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.