CH311 ORGANIC CHEMISTRY II

Mentor: Dr. Kabaso Kalebaila

Cell: 0964525969
Email: [email protected]
School of Mathematics and Natural Sciences
Chemistry Department
 References List
•Morrison R.T . Organic Chemistry, Sixth Edition, 1992, Saurah Printers, Delhi.

•Wade, L.G, Jr. Organic Chemistry, Fourth Edition, 1999, Prentice Hall, New
Jersey.

•Bruce P.Y, (2001). Organic Chemistry, 3rd Edition. Prentice Hall, Pearson
Edition, New Jersey.

•Kemp .W, (1991). Organic Spectroscopy, 3rd Edition, Palgrave Macmillan.

•Uppal et al. (2001), Chemistry engineering text book. Khanna Publishers.

•James A. Kent, (2000). Riegels Handbook of Industrial Chemistry. Springer/

Van Norstrand/ReinHold.

•On-line references: do due diligence to look for specific topics.

 A. Introduction to Organic Chemistry
Organic chemistry is the study of compounds containing carbon with the exception of
simple compounds e.g. carbonates (CO32-), carbon dioxide (CO2) and carbon monoxide
(CO). There are over 6 million known organic compounds; therefore it is important to
name them. Moreover, it is equally important to know how to classify organic compounds
based on the similarities in behavior. This similarity is based on whether there are single,
double or triple bonds between carbon atoms. Here guidelines and examples will help
students in the naming as well as drawing the structures of compounds you will come
across during this course. This section is subdivided into three units namely organic
nomenclature; classification of organic compounds by functional groups and determining
formula of a compound from analysis of elemental composition.

Natural Sources of Organic Compounds

Alkanes / Alkenes /
Alkynes / Aromatic
Crude oil or hydrocarbons
coal Fractional distillation /
destructive distillation
 Important Concepts: Uniqueness of Carbon
Ability to form four strong covalent bonds: Electronic configuration of
carbon (ground state) : 1s22s22p2

Ability to Catenate: Carbon atoms link together to form straight and

branched chains of various lengths as well as of different sizes
Catenation: is the ability of atoms in forming stable bonds with itself, hence
joining up into chains or rings

C – C > Si – Si > Ge – Ge > Sn – Sn

Ability to Form Multiple Bonds: carbon can form single (saturated) bonds,
double or triple (unsaturated) bonds with it self or other elements.
Single bond Double bond Triple bond

* X = halogens

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 Hydrocarbons
The simplest organic compounds are hydrocarbons: compounds
containing only carbon and hydrogen.
 The three main groups of hydrocarbons are:
-saturated hydrocarbons (alkanes): hydrocarbons with only single
bonds between the carbon atoms.
-unsaturated hydrocarbons that contain double bonds (alkenes) or
triple bonds (alkynes) between carbon atoms.
-aromatic hydrocarbons, hydrocarbons that contain a benzene ring (a
six-membered ring of carbon atoms with alternating single and double
carbon-carbon bonds.

CH
HC CH

HC CH
CH
 IUPAC Nomenclature: Naming Alkanes
Alkanes are saturated hydrocarbons having single C-C bonds and belong to the
homologous alkane series. A homologous series is a series of compounds with the same
general formula with similar chemical properties, varying by the length of a carbon chain.
For alkanes the general formula is CnH 2n+2

1) Find the longest carbon chain in the molecule. This will give you the base or root of the name
2) The prefix shows number of C atoms in the chain, the suffix (-ane) shows that there only
single C-C bonds i.e. a saturated hydrocarbons.
 IUPAC Nomenclature: Naming Alkenes
Alkenes: are unsaturated hydrocarbons having as least a double C=C bond and the general
formula for this series is CnH2n. Like alkanes, the prefix denotes number of C atoms in the chain,
the suffix (-ene) indicating presence of C=C bond. Location of the double bond is specified by
numbering the C in the longest chain i.e. the root. Then give the double bond the lowest possible
number i.e. the root chain must be numbered from the end nearest a double bond
IUPAC Nomenclature: Naming Alkynes
Alkynes: are unsaturated hydrocarbons having as least a triple CC bond and
the general formula for this homologous series is CnH2n-2.
Rules for naming alkynes are the same as for naming alkenes.
The suffix (-yne) denotes presence of a CC bond.
 IUPAC Nomenclature: Naming Branched Hydrocarbons
Naming Branched Alkanes and Alkyl Groups

a) When naming branched alkanes, first identify and name the longest continuous carbon
chain i.e. the root name.
b) Second, identify the branch, or branches. The branches are called alkyl groups.
c) The names of alkyl groups are the same as those of corresponding alkanes, but their
names end in -yl, instead of -ane. For example, a one carbon branch is called a methyl
group.
d) Alky groups never exist by themselves. In alkanes they are always attached to the root
chain.
CH 3

CH 3 CH 2 CH 2 CH 2 CH CH 3

6 5 4 3 2 1 

1 2 3 4 5 6 
For the above, the longest chain is 6 C so its hexane
And the branch occurs at the lowest possible number so the correct name
is 2-methyl hexane and not 5 –methyl hexane
 IUPAC Nomenclature: Naming Branched Hydrocarbons
Consider another example below. The longest continuous carbon chain has 6 carbons,
thus is hexane. The two fluorines (difluoro) are assigned positions on the hexane chain,
by numbering from the F that is closest to the end.
Thus, 2,5 difluorohexane is the correct name not 3,5-difluorohexane.

The correct name for the next compound is 1-bromo-3-chlorohexane.

The branches (Br and Cl) are named in alphabetical order.
It would be wrong to name this as 4-chloro-6-bromohexane, why?

Further readings and online resources

•http://authors.library.caltech.edu/25034/4/BPOCchapter3.pdf
•Amgad M., Rabie, et al. (2010) Organic Chemistry, Wikibooks.
https://en.wikibooks.org/wiki/Organic_Chemistry
•http://www.chemguide.co.uk/basicorg/conventions/names.html
 B. Classification of Organic Compounds-
Functional Groups
•Organic compounds are classified into families according to structural features.
•The physical and chemical behavior of family members is often predictable based on
their specific grouping of atoms called functional groups.
• Most organic chemistry involves functional groups that contain O, N, S, or P
•Each functional group is part of a larger molecule, and a molecule may have
more than one class of functional group present.
•A functional group undergoes the same reactions in every molecule that contains it.
•The chemistry of an organic molecule is primarily determined by the functional groups

What is the best way to classify

organic compounds?
By their functional groups.
A. Families of Organic Molecules: Functional Groups:
We learnt about alkanes, alkanes and alkynes. In fact, alkanes are
a family with the functional group being the (C-C single bond), alkenes
with the (-C=C-) double bond and alkynes
with the (-CC- triple bond).

The special functional groups in this unit are:

• Those with only single bonds & a carbon atom bonded to an

electronegative atom e.g.
- Alkyl halides have a carbon–halogen bond e.g. RC-Cl
- Alcohols have a carbon–oxygen bond e.g. R-C-OH
- Amines have a carbon–nitrogen bond e.g. R-C-N-

• Those which contain a carbon–oxygen double bond:

- Aldehydes
- Ketone
- Carboxylic acid
- Ester and Amides
A. Families of Organic Molecules: Functional Groups:
 Alkyl halides:
•Alkyl halides have the general formula of RX (R-X) in which R is an alkyl or
aryl (aromatic) group i.e. a hydrogen is replaced by a halogen ion
i.e. fluoro-, chloro-, bromo-, iodo, e.g. 2-iodobutane.

2-iodobutane same as
•The chemical properties of alkyl halides take place at the halogen atom
so the functional group here is X atom.

•Alkyl halides are classified and named depending on

how many R groups are attached to the carbon that is directly attached to the

• A primary carbon (1o) has 1 R group, a secondary (2 o) has two R groups

and a tertiary carbon (3 o) has 3 R groups attached to it.

•If there are no R groups attached to the C connected to the halogen,

it’s a methyl halide (CH3X)..
 Alkyl halides:
The following illustrates the differences among methyl, primary,
secondary and tertiary alkyl halides
 Alcohols
•Alcohols have the general formula of R-OH in which R is an alkyl or aryl
(aromatic) i.e. hydrogen on a hydrocarbon is replaced by at least one OH
group.

•Alcohols are named by dropping the e of the parent hydrocarbon & adding ol.
The OH is assigned a position on the chain, by numbering from the OH that is
closest to the end.

•Thus, methane becomes 1-methanol or simply methanol and

ethane becomes 1-ethanol or just ethanol, 1-propanaol or simply propanol.
The last example is 2-propanol indicating that the OH is in position 2
from either side of the hydrocarbon chain.
 Alcohols
Number IUPAC Molecular Condensed Structural
of carbon name formula structural formula
atom(s) formula
1 Methanol CH3OH CH3OH

2 Ethanol C2H5OH CH3CH2OH

3 Propan-1- C3H7OH CH3CH2CH2OH

ol

4 Butan-1- C4H9OH CH3CH2CH2CH2OH

ol

New Way Chemistry for Hong Kong A-Level 3A

The first four members of straight-chain alcohols
18
 Alcohols
Just like alkyl halides, alcohols are classified and named depending on how
many R groups are attached to the carbon that is directly attached to the OH.
The number of carbon atoms directly attached to the carbon bonded to the
OH will dictate whether it will be methyl alcohol, primary, secondary
or tertiary, see illustration below.

methanol ethanol 2-propanol Tertbutyl alcohol or tert butanol

 Amines

•Amines are derivatives of ammonia (NH3) in which 1 or more H atoms are

replaced by organic groups (alkyl or aryl groups).

•Amines are also classified as primary, secondary or tertiary depending on

how many H atoms are replaced i.e. how many alkyl groups are attached to
the nitrogen. Note that, the designation of whether primary, secondary or
tertiary is different from alcohols.

For alcohols, the type of carbon atom (1o, 2o, 3o) bound to the -OH group
determines whether the alcohol was primary, secondary, or tertiary.

•For amines, it is the number of carbon groups that are bound to the
nitrogen.
 Amines
•The classification as 1o, 2o, and 3o classification is important and must be
distinguished from alcohol naming

• For tert-butyl alcohol is a tertiary alcohol because 3 carbon atoms are

attached to a carbon atom bonded directly to the OH group.

• But, tertbutyl amine is a primary amine because only 1 carbon atom is

directly bonded to the nitrogen atom.
 Aldehydes and Ketones
•In aldehydes and ketones, the C=O functional group is called
the “carbonyl group”.

In aldehydes, the carbonyl group is always joined to at least one hydrogen,

meaning it is always on the end.

To name aldehydes: identify longest chain containing the carbonyl group,

then the -e ending replaced by -al, such as methanal, ethanol, propanal etc.
 Aldehydes and Ketones
• In Ketones, the carbon of the carbonyl group is joined to two other
carbons meaning it is never at the end of the parent chain.

To name ketones: identify longest chain containing the carbonyl group,

then the -e ending replaced by the new ending of the lowest hydrocarbon
chain is –one and the position of the carbonyl is given the lowest count number

For example, 2-butanone, 3-pentanone, 2-pentanone.

 Carboxylic Acids
•Carboxylic acids also have a carbonyl group (C=O), but is also attached to
a hydroxyl group (-OH) = “carboxyl” group.
•The general formula is R-COOH.
These are named by identifying the longest continuous carbon chain
(i.e. the alkane) that contains the carboxyl group
and then dropping the –e and replacing with -oic acid.

•Examples are methanoic acid, ethanoic acid and propanoic acid,

and 2-methylpropanoic acid.
Self-assessment Activities
1. What is the functional group in alkyl halides, alcohols, amines & carboxylic acids?

2. What are alkyl halides and on what basis are they classified methyl, primary,
secondary or tertiary? Use the compounds below to explain your answer.

Also provide names for the above compounds.

3. What is the basis of classifying amines as primary, secondary or tertiary using

the following compounds to illustrate your answer?
CH3 CH3
:

N H2 N -H CH2 -N-CH3
:

:
4.Explain(a how the
Aniline
1° aromatic classification
amine ) (a 2° aromaticof alcohols
N-Me th ylaniline
amine ) (adiffers
3° aliphatic from
amin e) amines as primary, secondary
B e nzyldimet hylamin e

or tertiary.
5.With a reason identify the functional group present in the following molecules?
Name this compound as well.
 C. Elemental Analysis of Organic Compounds.
Carbon, Hydrogen, Nitrogen. Sulfur, Oxygen (CHNSO) Analysis

Basic Principles
Elemental analysis is the qualitative detection and quantitative determination
of chemical elements (atoms, ions) in a sample.

The aim of elemental organic analysis in general is the determination of

the elemental composition of organic compounds. Major constituents of
organic substances are C, H, N, S and O besides halogens, P and metals.

CHNSO elemental analysers provide a means for the rapid determination of

carbon, hydrogen, nitrogen and sulphur in organic compounds.

The analysis can be done on a variety of sample types such as solids,

liquids, volatile and viscous samples in various industries.
The sample should be as pure as possible and completely dry.
 Elemental Analysis of Organic Compounds.
Carbon, Hydrogen, Nitrogen. Sulfur, Oxygen (CHNSO) Analysis
•In a typical CHNSO analyzer,:
carbon is converted to CO2; hydrogen to H2O; nitrogen to N2 gas
and oxides of nitrogen and sulphur to SO2, in a furnace at 1000o.
•The combustion products are swept out of the combustion chamber by helium
and passed over heated high purity copper at 600o C.
The copper removes any oxygen not consumed in the initial combustion
and converts any oxides of nitrogen to nitrogen gas.
•The gases are then passed through traps in order to leave only
carbon dioxide, water, nitrogen and sulphur dioxide.

Detection and Quantification of CO2

,H2O, N2, and SO2 is done by gas
chromatography (GC) s
Using high purity standard compounds
and a suitable detector.
 Qualitative and Quantitative Analysis of Organic Compounds.
Example 1
In chemistry, the chemical analysis designed to identify the components of a substance or
mixture is called qualitative analysis of that substance. On the other hand, quantitative
analysis is the determination of the amount expressed as a concentration or percentage of
the various components in a sample. Qualitative Analysis tells 'what' is in a sample, while
Quantitative analysis is used to tell 'how much' is in a sample.

In the CHNSO analysis, the output (report) shows the elements present in a sample
(qualitative) and the percentage amount of each element (quantitative). From the detected
gases nitrogen (N2, molar mass is 28), carbon dioxide (CO2, molar mass is 44), water vapor
(H2O, molar mass is 18) and sulfur dioxide (SO2, molar mass is 64), the percent amount for
the individual elements CHNSO and then be calculated as follows:

If the sample does not contain any other

elements, the percent for oxygen, % O,
can be found by adding up all the other
percent compositions (%C, %H, %N, %S)
and subtracting from 100 %.
Qualitative and Quantitative Analysis of Organic Compounds.
Empirical and Molecular Formula Determination.
Empirical and Molecular Formula Determination.
Empirical and Molecular Formula Determination.
Empirical and Molecular Formula Determination.
Empirical and Molecular Formula Determination.
Empirical and Molecular Formula Determination.