensed structural formula
– Line bonding formula
Representations of organic compounds
Molecular formula
– Indicates the number of each type of atom present in the
compound
• Gives no information about the arrangement of the atoms within the
compound or molecule
C3H8The molecular formula above specifies that there are:• Three carbon atoms • Eight hydrogen atoms • Provides no information about how the atoms are arranged within the compound
Representations of organic compounds
Complete Structural formula
– Shows every covalent bond between
the atoms within the compound as a line
• Gives the most complete information about the arrangement
of the atoms within the compound or molecule
The complete structural formula specifies that there are:• Three carbon atoms • Eight hydrogen atoms• Provides comprehensive information about how the atoms are arranged within the compound
Representations of organic compounds
Condensed structural formula
– Specifies the structural formula using text
• Provides information about the arrangement of the atoms
within the compound or molecule
CH3CH2CH3The condensed structural formula above specifies that there are:• Three carbon atoms • Eight hydrogen atoms • Provides information about how the atoms are arranged within
the compound• CH3 is connected to a CH2 which connects to another CH3
Representations of organic compounds
Condensed structural formula
– Specifies the structural formula using text
• Provides information about the arrangement of the atoms
within the compound or molecule
CH3CH2CH3Structural formula
Shows the number of hydrogens
bonded to each carbon atom
Line bonding formula
– At the end of each line is a carbon atom,
with the lines representing the bonds between carbon atoms
• Compounds that contain atoms other than carbon and hydrogen can be shown in a line bonding formula, where the non-carbon atoms are represented by their chemical symbols
CH3CH2CH3The line bonding formula above shows the:• Chemical bonds between the carbon atoms within the compound• Hydrogen atoms are not shown • No atoms other than carbon or hydrogen are present so no chemical symbols are shown
Condensed structural formula
Line bondingformula
Representations of organic compounds
Line bonding formula
– At the end of each line is a carbon atom,
with the lines representing the bonds between carbon atoms
Line bonding formula
At the end of each line is a carbon
atom, with the lines representing
the bonds between carbon atoms
F
Complete structural formula
Shows all covalent bonds as lines between atoms
CH2CHCH3
Condensed structural formulaShows the number of hydrogens
bonded to each carbon atom
Line bonding formulaAt the end of each line is a carbon
atom, with the lines representing
the bonds between carbon atoms
Molecular formulaShows the number of
each type of atom present
C3H6
Exercise:
Draw the following hydrocarbon structure in the:
complete structural formula
line bonding formula
1. CH3CH2CH2CH3
2. CHCCH3
Exercise:
Draw the following hydrocarbon structure in the:
complete structural formula
line bonding formula
Exercise:
Draw the following hydrocarbon structure in the:
complete structural formula
condensed structural formula
3.
Hydrocarbon compounds:
The most basic organic compounds are hydrocarbons
– Hydrocarbons contain only carbon and hydrogen atoms
– Hydrocarbons compounds are created in nature
and can be synthesised in the laboratory
Structures of Hydrocarbon compounds
Each line connecting the atoms below represents a covalent bond (2 electrons shared between the two
connected atoms)
Organic vs inorganic compounds
HYDROCARBONSType
SATURATED HYDROCARBON
CONTAIN ONLY SINGLE CARBON TO
CARBON BONDS
ORGANIC COMPOUNDS THAT CONTAIN CARBON AND HYDROGEN ATOMS
CONTAIN ONE OR MORE DOUBLE OR TRIPLE CARBON TO CARBON BOND,
ALSO CONTAIN ONE OR MORE SINGLE CARBON TO CARBON BONDS
UNSATURATED HYDROCARBON
Type
Definition
Definition
Definition
UNREACTIVE
Are
REACTIVE
Are
Due to
LARGE AMOUNT OF ENERGY NEEDED TO BREAK THE SINGLE BONDS PRESENT
Due to
DOUBLE AND TRIPLE CARBON TO CARBON BONDS CAN EASILY BE
BROKEN IN A CHEMICAL REACTION
Unsaturated hydrocarbons• Contain one or more double or
triple carbon to carbon bond– Are also likely to contain one or
more single carbon to carbon bonds
Saturated hydrocarbons
• Contain only single carbon to
carbon bonds
• Unreactive and stable– Due to the large amount of energy
needed to break the existing chemical
bonds
• Reactive and unstable (compared to saturated hydrocarbons)
– Due to the small amount of energy required to break the double or triple carbon to carbon bonds present
Saturated vs Unsaturated hydrocarbon compounds
Saturated Hydrocarbons
– Saturated hydrocarbons have only single carbon to carbon bonds
Saturated vs Unsaturated hydrocarbon compounds
– The carbon atoms in saturated hydrocarbons form bonds to the
maximum amount of hydrogen atoms possible
• These compounds are saturated with hydrogen atoms
– Include Alkanes (straight chains) & Cycloalkanes (carbon rings)
Saturated Hydrocarbons– Example:
Propane is classed as an alkane
– Molecular formula: C3H8
– Condensed structural formula: CH3CH2CH3
– The ends of the compound are CH3, whereas the middle is a CH2
Note: In a compound
carbon atoms must form 4 covalent bonds
hydrogen atoms must form 1 covalent bond
Propane
Saturated vs Unsaturated hydrocarbon compounds
Saturated Hydrocarbons– Example:
Cyclohexane is classed as a cycloalkane
– Molecular formula: C6H12
– Condensed structural formula: CH2CH2CH2CH2CH2CH2
– All carbon atoms are connected to two other carbon atoms,
so they are all CH2
• No CH3 ends present
– The compound has two less hydrogen atoms than an alkane with the same number of carbons• Due to lack of CH3 ends
Cyclohexane
Note: In a compound
carbon atoms must form 4 covalent bonds
hydrogen atoms must form 1 covalent bond
Saturated vs Unsaturated hydrocarbon compounds
Unsaturated Hydrocarbons– Unsaturated hydrocarbons have one or more double or triple
carbon to carbon bond(s)• Will also contain single carbon to carbon bonds
Saturated vs Unsaturated hydrocarbon compounds
– The carbon atoms in unsaturated hydrocarbons form bonds to less than the maximum amount of hydrogen atoms possible
• These compounds are not saturated with hydrogen atoms (unsaturated)– Due to the presence of double or triple carbon to carbon bonds
– Include Alkenes (straight chains) & Cycloalkenes (carbon rings)
Unsaturated Hydrocarbons– Unsaturated hydrocarbons have one or more double or triple
carbon to carbon bonds• Will also contain single carbon to carbon bonds
– Example:
Propene is classified as an alkene
– Molecular formula: C3H6
– Condensed structural formula: CH2CHCH3
– Extra carbon to carbon bond = two less hydrogens in the compound
Propene
Note: In a compound
carbon atoms must form 4 covalent bonds
hydrogen atoms must form 1 covalent bond
Saturated vs Unsaturated hydrocarbon compounds
Unsaturated Hydrocarbons– Example:
Cyclohexane is classed as a cycloalkene
– Molecular formula: C6H10
– Condensed structural formula: CHCHCH2CH2CH2CH2
– Has two less hydrogen atoms than an cycloalkane
with the same number of carbons• Extra carbon to carbon bond = two less hydrogens in the compound
Cyclohexene
Note: In a compound:
carbon atoms must form 4 covalent bonds
hydrogen atoms must form 1 covalent bond
Saturated vs Unsaturated hydrocarbon compounds
Classify the following compounds
as their an alkane, cycloalkane, alkene
or cycloalkene:
CH3CH2CHCH2
1.
2.
3.
4.
How is the covalent bonding within a
saturated hydrocarbon different from
the covalent bonding in an unsaturated hydrocarbon?
Is a saturated or unsaturated hydrocarbon likely to have
more hydrogens attached to the carbon atoms
in the compound? Why?
Does an unsaturated hydrocarbon compound contain any
single carbon to carbon bonds? Explain why/why not.
Key concept: Saturated and unsaturated hydrocarbons
Attempt Socrative questions: 5 to 8
Google Socrative and go to the student login
Room name:
City name followed by 1 or 2 (e.g. PERTH1)
1 for 1st session of the week and 2 for 2nd session of the week
Part 2: Drawing and interpreting organic compounds
• Representations of organic compounds
– Organic compounds can be represented in different ways:
• Molecular formula: shows only the number of each type of atom present in the compound
• Complete structural formula: shows the compete covalent bonding pattern of the compound
• Condensed structural formula: Specifies the structural formula using text and shows how many hydrogen atoms are connected to each of the carbon atoms in the compound
• Line bonding formula: Represents the bonds between carbon atoms as lines
– No chemical symbols are shown unless there is an atom type other than carbon and hydrogen in the compound
Part 2: Drawing and interpreting organic compounds
• Saturated vs unsaturated hydrocarbon compounds
– Saturated hydrocarbons contain only single carbon to carbon bonds and
contain the maximum number of hydrogen atoms attached to the carbon
atoms
– Alkanes and cycloalkane are saturated hydrocarbons
– Unsaturated hydrocarbons contain one or more double or triple carbon to
carbon bond, as well as other single carbon to carbon bonds
– Unsaturated hydrocarbons contain less than the maximum number of
hydrogen atoms attached to the carbon atoms, due to the presence of
double or triple carbon to carbon bonds
– Alkenes and cycloalkenes are unsaturated hydrocarbons
Part 3: Chemical reactivity of organic compounds
• Functional groups
• Stereoisomers
What are functional groups?– A functional group is a group of atoms within a compound that provides chemical reactivity
• The functional group is usually the part of the compound that is involved in chemical reactions
• All compounds with a particular functional group will behave similarly in chemical reactions
– To find a functional group within a compound,
look for atoms other than just carbon and hydrogen atoms
Functional Groups
Ethanol: present in alcoholic beverages
Alcohol Functional group
Why are functional groups useful?– Functional groups are key structural components of compounds that
determine the compounds properties and behaviour
– Functional groups are used to classify and name organic compounds
– A compound can contain zero, one or more than 100 functional groups
Carboxylicacid
Functional Groups
Amine
Amino acid: alanine
How are the different functional groups represented?– The simplified representation of a functional group is the atoms that make up
the function group attached to a place holder, represented by an R
• The R-group represents any possible combination of atoms
capable of attaching to the functional group
• Each functional group is made up of a different group of atoms
Functional Groups
Alcohol functional group present in a compound (Ethanol)
R OHAlcohol functional group
R represents any atom or group of atoms capable of attaching to the functional group
OH are the group of atoms within the alcohol functional group R
Functional group atoms
Functional groups can have one or two R-groups attached
– Single R-group functional groups are always found at the end of a compound
or at a branch point within a compound• Example: R-OH = alcohol functional group
– Two R-group functional groups are always found in the middle of a compound
and are often used to connect two compounds together• Example: R-O-R = ether functional group
Functional Groups
R OH1 R-group functional group: alcohol
R represents any atom or group of atoms capable of attaching to the functional group
OH is the group of atoms within the alcohol functional
group
R OR represents any atom or group of atoms capable of attaching to the functional group
O is the atom that makes up
the ether functional group
2 R-group functional group: ether
RR represents any atom or group of atoms capable of attaching to the functional group
R OH1 R-group functional group: alcohol
R represents any atom or group of atoms capable of attaching to the functional group
OH is the group of atoms within the alcohol functional
group
R OR represents any atom or group of atoms capable of attaching to the functional group
O is the atom that makes up
the ether alcohol functional group
2 R-group functional group: ether
RR represents any atom or group of atoms capable of attaching to the functional group
Functional group in the middle of a compound between two R-groupsR R
Stereoisomers are a group of two compounds that are very similar:
• The group of compounds has the same number of each type of atom present and the same
chemical bonding pattern
• Each of the two stereoisomer compounds are arranged differently in space
– The two different variations of the stereoisomer compounds
have different chemical properties
– Example:
• cis stereoisomer = both large CH3 groups are on the same side of the carbon to carbon double bond
• Trans stereoisomer = The large CH3 groups are on different sides of the carbon to carbon double bond
cis = same trans = different
Stereoisomers
Attempt Socrative questions: 9 to 10
Google Socrative and go to the student login
Room name:
City name followed by 1 or 2 (e.g. PERTH1)
1 for 1st session of the week and 2 for 2nd session of the week
Part 3: Chemical reactivity of organic compounds
• Functional groups– A functional group is a group of atoms within a compound that provides chemical
reactivity
– All compounds with a particular functional group will behave similarly in chemical reactions
– To find a functional group within a compound, look for atoms other than just carbon and hydrogen atoms
– A compound can contain zero, one or more than 100 functional groups
– The simplified representation of a functional group is the atoms that make up the function group attached to a place holder, represented by an R
– The R-group represents any possible combination of atoms capable of attaching to a functional group
– Single R-group functional groups are always found at the end of a compound or at a branch point within a compound
– Two R-group functional groups are always found in the middle of a compound
Part 3: Chemical reactivity of organic compounds
• Stereoisomers– Stereoisomers are a group of two compounds that are very similar, with each
compound having the same number of each type of atom present and the
same chemical bonding pattern
– The two stereoisomer compounds are arranged differently in space
– One type of stereoisomer pair is the cis stereoisomer and the trans
stereoisomer
Readings & Resources• Stoker, HS 2014, General, Organic and Biological Chemistry, 7th edn,
Brooks/Cole, Cengage Learning, Belmont, CA.
• Stoker, HS 2004, General, Organic and Biological Chemistry, 3rd edn, Houghton Mifflin, Boston, MA.
• Timberlake, KC 2014, General, organic, and biological chemistry: structures of life, 4th edn, Pearson, Boston, MA.
• Alberts, B, Johnson, A, Lewis, J, Raff, M, Roberts, K & Walter P 2008, Molecular biology of the cell, 5th edn, Garland Science, New York.
• Berg, JM, Tymoczko, JL & Stryer, L 2012, Biochemistry, 7th edn, W.H. Freeman, New York.
• Dominiczak, MH 2007, Flesh and bones of metabolism, Elsevier Mosby, Edinburgh.
• Tortora, GJ & Derrickson, B 2014, Principles of Anatomy and Physiology, 14th edn, John Wiley & Sons, Hoboken, NJ.
• Tortora, GJ & Grabowski, SR 2003, Principles of Anatomy and Physiology, 10th edn, John Wiley & Sons, New York, NY.