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*CHM 112*
CLASSES OF ORGANIC COMPOUNDS
What are Organic Compounds??
These are Compounds which mostly contains Carbon and
Hydrogen, and in few cases contain other elements such
as Oxygen, Nitrogen, Sulphur, Phosphorous, and
Halogens with the exception of their oxides.
Oxides such as carbonates, bicarbonates, cynide, CO2,
CO3 etc.
*Organic Carbons are otherwise known as Hydrocarbons*
They can be divided into two:
1. Aliphatic Hydrocarbons
2. Aromatic Hydrocarbons.
ALIPHATIC HYDROCARBONS: They are formed or results
from carbon being attached to another carbon in a
continuous chain. I.e *it is not ringed* eg the Alkane series.
Aliphatic hydrocarbons are also known as *Carbocyclic or
homocyclic compounds.They are opened chain
compounds. Eg Ethane, Propane, propyne.
Aliphatic hydrocarbons are named based on the number
of carbon atoms in the chain. The names follow the rules
of IUPAC nomenclature, which involves identifying the
longest continuous carbon chain and indicating the
position of substituents or functional groups.
Aliphatic hydrocarbons tend to have lower boiling points
than aromatic compounds of similar molecular weight.
This is because the weak van der Waals forces between
their molecules are easier to overcome.
CYCLIC COMPOUND: They are also known as *Ring
Compounds*. These are compounds containing Carbon in
a ring system. They can either be saturated or unsaturated.
Eg Cyclo hexane, Benzene etc.
HETEROCYCLIC COMPOUNDS These are Compounds
which have rings made of carbon atoms including one or
more different atoms known as *heterocyclic atoms* such
as Oxygen, Nitrogen, Sulphur, and Phosphorous.
Examples include, Pyrimidine (consists of 2 Nitrogens),
imidazole.
AROMATIC COMPOUNDS : They are Carboxy cyclic
compounds which contains one or more Benzoic ring and
are being triggered by Ultra Violet light.
Aromatic compounds contain a benzene ring structure and
exhibit unique stability due to resonance. They can have
various functional groups attached to the ring.
POLY NUCLEAR COMPOUNDS:These are compounds
containing more than one benzene rings on their system.
Eg Naphthalene, Anthracene. OR
Polynuclear compounds, also known as polycyclic
aromatic hydrocarbons, are organic compounds
composed of two or more benzene rings that are fused
together.
UNIQUE PROPERTIES OF CARBON
Since the number of Organic Compounds exceed 1million
and the number of carbon is Constantly increasing, no
other single element forms such a large number of
Compound, thus the existence of such a large number of
carbon is due to the unique properties which are described
below:
1. Tetravalency of Carbon.
2. Carbon can unite with another carbon by a double or
multiple bond.
3. There is existence of strong covalent bond between
carbon and other elements/atoms such as Nitrogen,
Oxygen, Sulphur, the Halogens and Phosphorous.
4. Carbon can unite with another carbon to form stable and
straight chain/stable branch chain compounds, eg
Pentane, Neo Pentane, Iso Pentane.
5. Carbon can unite with another Carbon and with other
element to form stable ring compounds eg Cyclobutane or
Cyclo alkanes.
6. Existence of a large number of isomers are present in
most carbon Compounds.
NOTE
1.Organic Carbons are *Hydrocarbons*. They can be
divided into Aliphatic hydrocarbon and Aromatic
Hydrocarbon
2. Aliphatic compounds are otherwise known as ACYCLIC
COMPOUND
3. CYCLIC compounds contain carbon in a ring system.
4. Aromatic Compound are carboxy cyclic Compounds
which contain one or more benzenoic ring and are being
triggered by Ultra violet light.
5. Poly nuclear compounds are compounds that contain
more than one benzene ring in their system.eg Napthalene,
Anthracene.
6.Aliphatic hydrocarbons are found in natural gas, crude oil,
and various fossil fuels. They are used as fuels, solvents,
and starting materials in the chemical industry.
7. Alkanes are generally less reactive than alkenes and
alkynes due to the absence of multiple bonds. Alkenes can
undergo addition reactions to form saturated compounds,
while alkynes can undergo addition reactions to form
alkenes.
8.Aromatic compounds exhibit resonance, where electrons
are delocalized within the benzene ring.
9.Aromaticity can be found in heterocyclic compounds,
where one or more carbon atoms in the ring are replaced
by hetero atoms like nitrogen, oxygen, or sulfur.
10. There are heterocyclic Polynuclear Compounds that
contain hetero-atoms like nitrogen, oxygen, or sulfur within
the fused ring structure. These compounds can have
unique properties and reactivities
~~*PEARL*
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Last week, we talked about Stereochemistry as the Chemistry (Study) of Stereoisomers
Stereoisomers as being isomers in which their atoms are connected in the same way but
differ in spatial arrangement Optical isomers are isomers containing Chirality Centers A
carbon atom bonded to four different other atoms or group of atoms is known as
chirality centre (also refer to as stereogenic centre, streocentre, asymmetric carbon)
we also mentioned that ..... A compound containing a chirality centre can exist as two
different isomers. The two isomers are non superimposable and are refer to as
enantiomers. A compound (molecule) containing chirality center is said to be chiral
provided it does not contain a plane of symmetry.
In addition, we discussed How to represent enantiomers using Perspective formula and
Fischer projection formula How to designate enantiomers as R or S enantiomers
Today we'll be looking at 1. Optical Activity 2. Geometrical Isomers
At the end of this class you are expected to be able to: i) describe the nature of plane-
polarized light
ii) define Optical rotation
iii) Identify dextrorotatory and levorotatory isomers
iv) discuss Polarimeter
v) calculate the specific rotation of a compound, given the relevant experimental data.
vi) define Racemic Mixture
vii) define and explain the lack of optical activity of racemic mixtures
viii) define and determine Optical Purity
ix) determine the percent composition of an enantiomeric mixture from polarimetry
data and specific rotation formula x) define, discuss and identify Geometrical isomers
xi) draw structural formulas that distinguish between cis and trans molecules.
xii) designate geometric isomers as E or Z isomers
Key terms to be encountered in this class
analyzer
dextrorotatory
levorotatory
optically active
plane-polarized light
polarimeter
polarizer
specific rotation,
[α] Racemic mixture
OPTICAL ROTATION
Optical rotation is a phenomenon observed when a molecule rotates the plane of
polarization. Enantiomers are the same in all respect physically i.e. same boiling points,
melting points, solubilities etc. The only exception are those properties that depends on
how group bonded to chirality center are arranged in space. One of such properties that
make a difference is the way they interact with polarized light. (Polarized light is
light that is reflected or transmitted through certain media so that all vibrations are
restricted to a single plane.) Compounds containing chirality center i.e chiral compound
rotates the plane of polarization Such compound that rotates the plane of polarization
are said to be optically active
An optically active compound that rotates the plane of polarization in a clockwise
direction is called dextrorotatory and indicated by (+). On the other hand an optically
active compound that rotates the plane of polarization in a counter clockwise direction
is said to be levorotatory and is indicated by (-) Dextro and levo are Latin prefixes for “to
the right” and “to the left” respectively
Note: a) (+) and (-) are symbols indicating the direction in which an optically active
compound rotates plane polarized light b) Whereas R and S indicate the arrangement of
the group about a chirality center, they are not synonymous. c) Some compound with
the R configuration are (+) while some are (-).
Polarimeter
Polarimeter is an instrument that is used to measure the amount that an optically
active compound rotates the plane of polarized light. It determine the angle through
which plane-polarized light has been rotated by a given sample. An analyzer is the
component of a polarimeter that allows the angle of rotation of plane-polarized light to
be determined.
Specific Rotation
The specific rotation of a compound is “the number of degree of rotation caused by a
solution of 1.0 g of the compound per mL of solution in a sample tube 1.0 dm long at a
specified temperature and wavelength”. Specific rotation can be calculated from the
following formula. (Attached) Specific rotations are normally measured at 20°C, and this
property may be indicated by the symbol [α]. Sometimes the solvent is specified in
parentheses behind the specific rotation value, for example, [α] = +12 (chloroform).
In response to the following Question:
Good morning sir I have a question The 2nd part where you talked about dextrorotary
and Levoratory and you said that R isn't always + and S isn't always - . I just wanted to
ask that if I want to determine if it is dextrorotary or levorotatory does that mean it
should only be rotated once and the atom with the lowest atomic mass doesn't always
have to be at the back as in the right part of the example.
Answer: Let me clarify that: 1. Assigning an enantiomer as R or S can be achieved by
looking at the structure of the compound 2. But for dextrorotatory or levorotatory, It
has to be determine by carrying out an experiment, i.e. you'll need to run your sample in
a polarimeter So Assigning R or S is quite different from determining whether a
compound is Dextro or Levo!
In continuation of our lecture......
Worked example: The observed rotation of 2.0 g of a compound in 10 mL of solution in
a polarimeter tube 25 cm long is + 134o. What is the specific rotation of the compound?
Class work
A sample with a concentration of 0.3 g/mL was placed in a cell with a length of 5 cm.
The resulting rotation at the sodium D line was +1.52°. What is the Specific rotation [α]?
Racemic Mixture
A mixture of equal amount of a pair of enantiomers is called a racemic mixture, a
racemic modification or a racemate. Racemic mixtures are optically in active and are
indicated as (±). For example (±) -2- bromobutane contains the (+) and the (-) –
enantiomers in equal amount.
Optical Purity
Optical purity or enantiomeric excess is the ratio of the observed specific rotation of a
compound to the specific rotation of the pure enantiomer of that compound. The
"optical purity" is a comparison of the optical rotation of a pure sample of unknown
stereochemistry versus the optical rotation of a sample of pure enantiomer. Optical
purity tells us how much of each enantiomer is present in an isolated or prepared
compound. It is expressed as a percentage. An enantiomerically pure sample means
there is one enantiomer present. If a sample of an optically active compound has an
observed specific rotation of Oo, then the sample contains a racemic mixture. If the
sample only rotates plane-polarized light half as much as expected, the optical purity is
50%.
If however the observed specific rotation deviates from the value of a pure enantiomer,
then the sample contains mixture of the enantiomer in an unequal proportion. Optical
purity (enantiomeric excess) can be determined mathematically as (Attached)
Because R and S enantiomers have equal but opposite optical activity, it naturally
follows that a 50:50 racemic mixture of two enantiomers will have no observable optical
activity
If we know the specific rotation for a chiral molecule, we can easily calculate the ratio of
enantiomers present in a mixture of two enantiomers, based on its measured optical
activity. When a mixture contains more of one enantiomer than the other, chemists
often use the concept of enantiomeric excess (ee) to quantify the difference.
Enantiomeric excess can be expressed as: (attached) For example, a mixture containing
60% R enantiomer (and 40% S enantiomer) has a 20% enantiomeric excess of R: i.e.
((60−50)×100)/50=20%
Exercises: 1.
The specific rotation of (S)-carvone is (+)61°. The optical rotation of a sample of a
mixture of R and S carvone is measured as (-)23°.
(a) Which enantiomer is in excess, and what is its ee?
(b) What are the percentages of (R)- and (S)-carvone in the sample?
2. The specific rotation of (S)-(+)-2-bromobutane is +23.1o. A sample of 2-bromobutane
has an observed specific rotation of +9.2o, what is its optical purity.
3. A mixture contains 3g of (+)-2-bromobutane and 2g of (–)-2-bromobutane. What is
the rotation of the mixture, given that (+)-2-bromobutane has a specific rotation of
+23.1°.
Exercise Draw the cis and trans isomers for the following compounds:
a. 1-ethyl-3-methylcyclobutane
b. 1-bromo-4-chlorocyclohexane
c. 2-methyl-3-heptene
d. 1,3-dibromocyclobutane
E – Z systems of designating geometric isomers As long as each of the carbons of an
alkene is bonded to only one substituent, we can use the terms cis and trans to
designate the structure of the alkene. If the hydrogens are on the same side of the
double bond, it is the cis isomer; if they are on opposite sides of the double bond, it is
the trans isomer. If the alkene is tri or tetra substituted the use of cis and trans becomes
meaningless. since we do not know which two of the three groups are being described If
you have a C=C bond, with a methyl group and a bromine on one carbon, and an ethyl
group on the other, it is neither trans nor cis, since it is not clear whether the ethyl
group is trans to the bromine or the methyl
This is addressed with a more advanced E/Z nomenclature.
The IUPAC system for naming alkene isomers, called the E-Z system, is based on the same "priority
rules" as R-S system which allow you to rank any groups.
The priority rules are often called the Cahn-Ingold-Prelog.
The rule works as follows: Each carbon in the pi bond is attached to two substituents.
For each carbon, these two substituents are ranked (1 or 2) according to the atomic numbers of the
atom directly attached to the carbon. (e.g. Cl > F ) (using the CIP priority rules)
If both substituents ranked 1 are on the same side of the pi bond, the bond is given the
descriptor Z (short for German Zusammen, which means “together”).
If both substituents ranked 1 are on the opposite side of the pi bond, the bond is given the
descriptor E (short for German Entgegen, which means “opposite”).
Breaking Ties
If you encounter a tie while assigning priority, you'll need to break the tie. For instance,
in the attached alkene one of the carbons of the alkene is attached to two carbon
atoms.
So how do we determine priorities in this case. How do we break ties?
Exercise
Can you easily translate cis- and trans- into (Z)- and (E)-? You might think that for
simple cases, cis- will just convert into (Z)- and trans- into (E)-.
For example, 1,2-dichloroethene and but-2-ene cases. But it doesn't always work!
Consider this relatively uncomplicated molecule. (Attached)
This is clearly a cis- isomer.
It has two CH3 groups on the same side of the double bond.
But work out the priorities on the right-hand end of the double bond.
The two directly attached atoms are carbon and bromine.
Bromine has the higher atomic number and so has the higher priority on that end.
At the other end, the CH3 group has the higher priority.
That means that the two higher priority groups are on opposite sides of the
double bond, and so this is an (E)- isomer - NOT a (Z)-.
Never assume that you can convert directly from one of these systems into the
other.
The only safe thing to do is to start from scratch in each case.
It Doesn’t matter that the two systems will sometimes give different results?
The purpose of both systems is to enable you to decode a name and write a correct
Formula. Properly used, both systems will do this for you – although the cis-trans
system will only work for very straightforward molecules.
