Porg Lec Midterms

OUR LADY OF FATIMA
UNIVERSITY Types of Nomenclature

COLLEGE OF PHARMACY
• Systematic Name
Hydrocarbons: – Composed wholly or especially coined or selected syllables
– Refers to the structure of compounds
Nomenclature • Trivial Name
PHARMACEUTICAL – A name no part of which is used in a systematic sense
– Refers to compounds independent of structure and
ORGANIC CHEMISTRY sometimes given before the structure is known
PORG111 • Semisynthetic-Semitrivial Name
– A name of which only a part is used in a systematic sense
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Classification of Hydrocarbons
• All organic compounds may be divided into
two broad classes based upon the pattern
of chain of carbon atoms.
–Open-chain or Aliphatic compounds
–Closed-chain or cyclic compounds
• Alicyclic compounds
• Aromatic compounds
Aliphatic Hydrocarbons Aliphatic Hydrocarbons

• This class includes all hydrocarbons (saturated – On the other hand, unsaturated compounds contain
a double (–C = C–) or a triple (–C ≡ C–) bond between
and unsaturated) and their derivatives which
two carbon atoms.
have open-chain structures.
– Saturated hydrocarbons are those which contain single
bonds between all carbon atoms such as
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Cyclic Hydrocarbons Alicyclic Hydrocarbons
• These compounds have atleast one ring (cyclic) • This group includes saturated and
system. These are further divided into two unsaturated cyclic hydrocarbons which
subclasses: homocyclic and heterocyclic based on resemble with the aliphatic hydrocarbons in
the atoms present in the ring. They are called properties. Some examples are given below:
homocyclic or carbocyclic when the ring is formed
by carbon atoms only.
• Homocyclic (carbocyclic) compounds may again

be divided into two groups namely alicyclic and
aromatic compounds.
Aromatic Homologous Series of Hydrocarbons

• The group of homocyclic compounds having
special set of properties are called aromatic
compounds. They also have characteristic
smell or aroma and hence called aromatic.
– These include aromatic hydrocarbons and their
derivatives are examples of such compounds are as
follows :
Nomenclature of Organic Nomenclature of Organic

Compounds Compounds
• In order to bring uniformity and rationality in naming the • IUPAC nomenclature is based on naming
organic compounds throughout the world, International
Union of Chemistry (in 1958) came out with a system of molecule’s longest chain of carbons
nomenclature later known as IUPAC (International Union connected by single bonds either in chain or
of Pure and Applied Chemistry) system.
in ring
• The purpose of the IUPAC system of nomenclature is to
establish an international standard of naming • Multiple bonds other than C and H, are
compounds to facilitate communication. indicated by prefixes or suffixes according to
• The goal of the system is to give each structure a unique
and unambigous name, and to complete each name with specific set of priorities.
a unique and unambigous structure.
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IUPAC Nomenclature of IUPAC Nomenclature of
Aliphatic Hydrocarbons Aliphatic Hydrocarbons
• ROOT WORD -It indicates the number of carbon atoms SUFFIX - It is again divided into two types.
in the longest possible continuous carbon chain also
i. Primary suffix: It is used to indicate the
known as parent chain chosen by a set of rules. The
root words used for different length of carbon chain
degree of saturation or unsaturation in the
are shown below. main chain. It is added immediately after the
root word.
ii. Secondary suffix: It is used to indicate the
main functional group in the organic
compound and is added immediately after
the 1o suffix.

Aliphatic Hydrocarbons Acyclic Hydrocarbons
LOCANT • In branched chain hydrocarbons, one or more alkyl groups are
• Denotes the numeral or letter that indicates the position of present as side chain attached to the main straight chain of
an atom or group in a molecule. carbon atoms.
• The carbon atoms of the side chain constitute alkyl groups.
• Numerals
• These alkyl groups are written as prefixes in the IUPAC name.
– Numeral is a locant when it indicates the position of a
substituents or bond in a structure • An alkyl group is obtained from an alkane by removing one
hydrogen atom.
– separated by commas (eg. 1,2,5,6-tetrabromocyclohexane), no
space after the comma or colon • Since the general formula of alkane is CnH2n+2, the general
formula of alkyl group is CnH2n+1.
– sets of numerals are joined by hypen
• The alkyl groups are generally represented by R– and named by
– arranged in ascending order
replacing the suffix –ane of the corresponding alkane by –yl.
• place as early in a name as to not cause confusion
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Acyclic Hydrocarbons Acyclic Hydrocarbons
Rule 1. Longest chain Rule: Rule 1. Longest chain Rule:
• According to this rule, the longest possible chain
of carbon atoms is considered and the compound
is named as the derivative of the corresponding
alkane.
• If some multiple bond is present, the selected
chain must contain the carbon atoms of the
multiple bond. The number of carbon atoms in
the selected chain determines the word root and
the saturation or unsaturation will determine the
suffix.
IUPAC NAME (International Union of

Pure and Applied Chemistry)
Locant/ Suffix/
Prefix – Root – Ending
Denotes number longest functional class and
identify carbon attached groups chain

Rule 1. Longest chain Rule: Rule 1. Longest chain Rule:
• If two equally long chains are possible, the chain with
maximum number of side chains is selected as
the main chain .
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Rule 2. Lowest number or lowest sum rule: Rule 2. Lowest number or lowest sum rule:
• The longest carbon chain is numbered from one a) The substituted carbon atoms have the lowest
end to another and the positions of the side chain possible numbers.
are indicated by the number of carbon atoms to
which these are attached. The numbering is done
in such a way that :

Rule 2. Lowest number or lowest sum rule: Rule 3:
b) The sum of numbers used to indicate the If some multiple bond is present in the chain the
positions of various alkyl groups must be the carbon atoms involved in the multiple bond should
lowest. get the lowest possible numbers.

Rule 4: Naming of compounds with one alkyl group as Rule 5: Naming the same alkyl groups at different
the substituent (side chain) positions or more than one alkyl groups
• If the compound contains more than one identical alkyl
groups, their positions are indicated separately and the
prefixes di (for two), tri (for three) etc. are attached to
the name of the substituents.
• The positions of the substituents are separated by
commas (,).
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Rule 5: Naming the same alkyl groups at different Rule 6: Naming different alkyl substituents
positions or more than one alkyl groups • If there are different alkyl substituents present in
the compound, their names are written in the
alphabetical order. However, the prefixes di, tri,
etc. are not considered in deciding the
alphabetical order

Acyclic Hydrocarbons Cyclic Hydrocarbons
Rule 6: Naming different alkyl substituents • Alicyclic compounds have closed chain i.e.
cyclic structures, hence their names are
derived by putting prefix ‘cyclo’ before the
word root.
• The suffix ane, ene or yne are written
according to the saturation or unsaturation in
the ring structure.
OUR LADY OF
FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PORG111

Cyclic Hydrocarbons Cyclic Hydrocarbons
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Alicyclic Compounds: Aromatic Compounds
• If an alkyl substituent is present, it is indicated by the • The most important members of this class are benzene and
appropriate prefix and its position is indicated by numbering the its derivatives.
carbon atoms of the ring in such a way so as to assign the least • For naming an alkyl substituted benzene, the carbon atoms
possible number to the of benzene are numbered from 1 to 6 by giving the lowest
possible number to the position of the side chain or
substituent.
substituent.
IUPAC Nomenclature of
Cyclic Hydrocarbons IUPAC Nomenclature of
Aromatic Compounds Cyclic Hydrocarbons
Aromatic Compounds :
• Benzene forms only one monosubstituted
derivatives like methylbenzene or ethylbenzene .

Aromatic Compounds: • Common Parent Ring System
• However, it can form three disubstituted compounds
namely 1,2; 1,3 and 1, 4 derivatives.
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OUR LADY OF FATIMA IUPAC Nomenclature of
UNIVERSITY Cyclic Hydrocarbons
COLLEGE OF PHARMACY
• Alicyclic compounds have closed chain i.e.
Hydrocarbons: cyclic structures, hence their names are
derived by putting prefix ‘cyclo’ before the
Nomenclature word root.
PHARMACEUTICAL
• The suffix ane, ene or yne are written
ORGANIC CHEMISTRY
according to the saturation or unsaturation in
PORG111 the ring structure.

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Alicyclic Compounds: Aromatic Compounds
• If an alkyl substituent is present, it is indicated by the • The most important members of this class are benzene
appropriate prefix and its position is indicated by numbering and its derivatives.
the carbon atoms of the ring in such a way so as to assign the
least possible number to the substituent. • For naming an alkyl substituted benzene, the carbon
atoms of benzene are numbered from 1 to 6 by giving
the lowest possible number to the position of the side
chain or substituent.

Aromatic Compounds Aromatic Compounds:
• Benzene forms only one monosubstituted derivatives like
methylbenzene or ethylbenzene.

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The use of Phenyl and Benzyl The use of Phenyl and Benzyl
in Nomenclature in Nomenclature
• If the alkyl group attached to the benzene contains seven or • The benzyl group, similar to the phenyl group
more carbons the compounds is named as
and can be written as C6H5CH2-R, PhCH2-R, or
Bn-R.
– For example, a chlorine attached to a benzyl group
would simply be called benzyl chloride, whereas
an OH group attached to a benzyl group would
a phenyl
simply be called benzyl alcohol.
substituted alkane.
The use of Phenyl and Benzyl IUPAC Nomenclature of

in Nomenclature Cyclic Hydrocarbons
Aromatic Compounds:
• However, it can form three disubstituted compounds
namely 1,2; 1,3 and 1, 4 derivatives.

If any do appear then the compound is not named as a the compound is named as such:
benzene but with a different parent name. These substituents in alphabetical order + benzene.Remember
compounds are named as such: if two of the same substituent appears then the prefix
substituent + Name of parent used before the substituent's name.
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• When three or more substituents are present the ortho, meta, • Common Parent Ring System
para positional prefixes become inadequate and a numbering system
for the ring
must
be applied.

Alkyl Halides Alkyl Halides
• The common names of alkyl halides consist of
two parts:
– the name of the alkyl group plus the stem of the
name of the halogen, with the ending -ide.
• The IUPAC system
– uses the name of the parent alkane with a prefix
indicating the halogen substituents, preceded by
number indicating the substituent’s location.
• The prefixes are fluoro-, chloro-, bromo-, and iodo-.
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OUR LADY OF FATIMA Learning Outcome:
UNIVERSITY
COLLEGE OF PHARMACY • At the end of this module, the student must
be able to:
– Demonstrate understanding of the physical and
chemical properties in relation to structure
Physical and Chemical Properties

PHARMACEUTICAL
ORGANIC CHEMISTRY
PORG111
2 OUR
1 LADY OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PORG111
Physical Property
• A property that does not affect the chemical
Intermolecular Forces
identity of a compound • The physical properties of molecules are in part
dependent on the type's of intermolecular forces (IMF)
• Can be observed and measured without changing present.
a compound’s composition of matter – Boiling points (BP) are also dependent on the mass of the
– Any substance that has mass and can occupy space molecule.
– Solubility, the ability to dissolve into a solvent is dependent
on IMFs.
• The strength of the interaction between molecules is
also dependent on the overall shape of the molecule.
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LADY OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PORG111 OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PORG111
Intermolecular Forces Hydrogen Bonding
Hydrogen bonding is a complex interaction that includes

There are 3 types of IMFs, by decreasing strength they are:
dipole-dipole, as well as orbital interactions and the transfer of
1) Hydrogen bonding electron density between molecules.
2) Dipole-dipole – These are the strongest of the IMFs and range from 5 –
25 kJ/mol
3) Van der Waals or London Dispersion
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LADY OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PORG111 OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PORG111
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X-H ----:X-
Hydrogen Bonding Dipole-Dipole
Occur primarily between OH, NH and FH. The more EN the atom the
stronger the interaction. (The atom H is attached to usually has a lone pair
Dipole-dipole forces arise from the attraction of
of e-) oppositely charged atoms (other than H) in
Geometry: molecules. These molecules may have a
-
permanent dipole moment. Generally in organic
molecules they results from the presence of C-X
bonds where X is more electronegative that C.
– These are generally weaker than H-bonding, ranging
+
from about 5-10 kJ/mol.
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Dipole-Dipole Van der Waals

• Van der Waals or (London) dispersion forces arise
from the movement of electrons within a
molecule. This natural motion can produce an
uneven distribution of the electrons (polarization
of the distribution) resulting in a temporary
dipole moment in the molecule. This will induce
+-
the movement of electrons in adjacent molecules
producing a dipole moment in them.
– These “induced” dipole moments are very brief as
+ H 3C they disappear when the electrons move to new
N - locations within the molecule, so they forces are
very brief and weak, only 2-5 kJ/mol.
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UNIVERSITY – COLLEGE OF PHARMACY – PORG111 OUR LADY OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PORG111
Factors Affecting the Physical

Properties of Organic Compounds
Structural Effects on IMFs
– Structure of Functional Group
• The strength of the IMFs – Molecules having a polar functional group have a higher
depend on the amount of b.p. than others with a non-polar functional group of
contact between the similar molecular masses.
molecules, especially for
dispersion forces. Hence
the shape of the molecule
can affect the surface area
of contact, long thin
molecules have more
surface in contact than
spherical molecules.
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13 OUR 14 OUR LADY OF FATIMA
LADY OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PORG111 UNIVERSITY – COLLEGE OF PHARMACY – PORG111
Solvent polarity Length of Carbon Chains

• Molecules with higher molecular masses have Length of Carbon Chains
higher m.p., b.p. and density
• Molecules with branched chains
Higher molecular masses
 b.p. and density lower than its straightchain isomer
 Large molecular sizes
 Stronger London dispersion forces among
Straight-chain isomers have greater surface area in
molecules
contact with each other
 Greater attractive force among the molecules
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Length of Carbon Chains

• As a rule, larger molecules have higher boiling
(and melting) points.
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Solubility Solubility
• If the solvent is polar, like water, then a smaller
hydrocarbon component and/or more charged, • Any functional group that can
hydrogen bonding, and other polar groups will tend to donate a hydrogen bond to water
increase the solubility. (eg. alcohols, amines) will significantly contribute to water
solubility.
• The number of Carbons. More carbons means more of
a non-polar/hydrophobic character, and thus lower • Any functional group that can only accept a hydrogen bond
solubility in water. from water (eg. ketones, aldehydes, ethers) will have a
– Anything with a charged group (eg. ammonium, carboxylate, somewhat smaller but still significant effect on water
phosphate) is almost certainly water soluble, unless it has solubility.
large nonpolar group, in which case it will most likely be – Other groups that contribute to polarity (eg. alkyl halides, thiols
sulfides) will make a small contribution to water solubility.
soluble in the form of micelles, like a soap or detergent.
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OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PORG111 UNIVERSITY – COLLEGE OF PHARMACY – PORG111
Boiling Point and Melting Point Boiling Point and Melting Point
• Melting and boiling are processes in which
noncovalent interactions between identical
molecules in a pure sample are disrupted.
– The stronger the non-covalent interactions, the more
energy that is required, in the form of heat, to break
them apart.
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Boiling Point and Melting Point

• The boiling points of the compounds in any
homologous series increase as their
molecular weights increase because of the
increase in van der Waals forces.
– Branching in a compound lowers its boiling point
because it reduces the area of contact.
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Chemical Properties
Reaction Mechanism
• A chemical reaction occurs when one substance is
• Define as the detailed knowledge of the steps
converted into another substance(s).
involved in a process in which the reactant molecules
• A chemical reaction is accompanied by breaking of change into products.
some bonds and by making of some others. • Chemical reactions involve breaking of one or more of
the existing chemical bonds in reactant molecule(s)
and formation of new bonds leading to products.
• The breaking of a covalent bond is known as bond
fission.
• During bond breaking or bond fission, the two shared
electrons can be distributed equally or unequally
between the two bonded atoms.
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Heterolytic Fission
Homolytic Fission • The fission of a covalent bond involving unequal sharing of
The fission of a covalent bond with equal sharing of bonding electrons.
• This type of bond fission results in the formation of ions. The
ion which has a positive charge on the carbon atom, is known
bonding electrons. as the carbonium ion or a carbocation. On the other hand, an
ion with a negative charge on the carbon atom is known as
the carbanion.
• Free radicals are neutral but reactive species

having an unpaired electron and these can also
initiate a chemical reaction.
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Heterolytic Fission Types of Reactions in

Organic Compounds
• Substitution
– A substitution reaction involves the displacement of
• The charged species obtained by the one atom or group in a molecule by another atom or
heterolytic fission initiate chemical reactions group. Aliphatic compounds undergo nucleophilic
substitution reactions.
and they are classified as electrophiles and
– For example, a haloalkane can be converted to a wide
nucleophiles.
variety of compounds by replacing halogen atom (X)
– Electrophiles: An electrophile is an electron deficient species and it with different nucleophiles as shown below.
may be positively charged or neutral.
• Examples are H+ , AlCl3 , Br2 , Cl2 , Ag+ , CH3 +, BF3 etc.
– Nucleophiles : A nucleophile is negatively charged or
electron rich neutral species.
• Examples of nucleophiles are OH– , –NO2+ , H2O, :NH3 etc.
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Types of Reactions in
Organic Compounds
– Another type of substitution reaction which takes
place in an aromatic hydrocarbons. In this case, an
electrophilic reagent attacks the aromatic ring
because the latter is electron rich. The leaving group,
in this case, is always one of the hydrogen atom of
the ring.
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Types of Reactions in Types of Reactions in

Organic Compounds Organic Compounds
• Elimination • Addition
– An elimination reaction is characterized by the – Unsaturated hydrocarbons such as alkenes and
removal of a small molecule from adjacent carbon alkynes are extremely reactive towards a wide
atoms and the formation of a double bond. variety of reagents.
– The carbon-carbon double bond (–C=C–) of an
alkene contains two types of bonds. In alkynes,
three carbon-carbon bonds.
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Types of Reactions in
Organic Compounds
• Molecular Rearrangements
– proceeds with a fundamental change in the
hydrocarbon skeleton of the molecule. During this
reaction, an atom or group migrates from one
position to another.
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OUR LADY OF FATIMA Isomers
UNIVERSITY
COLLEGE OF PHARMACYCOLLEGE OF PHARMACY • Compounds having the same molecular
formula and same molecular weight but
Isomerism different structural formula, thus differ in
PHARMACEUTICAL physical and chemical properties.
ORGANIC CHEMISTRY
PORG111
• Structural Isomerism
•
AKA Constitutional Isomers
Compounds which have the same molecular
formula but differ in their structure are called
structural isomers.
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Structural Isomerism Chain Isomers

• These isomers differ in the chain of the carbon
atoms.
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Functional Isomers Functional Isomers
• These isomers differ in the type of functional • These isomers differ in the type of functional
group. group.
Positional Isomers Positional Isomers

• These isomers differ in the attachment of the • These isomers differ in the attachment of the
functional group to the chain at different functional group to the chain at different
positions. positions.
Metamers Metamers
• This type of isomerism arises due to the • Example: C4H10O can be represented as
presence of different alkyl chains on each side
of the functional group. ethoxyethane (C2H5OC2H5) and methoxypropane
• It is a rare type of isomerism and is generally (CH3OC3H7).
limited to molecules that contain a divalent
atom (such as sulfur or oxygen), surrounded by
alkyl groups.
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Tautomers Ring-chain Isomers
• isomer of the compound which only differs in the position of • one of the isomers has an open-chain structure whereas the
protons and electrons. other has a ring structure.
• It occurs via an intramolecular proton transfer. • A great example of this type of isomerism can be observed in
• An important example of this phenomenon is Ketoenol C3H6.
tautomerism.
Stereoisomers
• are isomers that have the same composition
(that is, the same parts) but that differ in the
orientation of those parts in space.
–Geometrical
–Optical
OUR LADY OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PORG111 OUR LADY OF

Geometrical Isomers Geometrical Isomers

• It is popularly known as cis-trans isomerism. • A cis- isomer is the one having identical groups
• These isomers have different spatial on same side of double bond.
arrangements of atoms in three-dimensional • A trans-isomer has identical groups on opposite
space. side.
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Optical Isomers Optical Isomers
• compounds having at least one carbon atom
joined to four different atoms or groups.
• Such a carbon atom is called asymmetric or
chiral carbon atom; and those which are not
chiral (do not have four different groups) are
called achiral.
NOTE: The wedge sign shows that the direction of the bonds is towards the
viewer and dotted line (.....) indicates backward direction of the bonds.
Optical Isomers Polarimeter

• have identical physical properties except optical
activity.
• They rotate the plane of plane polarized light in
opposite directions.
• The plane polarized light is defined as the light
that vibrates in one plane only.
• The rotation of the plane of polarized light is
called optical activity.
Optical Isomers Optical Isomers

• Compounds that rotate the plane of plane • Compounds that rotate the plane to the left
polarized light to the right (clockwise) are said (counterclockwise) are called levorotatory.
to be dextrorotatory. • This is denoted by placing 'l' or (-) before the
• The dextrorotatory is denoted by 'd' or (+) name of the compound.
before the name of the compound. • A mixture containing equal amounts of d- and l-
isomers is called a racemic mixture and is
optically inactive denoted by dl or ±.
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E-Z Notational System
E :higher ranked
substituents on opposite
sides C C
Z
lower lower
C C
Z
:higher ranked
substituents on same side
higher lower higher higher
lower higher
E
Importance of Chirality in Drugs

• Approximately 50% of marketed drugs are
chiral.
• The two enantiomers of a chiral drug may differ
significantly
– may have pharmacokinetic differences or
pharmacodynamic differences
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OUR LADY OF FATIMA Aromatic Hydrocarbons
UNIVERSITY
COLLEGE OF PHARMACY • Benzene (C6H6), was first isolated in 1825 by English
chemist Michael Faraday from the oily residues left
Aromatic Hydrocarbons from illuminating gas.
• In 1834 it was prepared from benzoic acid (C6H5CO2H),
PHARMACEUTICAL
a compound obtained by chemical degradation of
ORGANIC CHEMISTRY gum benzoin, the fragrant balsam exuded by a tree
PORG111 that grows on the island of Java,
Indonesia.
Aromatic Hydrocarbons Aromatic Hydrocarbons

• Thus benzene, toluene, and related hydrocarbons, • Benzene, C6H6, is the parent hydrocarbon of the
while not particularly pleasant-smelling themselves, especially stable compounds known as aromatic
were classified as aromatic because they were compounds.
obtained from fragrant substances. • The term aromatic thus came to mean any compound
• Joseph Loschmidt, an Austrian chemist, recognized in structurally derived from benzene.
1861 that most aromatic substances have formulas • These compounds are hydrocarbons that contain a
that can be derived from benzene by replacing one or benzene ring as a structural unit. In addition to benzene,
more hydrogens by other atoms or groups. other examples include toluene and naphthalene.
Aromatic Hydrocarbons Aromatic Hydrocarbons

• Physical Properties
– All arenes are either liquids or solids at room temperature; none are
gases.
– Aromatic hydrocarbons are insoluble in water.
– Benzene was once widely used as a solvent, but evidence of its
carcinogenic properties prompted its replacement by less hazardous
solvents.
• Sources
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Aromatic Hydrocarbons : Substitution
OUR LADY OF FATIMA UNIVERSITY COLLEGE OF PHARMACY
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Aromatic Hydrocarbons : Substitution Aromatic Hydrocarbons : Substitution
• The most common reactions of aromatic compounds
involve substitution of other a toms or groups for a ring
hydrogen on the aromatic unit.
• Most of these reactions are carried out at temperatures
between about 0°C and 50°C
OUR LADY OF FATIMA Learning Outcomes

UNIVERSITY
COLLEGE OF PHARMACY At the end of discussion, student should be
able to:
– Explain the physicochemical properties of aliphatic
Aliphatic Hydrocarbons hydrocarbons.
PHARMACEUTICAL – Write reaction mechanisms of Aliphatic & Alicyclic
Hydrocarbons.
ORGANIC CHEMISTRY – Draw the products of reactions of Aliphatic &
PORG111 Alicyclic Hydrocarbons.
– Enumerate Hydrocarbons of pharmaceutical
importance.
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Alkanes Alkanes
SOURCES
– The two most important natural
SOURCES
sources of alkanes are petroleum and natural – Propane is the major const itu ent of liquefied
gas. petrol eum gas (LPG), a domestic fuel.
• Petroleum is a complex liquid mixture of organic compounds – Butane is the gas of choice in some area s.
(alkanes or cycloalkanes).
• Natural gas, often found associated with petroleum deposits,
consists mainly of methane (about 80%) and ethane (5%
to 10%). OUR LADY OF FATIMA UNIVERSITY

– COLLEGE OF PHARMACY
– PORG111
Alkanes
PHYSICAL PROPERTIES
– insoluble in water
• This is because water molecules are polar,
whereas alkanes are nonpolar (all the C-C and Alkanes
PHYSICAL PROPERTIES
Number of carbons Physical State
– At room temperature, alkanes occur as gases,
C1-C4 Gas liquids and solids depending on the number of
carbons available in the compounds.
C-H bonds are nearly purely covalent).
Number of carbons Physical State
C1-C4 Gas
C5-C17 Liquid C5-C17 Liquid

≥C18 Solid wax ≥C18 Solid wax
Alkanes Alkanes
• The mutual insolubility of alkanes and water is used to REACTIONS
advantage by many plants. – All of the bonds in alkanes are single, covalent, and nonpolar. Hence
– Alkanes often constitute part of the protective coating on leaves and alkanes are relatively inert.
fruits. – Alkanes ordinarily do not react with most common acids, bases, or
• If you have ever polished an apple, you know that the skin, oxidizing and reducing agents.
• Because of this inertness, alkanes can be used as solvents for
or cuticle, contains waxes. Constituents of these waxes extraction or crystallization as well as for carrying out chemical
include the normal alkanes C27H56 and reactions of other substances.
C29H60. – However, alkanes do react with some reagents, such as
• The leaf wax of cabbage and broccoli is mainly n- molecular oxygen and the halogens.
C29H60, and the main alkane of tobacco leaves is
C31H64.
27
Alkanes : Oxidation and
Alkanes
Combustion
REACTIONS
• The most important use of alkanes is as fuel. With excess oxygen,
– Oxidation alkanes burn to form carbon dioxide and water.
• addition of O, removal of H
• the replacement of C-H bonds by C-O bonds
• These combustion reactions are the basis for the use of
– Halogenation hydrocarbons for heat (natural gas and heating oil) and for power
• one or more hydrogen atoms of the alkane are (gasoline).
replaced by halogen (X) atoms • An initiation step is required, usually ignition by a spark or flame.
Onceinitiated, the reaction proceeds spontaneously and
• X - F, Cl, Br, I
exothermically.
Alkanes : Oxidation and Alkanes : Halogenation

Combustion • When a mixture of an alkane and chlorine gas is stored at
low temperatures in the dark, no reaction occurs.
• If insufficient oxygen is available for complete combustion of a
• In sunlight or at high temperatures, however, an
hydrocarbon, partial oxidation may occur.
exothermic reaction occurs.
This reaction can be represented by the general equation:
Alkanes : Halogenation Alkanes : Halogenation

• Chlorination ofhydrocarbons isa substitution reaction
in which a chlorine atom is substituted for a hydrogen
atom.
28
Alkenes Alkenes
SOURCES SOURCES
– The simplest alkene,
ethene or ethylene, is a
plant hormone and an
important starting
material for the
manufacture of other
organic compound s.
– The alkene functional
group is found in sources
as varied as citrus
fruits, steroids, an d
insect pheromones.
OUR LADY OF FATIMA UNIVERSITY

– PORG111 OUR LADY OF FATIMA UNIVERSITY
– PORG111
9 of the top 50 organic chemicals; each is produced Produced from ethylene (ethene)
from ethylene.
CHEMICAL USES
solvent; constituent of cleaning preparations; in synthesis of
ethanol
esters
acetaldehyde slug killer, in the form of methaldehyde (CH3CHO)4
manufacture of vinyl acetate polymers, ethyl acetate solvent
acetic acid
and cellulose acetate polymers
ethylene oxide “cellosolves” (industrial solvents)
ethylene glycol anti-freeze; production of DacronOR
ethylene dichloride solvent; production of vinyl chloride
vinyl chloride manufacture of poly (vinyl chloride)—PVC
manufacture of poly (vinyl acetate) used in paint emulsions,
vinyl acetate
plywood adhesives and textiles
polyethylene “plastic” bags; toys; packaging
Alkenes
Produced from propylene (propene)
PHYSICAL PROPERTIES
– They are less dense than water and, being nonpolar,
CHEMICAL USES are not very soluble in water.
isopropyl alcohol rubbing alcohol; cosmetics; synthesis of acetone – As with alkenes, compounds with four or fewer
carbons are colorless gases, whereas higher homologs
propylene oxide manufacture of polyurethanes; polyesters
are volatile liquids.
cumene industrial preparation of phenol and acetone
molded articles (e.g., kitchenware); fibers for

polypropylene
indooroutdoor carpeting
29
Alkenes : Addition of Halogen

• In ALKANES, the most comm on reaction is • With ALKENES, on the other hand , the most
SUBSTITUTI ON expressed by the general equatio n. common reaction is ADDITION:

– PORG111
Alkenes : Addition of Halogen Alkenes : Hydration

• If an acid catalyst (e.g., H2SO4 or HCl) is present,
water adds to alkenes. It adds as H-OH, and the
products are alcohols.
Alkenes : Hydration Alkenes : Hydration

• If an acid catalyst is present, water adds to alkenes. It • If an acid catalyst is present, water adds to alkenes. It
adds as H-OH, and the products are alcohols. adds as H-OH, and the products are alcohols.
30
Alkenes : Addition of Alcohols Alkenes : Hydrogenation
• Alcohols react with alkenes in the same way that • The addition of hydrogen to alkenes in the presence
water does. Like the addition of water, the addition of a catalyst.
of an alcohol requires an acid catalyst .
• Catalytic hydrogenation of dou ble bonds is used

commercial ly to convert vegetable oils to
• The product of the reaction is an ether. margarine and other cooking fats.

– PORG111
Addition of Asymmetric Reagents

to Asymmetric Alkenes
Addition of Asymmetric Reagents to

Asymmetric Alkenes
31
Alkynes Alkynes
SOURCES SOURCES
– There are only a few naturally occurring alkynes . – There are only a few naturally occurring alkynes .

– PORG111
Alkynes
PHYSICAL PROPERTIES
– Alkenes and alkynes have physical properties similar to
those of alkanes.
• All are insoluble in water and all are soluble in solvents with low
polarity such as benzene and ether.
• They are less dense than water and, like other homologous
series, have boiling points that increase with increasing
molecular weight.
• An alkyne has a higher boiling point than an alkene
containing the same number of carbon atoms.
32
Alkynes Alkynes
REACTIONS REACTIONS
– Alkynes, like alkenes, undergo electrophilic addition reactions. – The addition reactions of alkynes, however, have a feature
– We will see that the same electrophilic reagents that add to that alkenes do not have: Because the product of the addition
alkenes also add to alkynes. of an electrophilic reagent to an alkyne is an alkene, a second
electrophilic addition reaction can occur.
– Though, alkynes are less reactive than alkenes in electrophilic
addition reactions.
HYDROCARBONS OF HYDROCARBONS OF
PHARMACEUTICAL IMPORTANCE PHARMACEUTICAL IMPORTANCE
Valproic acid Amobarbital Phencyclidine Ethosuximide
• used to treat seizure • sedative-hypnotic • also known as angel dust • used to control absence
disorders, mental/mood • dissociative hallucinogenic seizures (petit mal)
conditions (such as manic drug used for its mind -
phase of bipolar disorder) altering effects

– PORG111
HYDROCARBONS OF HYDROCARBONS Vinyl chloride

• manufacture of poly (vinyl
PHARMACEUTICAL OF chloride)—PVC
IMPORTANCE PHARMACEUTICAL
IMPORTANCE
Diethylstilbestrol
• a synthetic, nonsteroidal form of
estrogen
• well-known teratogen and
Secobarbital
• anaesthetic, carcinogen
anticonvulsant,
33
anxiolytic, sedative,
and hypnotic
HYDROCARBONS • Allylisopropylacetamide
acts as a suicide inactivator
HYDROCARBONS OF
OF of CYTOCHROME P450 by PHARMACEUTICAL
covalently binding to its
PHARMACEUTICAL heme moiety or IMPORTANCE
surrounding protein.
IMPORTANCE Fluroxene
• is a volatile, inhalational
Stilbene anesthetic, and was
• manufacture of dyes and optical
the first halogenated
brighteners, and also
hydrocarbon
as a phosphor (luminescence) and a
scintillator anesthetic to be
introduced.
HYDROCARBONS OF
PHARMACEUTICAL IMPORTANCE
Ponatinib Efavirenz
• manufacture of dyes and • acts as a suicide inactivator
optical brighteners, and also of CYTOCHROME P450 by
as a phosphor covalently binding to its
(luminescence) and a heme moiety or
scintillator surrounding protein.

– PORG111
34
OUR LADY OF FATIMA Alkyl Halides
UNIVERSITY
COLLEGE OF PHARMACY • Sources
– Chlorine- and bromine-containing natural products
Alkyl Halides have been isolated from various species that live in
the sea —sponges, mollusks, and other ocean
PHARMACEUTICAL creatures that adapted to their environment by
ORGANIC CHEMISTRY metabolizing inorganic chlorides and bromides that
are prevalent there.
PORG111

• Alkyl halides (RX, where R is an alkyl group and X is F, • Physical Properties
Cl, Br, or I) – The boiling points of ethyl halides
– Can be classified as primary, secondary, or tertiary according increase as the atomic number of the
to the degree of substitution at the carbon to which the
halogen increases.
halogen is attached.
– Fluorine is the least polarizable of the
halogens and iodine the most
polarizable.
• An increased polarizability is associated with stronger
intermolecular attractive forces of the London dispersion
type and therefore with an increased boiling point.
•
Physical Properties Multiple fluorine substitution is an
• Multiple halogen substitution tends to increase the boiling
exception, however:
point:
Alkyl Halide Boiling
Alkyl Halide Boiling
Point
Point •
CH3CH2F −32 °C
CH3Cl −24 °C
CH3CHF2 -25 °C
CH2Cl2 40 °C
CH3CF3 -47 °C
CHCl3 61 °C
CF3CF3 -78 °C
CCl4 77 °C
By reducing the molecular polarizability, multiple
fluorine substitution weakens the strength of dispersion
forces •between molecules.
35
1
Alkyl Halides:
Addition of Hydrogen Halide to Alkene

COLLEGE OF PHARMACY
36
Alkyl Halides Alkyl Halides: Alcohol
• Several naturally occurring halogen-containing
with Hydrogen Halide
substances have pharmaceutical applications. An
example is the antibiotic Chloramphenicol produced
by Streptomyces venezuelae.
37

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OUR LADY OF FATIMA

UNIVERSITY Types of Nomenclature

OUR LADY OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PORG111

OUR LADY OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PORG111

Aliphatic Hydrocarbons Aliphatic Hydrocarbons

• Homocyclic (carbocyclic) compounds may again

OUR LADY OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PORG111

Aromatic Homologous Series of Hydrocarbons

OUR LADY OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PORG111

Nomenclature of Organic Nomenclature of Organic

IUPAC Nomenclature of IUPAC Nomenclature of

IUPAC NAME (International Union of

IUPAC Nomenclature of IUPAC Nomenclature of

OUR LADY OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PORG111

IUPAC Nomenclature of IUPAC Nomenclature of

IUPAC Nomenclature of IUPAC Nomenclature of

IUPAC Nomenclature of IUPAC Nomenclature of

IUPAC Nomenclature of IUPAC Nomenclature of

OUR LADY OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PORG111

OUR LADY OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PORG111

IUPAC Nomenclature of IUPAC Nomenclature of

OUR LADY OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PORG111

IUPAC Nomenclature of IUPAC Nomenclature of

IUPAC Nomenclature of IUPAC Nomenclature of

IUPAC Nomenclature of IUPAC Nomenclature of

The use of Phenyl and Benzyl IUPAC Nomenclature of

IUPAC Nomenclature of IUPAC Nomenclature of

IUPAC Nomenclature of IUPAC Nomenclature of

Physical and Chemical Properties

3 OUR 4 OUR LADY

Intermolecular Forces Hydrogen Bonding

Hydrogen bonding is a complex interaction that includes

5 OUR 6 OUR LADY

from about 5-10 kJ/mol.

7 OUR LADY OF FATIMA 8

Dipole-Dipole Van der Waals

9 OUR LADY OF FATIMA 10

Factors Affecting the Physical

Solvent polarity Length of Carbon Chains

15 OUR LADY 16 OUR LADY OF FATIMA

Length of Carbon Chains

19 OUR LADY 20 OUR LADY OF FATIMA

21 OUR 22 OUR LADY OF FATIMA

Boiling Point and Melting Point

because it reduces the area of contact.

• Free radicals are neutral but reactive species

Heterolytic Fission Types of Reactions in

Types of Reactions in Types of Reactions in

OUR LADY OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PORG111

OUR LADY OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PORG111 OUR LADY OF

Structural Isomerism Chain Isomers

OUR LADY OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PORG111

OUR LADY OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PORG111

Positional Isomers Positional Isomers

OUR LADY OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PORG111 OUR LADY OF

Geometrical Isomers Geometrical Isomers

OUR LADY OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PORG111

Optical Isomers Polarimeter

OUR LADY OF FATIMA UNIVERSITY – COLLEGE OF PHARMACY – PORG111