TOPIC 10

ORGANIC CHEMISTRY

10.1
FUNDAMENTALS OF ORGANIC CHEMISTRY
UNDERSTANDING/KEY IDEA
10.1.A
A homologous series is a series of
compounds of the same family, with
the same general formula, which
differ from each other by a common
structural unit.
HOMOLOGOUS SERIES
 Definition – family of organic compounds
which possesses certain common features.
 Successive members differ by a –CH2
group.
 Members of a series can be represented
by the same general formula.
 Members show a gradation in physical
properties.
 Members have similar chemical
properties.
MEMBERS DIFFER BY –CH2
 In a homologous series, as you change
from one member to the next, the molecular
mass increases by a fixed amount.
 This fixed amount is due to the addition of
successive –CH2 groups.
 When you go from propane to butane, what
changed?
 You added one carbon to the series along with
two hydrogen atoms.
 This is typical of each homologous series.
MEMBERS REPRESENTED
BY SAME GENERAL
FORMULA
 Alkanes and alkenes are represented by the
formulas CnH2n+2 and CnH2n respectively.
 A functional group is a small group of atoms
attached to a carbon atom giving the
compound characteristic properties.
 Functional groups are shown in the general
formulas.
 Alcohols are represented by CnH2n+1OH or
ROH where “R” is the parent hydrocarbon
abbreviation.
MEMBERS SHOW A
GRADATION OF PHYSICAL
PROPERTIES
 As successive members of a series
differ by a –CH2 group, they have
successively longer chains.
 There is a gradual trend in the change
of physical properties due to this
change in molar mass.
 Boiling point, density and viscosity are
physical properties with predictable
trends in homologous series.
MEMBERS SHOW SIMILAR
CHEMICAL PROPERTIES.
 Since members of a series have the
same functional group, their members
show similar chemical reactivity.
 If we know the characteristic reactions
of a functional group, we can predict
the properties of all members of a
series.
APPLICATION/SKILLS

Be able to explain the trends on

boiling points of members of a
homologous series.
BOILING POINT TRENDS

 The boiling point is affected by the

length of the carbon chain.
 Boiling point increases with increasing
carbon number.
 This is caused by the increased
number of temporary dipoles causing
stronger van der Waal’s forces between
molecules as their size increases.
 The first four alkanes are gases at room
temperature followed by the next four
alkanes existing as liquids at room temp.
 Methane has a boiling pt of -164°C and
octane 125°C.
 The increase is not linear, but steeper
near the beginning because the smaller
molecules are more affected by the
addition of a –CH2.
APPLICATION/SKILLS

Be able to distinguish between

empirical, molecular and
structural formulas.
EMPIRICAL FORMULA

 Definition – the simplest whole number

ratio of the atoms a compound contains.
 The formula can be derived from
percentage composition data obtained
from combustion analysis.
 It is limited in its use as it does not tell
us the actual number of atoms in the
molecule.
MOLECULAR FORMULA
 Definition – the actual number of atoms of each
element present in the compound and is a
multiple of the empirical formula.
 It does not show us how the atoms are
arranged in relation to each other and in space.
 Properties of a compound are determined by
not only the atoms, but by their arrangement in
space so the molecular formula is limited in its
value.
UNDERSTANDING/KEY IDEA
10.1.B
Structural formulas can be
represented in full and condensed
format.
STRUCTURAL FORMULA
 A full structural formula shows us every bond and
every atom.

H H

H-C–C–H

H H

 You must show all C’s and H’s and functional groups
in a structural formula or you will not receive credit.
Skeletal structures are not acceptable.
CONDENSED
STRUCTURAL FORMULA
 A condensed structural formula omits
bonds where they can be assumed
and groups atoms together.
CH3CH3 or CH3COOH
STEREOCHEMICAL
FORMULA
 Attempts to show the positions of
atoms in three dimensions.
 A bond sticking out of the front of the page
is represented by a solid triangular wedge.
 A bond sticking out of the back of the page
is dotted line.
 Four bonds are tetrahedral with bond
angles of 109.5°.
 Three bonds are trigonal planar with 120°.
UNDERSTANDING/KEY IDEA
10.1.C
Saturated compounds contain
single bonds only and unsaturated
compounds contain double and
triple bonds.
 GUIDANCE
Be able to apply the IUPAC rules in
nomenclature for the following:
1. non-cyclic alkanes and
halogenoalkanes up to halohexanes
2. alkenes up to hexene
3. alkynes up to hexyne
 GUIDANCE
4. Compounds up to 6 carbon
atoms containing only one of the
classes of functional groups:
alcohols, ethers, aldehydes,
halogenoalkanes, ketones, esters,
and carboxylic acids, amines,
amides, nitriles and arenes.
NOMENCLATURE:
IUPAC SYSTEM
 IUPAC (International Union of Pure and
Applied Chemistry) is an international,
non-governmental organization known
for its system of nomenclature now
recognized world wide.
 IUPAC uses the size of the molecules
and the functional groups present to
logically name compounds.
RULE 1: IDENTIFY THE
LONGEST STRAIGHT CHAIN
OF CARBON ATOMS
This longest chain is the “stem”. Memorize these:
 Meth – 1
 Eth – 2
 Prop – 3
 But – 4
 Pent – 5
 Hex – 6
 Hept – 7
 Oct – 8
 Non – 9
 Dec -10
RULE 2: IDENTIFY THE
FUNCTIONAL GROUP
 The functional group will be a specific
“suffix” which replaces the –ane in the
parent alkane.
UNDERSTANDING/KEY IDEA
10.1.D
Functional groups are the reactive
parts of molecules.
 GUIDANCE
Be able to distinguish between the
class names and functional group
names. For example, -OH, the
functional group is hydroxyl
whereas the class name is alcohol.
Functional Group: C-C

 Alkanes are single bonded carbon

chains.
 The suffix is –ane.
 Alkanes are saturated hydrocarbons.
 General formula: CnH2n+2
 Class – alkane
 Functional group – none
Functional Group: C=C
 Alkenes have a double bonded carbon within
the chain. Unsaturated.
 The suffix is –ene.
 The molecule is named by using the smallest
numbered carbon that is part of the double
bond. but-1-ene
 General formula: CnH2n
 Class – alkene
 Functional group – alkenyl
 Alkynes have a triple bonded carbon within the
chain. Unsaturated.
 The suffix is –yne.
 The molecule is named by using the smallest
numbered carbon that is part of the double
bond. but-1-yne
 General formula: CnH2n-2
 Class – alkyne
 Functional group – alkynyl
Functional Group: -OH
 Alcohols have the functional group –OH.
 The suffix is –anol.
 Examples are ethanol and propanol.
 The position of the functional group is shown by
a number between hyphens inserted before the
functional group ending.
 Propan-2-ol has the –OH group located on the 2nd
carbon of the series.
 General formula: CnH2n+1OH
 Class – alcohol
 Functional group – hydroxyl
Functional Group: R-O-R’
 Ethers have an oxygen in the chain between
two alkyl groups.
 The suffix is –oxyalkane.
 Examples are methoxyethane and ethoxypropane.
 General formula: R-O-R’
 Class – ether
 Functional group – ether
Functional Group: -C=O
H
 Aldehydes have the above functional group with a
double bonded oxygen on the carbon along with a
hydrogen.
 The carbon with the double bonded oxygen is used in
the stem name.
 The suffix or ending is –anal.
 C2H5CHO is propanal. (Notice the C in the CHO is
part of the carbons counted in the stem.)
 General formula: R-CHO
 Class – aldehyde
 Functional group –carbonyl
Functional Group: R-C=O
R’
 Ketones have a double bonded oxygen
on an interior carbon. The R and R’
represent the sides of the carbon chain.
 The ending or suffix is –anone.
 CH3COCH3 is propanone.
 General formula: R-CO-R’
 Class – ketone
 Functional group – carbonyl
Functional Group: -C=O
O-H
 Carboxylic Acids have a double bonded oxygen and an
–OH group attached to a carbon.
 The suffix is –anoic acid and the carbon attached to the
–OH and double bonded oxygen is counted in the stem
name.
 C2H5COOH is propanoic acid.
 CH3COOH is ethanoic acid. (We are used to seeing
HC2H3O2 as acetic acid, but it is the same as ethanoic
acid.)
 General formula: CnH2n+1COOH
 Class – carboxylic acid
 Functional group – carboxyl
Functional Group: -C=O
O-R
 Esters are organic salts where the alkyl group of the
alcohol has replaced the hydrogen of the carboxylic
acid.
 The suffix is –anoate.
 The name puts the alkyl group first followed by the
acid anion.
 C2H5COOCH3 is methyl propanoate.
 General formula: R-COO-R’
 Class – ester
 Functional group – ester
Functional Group: -NH2
 Amines have the functional group –NH2.
 The suffix is –anamine.
 Propanamine and butanamine are examples.
 Propanamine can also be named
1-aminopropane
 This is because –NH2 is also substituent group called
amino-.
 Class – amine
 Functional group – amine
Primary, Secondary and
Tertiary Amines
 Primary amines have one –NH2 group.
 The H’s can be substituted once or twice
with alkyl groups to form secondary or
tertiary amines.
 A secondary amine is C3H7NHCH3 which is
named N-methylpropanamine.
(The N is used in the name to signify that
methyl is attached to nitrogen.)
 C3H7N(CH3)2 N,N-dimethyl propanamine is a
tertiary amine.
Functional Group: -C=O
N-H
H
 Amides are derivatives of carboxylic acids
where the –OH is replaced by –NH2.
 The suffix is –anamide and the carbon
attached to the group is part of the stem.
 C2H5CONH2 is propanamide.
 Class – amide
 Functional group – carboxyamide
Primary, Secondary and
Tertiary amides
 Primary amides have an –NH2 group.
 Secondary amides have 1 alkyl group
bonded to the nitrogen.
 C2H5CONHCH3 is N-methylpropanamide.
(N-means the alkyl group is bonded to the
nitrogen.)
 Tertiary amides have 2 alkyl groups
bonded to the nitrogen.
 C2H5CON(CH3)2 is N,N-dimethyl propanamide.
 Nitriles have a carbon triple bonded to a
nitrogen.
 The suffix is –anenitrile.
 An example C2H5CN is propanenitrile. (Notice the
carbon bonded to the nitrogen is included in the
stem name.)
 Class – nitrile
 Functional group – nitrile
 As a substituent CN is called cyano
Functional group R-C-X
 Alkyl halides or haloneno alkane have a
carbon bonded to a halogen.
 Treat X as a substituent (where X is a
halide). F-fluoro, Cl-chloro, Br-bromo, I-iodo
 Class – Alkyl halides or haloneno alkane
 Functional group – bromo, fluoro, chloro,
iodo
 General formula: CnH2n+1X
Functional Group:
 Arenes are known as aromatic
compounds and contain the benzene
ring.
 The suffix is –benzene.
 An example would be methyl benzene.
 Class – arene
 Functional group – phenyl
UNDERSTANDING/KEY IDEA
10.1.E
Benzene is an aromatic, unsaturated
hydrocarbon.
APPLICATION/SKILLS

Be able to discuss the structure of

benzene using physical and
chemical evidence.
 Benzene has 3 alternating double bonded
carbons.
 It has a high degree of unsaturation.
 It has no isomers.
 It does not readily undergo addition
reactions expected of unsaturated
compounds.
 www.chemwiki.ucdavis.edu

 The first model for benzene was suggested by

Kekule in 1865 which suggested the cyclic
arrangement of the carbons with alternating
double bonds.
 This model explained some of the known
properties of benzene such as no isomers but
it did not explain the low reactivity.
 Advances in technology provided data to
develop the current model of the
benzene structure.

www.essentialchemicalindustry.org
 Each of the six carbon atoms is sp2
hybridized forming 3 sigma bonds with
angles of 120, making a planar shape.
 This leaves one unhybridized p electron
on each carbon atom with its dumb-bell
shape perpendicular to the plane of the
ring.
 The p orbitals effectively overlap in both
directions spreading themselves out evenly to
be shared by all 6 carbon atoms.
 This forms a delocalized pi electron cloud in
which electron density is concentrated in two
donut-shaped rings above and below the plane
of the ring.
 This very stable arrangement lowers the
internal energy of the molecule.
www.en.wikipedia.org
MORE ON BENZENE

 All carbon bonds are equal and intermediate

in length between single and double bonds.
 The delocalized structure is more stable
than the Kekule structure by about
152kJ/mol.
 Benzene more likely undergoes substitution
reactions rather than addition reactions.
RULE 3: IDENTIFY THE SIDE
CHAINS OR SUBSTITUENT
GROUPS
 Substituent groups are given as the first part
of the name or are the prefix of the name.
 Common substituents are: methyl-, ethyl-
propyl-, flouro- (-F), chloro- (-Cl), bromo- (-
Br), iodo- (-I), and amino- (NH2).
 Note that –NH2 can be a suffix or a prefix.
Usually, when it is the only functional group, it will
be the suffix. If there are 2 or more functional
groups, it will be a prefix as in amino acids.
 The position of the substituent group is given
by a number followed by a hyphen in front of
its name showing the carbon atom to which it
is attached.
 If there are more than one substituent
group of the same kind, use the prefixes
di-, tri-, tetra- before the name.
 Always number the groups from the
shortest end of the parent carbon chain.
 If there is more than one type of
substituent group, they are put in
alphabetical order.
UNDERSTANDING/KEY IDEA
10.1.F
Structural isomers are compounds
with the same molecular formula but
a different arrangement of atoms.
 Remember that the molecular formula only
shows us the atoms present. It does not
show us how they are arranged in space.
 Structural isomers have the same molecular
formula but different arrangements of atoms.
 Each isomer is a distinct compound having
unique chemical and physical properties.
 The number of isomers increases with
increasing molecular formulas.
APPLICATION/SKILLS

Be able to use IUPAC rules to name

straight-chain and branched
isomers through hexane, hexene
and hexyne.
 Methane, ethane and propane only have
1 structure.
 Butane, C4H6 has two isomers.
 Pentane, C5H12 has three isomers.
 Hexane, C6H14 has five isomers.
 You must be able to draw all of the above
structures.
 You must be able to name each of the
isomers for butane, pentane and hexane.
 Draw all of the structures and name each
of them for practice and to study.
 Ethene and propene have only one
structure.
 Butene, C4H8 has 2 isomers.
 Pentene, C5H10 has 2 isomers.
 Hexene, C6H12 has 3 isomers.
 You must be able to correctly draw and
name the isomers for butene, pentene
and hexene.
 Ethyne and propyne have only one
structure.
 Butyne, C4H6 has 2 isomers.
 Pentyne, C5H8 has 2 isomers.
 Hexyne, C6H10 has 3 isomers.
 You must be able to correctly draw and
name the isomers for butyne, pentyne
and hexyne.
APPLICATION/SKILLS

Be able to identify primary,

secondary and tertiary carbon
atoms in halogenoalkanes and
alcohols.
(Amines and amides too –
discussed earlier)
CLASSES OF COMPOUNDS

 A primary carbon atom is attached to the

functional group and at least 2 other hydrogen
atoms.
 These are known as primary molecules.
 C2H5OH, ethanol is a primary alcohol.
 A secondary carbon atom is attached to the
functional group, one hydrogen and 2 alkyl
groups. (It is in the middle of a carbon chain.)
 CH3CH(OH)CH3, propan-2-ol is a secondary
alcohol.
 A tertiary carbon atom is attached to the
functional group and three alkyl groups so it has
no hydrogen atoms.
 C(CH3)3OH, 2-methylpropan-2-ol is a tertiary alcohol.
 CH3CH2Br, bromoethane is primary.
 CH3CHBrCH2CH2, 2-bromobutane is secondary.
 (CH3)3CBr is tertiary.
TRENDS IN PHYSICAL
PROPERTIES
 Discuss volatility and solubility in
water of compounds containing
the functional groups: alcohol,
aldehyde, ketone, carboxylic acid
and halide.
MORE PHYSICAL
PROPERTY TRENDS
 Both the size of the hydrocarbon skeleton
and the functional group influence the
physical properties of a compound.
VOLATILITY
 This is a measure of how easily a substance
changes to a gaseous state.
 High volatility means the substance has a low
boiling point.
 Volatility means overcoming the intermolecular
forces or forces between molecules.
 The stronger the intermolecular forces, the
higher the boiling point.
VOLATILITY – 2 FACTORS

 Influence of carbon chain

 The longer the straight chain, the higher the
London dispersion forces so the higher
boiling point.
 Branched chain hydrocarbons cannot get in
as close to each other so the London
dispersion forces are not as strong.
 Basically, smaller chains have higher
volatility and branched chains of the same
hydrocarbon have higher volatility.
 Influence of functional group
 The nature of the functional group may influence the
strength of the intermolecular forces.
 Polar groups have higher boiling points and those
that exhibit hydrogen bonding are higher still.
 Comparisons are done with similar molar masses,
not similar numbers of carbon atoms.
 Compare ethanol, Mr = 46 and propane Mr = 44. Ethanol
has a boiling pt of 78°C and propane -42°C. Clearly the
hydrogen bonding in ethanol affects the volatility.
 SUMMARY OF VOLATILITY

Most Volatile Least Volatile

Alkane>halogenoalkane>aldehyde>ketone>alcohol>carboxylic acid
London Dispersion → dipole-dipole interaction →hydrogen bonding
increasing strength of molecular attraction →
increasing boiling point →
SOLUBILITY IN WATER

 Solubility is largely determined by the

extent to which the solute molecules are
able to interact and form hydrogen bonds
with water.
 Influence of hydrocarbon skeleton
 This part of the molecule is non-polar.
 It is unable to form hydrogen bonds with
water.
 Higher members of homologous series are
less soluble than lower members.
 Influence of the functional group
 Molecules with functional groups that form
hydrogen bonds with water are the alcohols,
carboxylic acids and the amines.
 The smaller members of these series are readily
soluble in water.
 Aldehydes, ketones, amides and esters are
less soluble.
 Halogenoalkanes, alkenes and alkanes are
insoluble.
 Citations

International Baccalaureate Organization. Chemistry Guide,

First assessment 2016. Updated 2015.
Brown, Catrin, and Mike Ford. Higher Level Chemistry. 2nd ed.
N.p.: Pearson Baccalaureate, 2014. Print.
ISBN 978 1 447 95975 5
eBook 978 1 447 95976 2

Most of the information found in this power point comes directly

from this textbook.

The power point has been made to directly complement the

Higher Level Chemistry textbook by Brown and Ford and is
used for direct instructional purposes only.