CH 110-Topic 8 Notes – ORGANIC CHEMISTRY

Contents
6.1. REFERENCES FOR ORGANIC CHEMISTRY..................................................................................... 1
6.2. INTRODUCTION TO ORGANIC CHEMISTRY ................................................................................. 1
6.3. ALKANES – SATURATED HYDROCARBONS .................................................................................. 1
6.3.1. ISOMERISM IN ALKANES ............................................................................................................ 2

6.3.2. NOMENCLATURE OR NAMING OF ALKANES ................................................................................... 3

6.3.2.1 Rules for Naming Alkanes ................................................................................................... 3

6.3.3. REACTIONS OF ALKANES ............................................................................................................ 5

6.3.4. CYCLIC ALKANES ....................................................................................................................... 6

6.3.4.1 Nomenclature of Cycloalkanes ........................................................................................... 6

6.4. ALKENES AND ALKYNES– UNSATURATED HYDROCARBONS ....................................................... 6
6.4.1. ALKENES ................................................................................................................................. 7

6.4.1.1 Nomenclature of Alkenes ................................................................................................... 7

6.4.1.2 Cis – Trans Isomerism ......................................................................................................... 7
6.4.2. ALKYNES ................................................................................................................................. 7

6.4.2.1 Nomenclature of Alkynes.................................................................................................... 7

6.4.3. REACTIONS OF ALKENES AND ALKYNES ......................................................................................... 8

6.5. AROMATIC HYDROCARBONS ...................................................................................................... 9

6.5.1. REACTIONS OF AROMATIC HYDROCARBONS ................................................................................ 10

6.5.2. NOMENCLATURE OF AROMATIC HYDROCARBONS ......................................................................... 10

6.6. HYDROCARBON DERIVATIVES ................................................................................................... 11

6.6.1. ALCOHOLS ............................................................................................................................ 12

6.6.1.1 Rules for Naming and Classifying Alcohols ....................................................................... 12

6.6.1.2 Boiling Points of Alcohols .................................................................................................. 13
6.6.1.3 Methanol and Ethanol ...................................................................................................... 13
6.6.1.4 Other Types of Alcohols .................................................................................................... 13
6.6.1.5 Reactions of Alcohols ........................................................................................................ 13
6.6.2. ETHERS ................................................................................................................................ 14

6.6.3. ALDEHYDES AND KETONES ....................................................................................................... 14

6.6.2.1 Nomenclature of Ketones and Aldehydes ....................................................................... 14

6.6.2.2 Some Common Ketones and Aldehydes ........................................................................... 14
6.6.2.3 Uses and Properties of Ketones and Aldehydes ............................................................... 15
6.6.4. CARBOXYLIC ACIDS AND ESTERS ................................................................................................ 16

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 CH 110-Topic 8 Notes – ORGANIC CHEMISTRY

6.6.4.1 Nomenclature of Carboxylic Acids .................................................................................... 16

6.6.4.2 Production of Carboxylic Acids ..................................................................................... 16
6.6.4.3 Reactions of Carboxylic Acids........................................................................................ 16
6.6.5. AMINES ................................................................................................................................ 17

6.6.5.1 Nomenclature of Amines .................................................................................................. 17

6.6.5.2 Properties of Amines..................................................................................................... 17

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 CH 110-Topic 8 Notes – ORGANIC CHEMISTRY

8.1 REFERENCES FOR ORGANIC CHEMISTRY

Steven S Zumdahl and Susan A Zumdahl, (2010), Chemistry, 8th Edition, Brooks/Cole Centage
Learning, Belmont, CA, USA, pp 1005-1064.
Steven S Zumdahl and Susan A Zumdahl, (2013), Chemistry, 9th Edition, Brooks/Cole Centage
Learning, Belmont, CA, USA, pp 1023-1085.
Darrell D Ebbing and Steven D Gammon, (2009), General Chemistry, 9th Edition, Brooks/Cole
Centage Learning, Belment, CA, USA, pp 968-1003
Raymond Chang, (2010), Chemistry, 10thEdition, McGraw Hill Higher Education, New York,
USA, pp 1024-1056

8.2 INTRODUCTION TO ORGANIC CHEMISTRY

Group 4A or (IVA) elements carbon and silicon form most of the natural substances.

• Silicon forms chains and rings containing Si-O-Si bridges that produce silica and
silicates forming geological materials like rocks, sands and soils. This is the study of
Geology in the field of Mineral Sciences and Soil Sciencein the field of Agricultural or
Natural Resources Sciences.
• Carbon forms strong bonds to itself to form long chains and rings of carbon atoms. It
also bonds to other non-metals such as H, N, O, and halogens. The study of carbon-
containing compounds and their properties is called Organic Chemistry.

8.3. ALKANES – SATURATED HYDROCARBONS

The simplest class of organic compounds are hydrocarbons. In an introductory organic
chemistry course like this one, other organic compounds studied in it are considered as
derivatives of hydrocarbons.

Hydrocarbonsare compounds composed of carbon and hydrogen.Figure 6.1 shows that the
two classes of hydrocarbons are saturated and unsaturated hydrocarbons.

Figure 8.1: Classification of Hydrocarbons

Hydrocarbons

Aromatic
Aliphatic
(Unsaturated cmpds)

Alkanes Cycloalkanes Alkenes Alkynes

(saturated cmpds) (saturated compds) (Unsaturated cmpds) (Unsaturated cmpds)

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 CH 110-Topic 8 Notes – ORGANIC CHEMISTRY

On the basis of structure, hydrocarbons can be divided into two main classes – aliphatic and
aromatic. Aliphatic hydrocarbonsdo not contain the benzene group,or the benzene ring
whereas aromatic hydrocarbonscontain one or more benzene rings.

Those compounds whose carbon-carbon bonds are all single bonds are said to be saturated
since each carbon is bound to four atoms, the maximum number required by the octet rule
for a 2nd period element, that carbon is.

Hydrocarbons containing carbon-carbon multiple bonds are described as unsaturated since

the carbon atoms involved in a multiple bond can react with additional atoms, as shown by
the addition of hydrogen to ethylene.

CH 2 = CH 2 + H 2 ⎯⎯→
Ni
CH 3 − CH 3 Equation 1

H|  H|  H|
 
All alkanes can be represented by the general formula H − C| −  C|  − C| − H or
H  H  n H
CH 3 − (CH 2 ) n − CH 3 or C n H 2n +2 where n is an integer.

In saturated hydrocarbons since each carbon atom is bonded to four other atoms, the
carbon atom is described as sp3 hybridised.

Methane (CH4) is the simplest alkane and the table below (Table 22.1 of Zumdahl and
Zumdahl 8th Edition on page 1008) shows the first 10 alkanes.

Table 8.1: Selected Properties of the First Ten Normal Alkenes

No. of Structural
Name Formula Molar Mass Melting Point (oC) Boiling Point (oC)
Isomers
Methane CH4 16 -183 -162 1
Ethane C2H6 30 -172 -89 1
Propane C3H8 44 -187 -42 1
Butane C4H10 58 -138 0 2
Pentane C5H12 72 -130 36 3
Hexane C6H14 86 -95 68 5
Heptane C7H16 100 -91 98 9
Octane C8H18 114 -57 126 18
Nonane C9H20 128 -54 151 35
Decane C10H22 142 -30 174 75
8.3.1 ISOMERISM IN ALKANES
Alkanes in which the carbon atoms form long “strings” or chains are called normal or
straight-chain or unbranched hydrocarbons. Butane and succeeding alkanes show
structural isomerism. Structural isomerism occurs when molecules have the same atoms but
different bonds. Butane can exist as a straight chain molecule (normal butane, or n-butane)
or as a branched-chain structure (isobutane).

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 CH 110-Topic 8 Notes – ORGANIC CHEMISTRY

H|
CH 3 − CH 2 − CH 2 − CH 3
CH 3 − C| − CH 3
or
CH 3
n − butane, bp = −0.5 o C
isobutane, bp = −12 o C

Because of their different structures, these molecules show different properties.

8.3.2 NOMENCLATURE OR NAMING OF ALKANES

There are lots of organic compounds. There are 20 million synthetic and natural organic
compounds compared to 100,000 inorganic compounds. This necessitates systematic
method of naming them since common names can’t all be memorised. The systematic
method of naming compound uses the International Union of Pure and Applied Chemistry
(IUPAC) system.
8.3.2.1 Rules for Naming Alkanes
1. Names of the alkanes beyond butane are obtained by adding the suffix –ane to the
Greek root of the number of carbon atoms (pent- for five, hex- for six, etc). For branched
hydrocarbons, the longest continuous chain of carbon atom gives the root name for the
hydrocarbon. For example, in the alkane
CH 3
|
C H2
| six carbons
C H2
|
CH 3 − CH 2 − C H − CH 2 − CH 3

The largest chain contains six carbon atoms and this compound is named a hexane.
2. When alkane groups appear as substituents, they are named by dropping the –ane and
adding –yl. –CH3 is obtained by removing a hydrogen atom from methane and is called
methyl, –C2H5 is called ethyl, –C3H7 is called propyl, etc as shown in the table below.
Table 8.2: The Most Common Alkyl Substituents and Their Names (Table 22.2 of
Zumdahl&Zumdahl 8th Edition, pp 1009)
Structure Name
− CH3 Methyl
− CH 2CH 3 Ethyl
− CH 2CH 2CH3 Propyl
|
CH 3 C HCH 3 Isopropyl
− CH2CH2CH2CH3 Butyl
|
CH 3 C HCH 2CH 3 Sec-butyl
H
|
− CH 2 − C − CH 3 Isobutyl
|
CH 3
CH 3
|
− C − CH 3 Tert-butyl
|
CH 3

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 CH 110-Topic 8 Notes – ORGANIC CHEMISTRY

3. The positions of substituent group are specified by numbering the longest chain of
carbon atoms sequentially, starting at the closest end to the branching. For example, the
compound below is called 3-methylhexane NOT 4-methylhexane.

CH 3
|
C H3 − C H 2 − C H − C H 2 − C H 2 − C H3 Correct Numbering
1 2 3 4 5 6

CH 3
|
C H3 − C H 2 − C H − C H 2 − C H 2 − C H3 Incorrect Numbering
6 5 4 3 2 1

NB: Note the hyphen placed between number and substituent name.

4. The location and name of each substituent are followed by the root alkane name. The
substituents are listed in alphabetical order (irrespective of any prefix) and the prefixes
di, tri, etc are used to indicate multiple, identical substituents.

Sample Exercise 22.2 of Zumdahl and Zumdahl, 8th Edition, pp 1010 on ISOMERISM AND
NOMENCLATURE: Draw the structural isomers for the alkane C6H14, and give the
systematic name for each one.

Solution:

Proceeding systematically by starting with the longest chain and rearranging the carbon
atoms to form shorter branched chains we have the following answers

1. C H3 C H 2 C H 2 C H 2 C H 2 C H3 Hexane
1 2 3 4 5 6

2. By taking out one carbon atom & making it a methyl substituent at 2nd C atom, we have
CH 3
|
C H3 C H C H 2 C H 2 C H3 2 - Methylpentane
1 2 3 4 5

3. By putting methyl substituent at 3rd carbon atom, we have

CH 3
|
C H3 C H 2 C H C H 2 C H3 3 - Methylpentane
1 2 3 4 5

4. By taking out two carbon atoms out of the original six-member chain and making two
methyl substituents at 2nd and 3rd carbon atoms, we have
CH 3 CH 3
| |
C H3 − C H − C H − C H3 2,3 - Dimethylbutane
1 2 3 4

5. By putting two methyl groups on the same carbon in the above structure, we have
CH 3
|
C H 3 − C− C H 2 − C H 3 2,2 - Dimethylbutane
1 | 3 4
CH 3

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 CH 110-Topic 8 Notes – ORGANIC CHEMISTRY

Sample Exercise 22.3 of Zumdahl and Zumdahl, 8th Edition, pp 1011 on STRUCTURES FROM
NAMES: Write the structure for each of the following compounds.
(a) 4-ethyl-3,5-dimethylnonane
(b) 4-tert-butylheptane

Solution:
(a) The root name is nonane. This signifies a nine-carbon chain. Thus we have
C H3
|

C H3 C H C H3
| | |

C H3 C H2 C H C H C H C H2 C H2 C H2 C H3
1 2 3 4 5 6 7 8 9
|

(b) Heptane signifies a seven-carbon chain, and tert-butyl group is CH 3 − C| − CH 3 . Thus we

CH 3
C H3
|

have CH 3 − C− CH 3
|

C H3 C H 2 C H2 C H C H 2 C H2 C H3
1 2 3 4 5 6 7

8.3.3 REACTIONS OF ALKANES

Alkanes are fairly unreactive because (i) they are saturated compounds and (ii) the C-C and
C-H bonds are relatively strong.

1. At high temperatures alkanes vigorously react exothermically with oxygen in

combustion reactionsthat are a basis for their widespread use as fuels.

For example, the reaction of butane (that is, cigarette lighter fuel) with oxygen gives
2C4H10 (g) +13O2 (g)→8CO2 (g) +10H2O(g)
2. Alkanes can also undergo substitution reactions primarily where halogen atoms replace
hydrogen atoms

For example successive chlorination of methane

CH 4 + Cl 2 ⎯
⎯→
hν
CH 3Cl + HCl ; CH 3Cl + Cl 2 ⎯
⎯→
hν
CH 2Cl 2 + HCl ;
Chloromethane Dichloromethane

CH 2Cl 2 + Cl 2 ⎯
⎯→ CHCl 3 + HCl ;
hν
CHCl 3 + Cl 2 ⎯
⎯→
hν
CCl 4 + HCl
T richloromethane T etrachloromethane
or (Chlorofor m) or (Carbon tetracloride)

hν is ultraviolet light used to break Cl − Cl bond to produce chlorine atoms

Cl 2 →Cl. + Cl. which are very reactive and able to attack C− H bonds.
3. Alkanes also can undergo dehydrogenation reactions in which hydrogen atoms are
removed and the product is an unsaturated hydrocarbon.

For example: CH 3CH 3 ⎯Cr⎯

⎯
2O3
o
→ CH 2 = CH 2 + H 2
500 C Ethylene

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8.3.4 CYCLIC ALKANES OR CYCLOALKANES

Besides forming chains, carbon atom also form rings. The cyclic alkanes are of the general
formula C n H 2n and the first are shown in Table 6.3 below.

Table 8.3: First Five Cycloalkanes

Formula Name Structure Comment
Quite reactive
C3H6 Cyclopropane because of strained
or C-C bond
C4H8 Cyclobutane
or

C5H10 Cyclopentane
or
C6H12 Cyclohexane
or

C4H8 Methylcyclopropane
or

8.3.4.1 Nomenclature of Cycloalkanes

Nomenclature of cycloalkanes follows the same rules as for the other alkanes except that
the root name is preceded by the prefix cyclo-. The ring is numbered so as to give the
smallest substituent numbers.
Sample Exercise 22.4 of Zumdahl and Zumdahl, 8th Edition, pp 1014 on NAMING CYCLIC
ALKANES: Name each of the following cyclic alkanes.
(a) CH 3 − C H − CH 3
|

CH 3

(b) CH 2CH 3

CH 2CH 2CH 3
Solution:
(a) The six-carbon cyclohexane ring is numbered as follows: There is an isopropyl group at
carbon 1 and a methyl group at carbon 3. The name is 1-isopropyl-3-methylcyclohexane
since the alkyl groups are named in alphabetical order.
(b) This is a cyclobutane ring which is numbered as follows: There is an ethyl group at
carbon 1 and a propyl group at carbon 2 since numbering is in alphabetical order. The
name is 1-ethyl-2-propylcyclobutane.

8.4. ALKENES AND ALKYNES– UNSATURATED HYDROCARBONS

Multiple carbon-carbon bonds result when hydrogen atoms are removed from alkanes.
Aliphatic hydrocarbons that have multiple bonds are termed unsaturated hydrocarbons.

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8.4.1 ALKENES
Aliphatic hydrocarbons with carbon-carbon double bonds are called alkenes. Those with a
single double bond have a general formula Cn H 2n . The simplest alkene, C2H4, has a simple
name of ethylene. Its Lewis structure is shown below and carbon atoms are sp2 hybridised.

The C-C σ bond formed by sharing electron pair between sp2orbtials and the π bond is
formed by sharing a pair of electrons between p orbitals.

8.4.1.1 Nomenclature of Alkenes

Nomenclature of alkenes is similar to that of alkanes
1. The root hydrocarbon name ends in –ene rather than –ane. Thus the systematic name
for C2 H 4 or CH 2 = CH 2 is ethene and C3H6 or CH 2 = CHCH 3 is propene.
2. In alkenes with more than three carbon atoms, the location of the double bond is
indicated by the lowest numbered carbon atom involved in the bond. Thus
CH2=CHCH2CH3 is 1-butene and CH3CH=CHCH3 is 2-butene.

8.4.1.2 Cis – Trans Isomerism

The p orbitals on the double bonded carbon atoms like ethylene must be lined up (parallel)
to allow formation of the π bond. This prevents rotation of two CH2 groups relative to each
other at ordinary temperatures when compared to alkanes where rotation is possible. The
restricted rotation about doubly bonded carbon atoms means that alkenes exhibit cis-trans
isomerism.

(a) Cis-2-butene (b) trans-2-butene

In the cis isomer, substituents are on the same side of the double bond while in the trans
isomer, substituents are on opposite sides of the double bond.

8.4.2 ALKYNES
Alkynes are unsaturated hydrocarbons with a triple bond. The simplest alkyne C2H2or
H − C  C − H that is commonly called acetylene has a systematic name of ethyne. A triple
bond consists of aσ bond between sp hybrid orbitals on two carbon atoms and two π bonds
involving two 2p orbitals on each carbon atom.

8.4.2.1 Nomenclature of Alkynes

Nomenclature of alkynes involves use of –yne as suffix to replace the –ane of the parent
alkane. Thus CH 3 − CH 2 − C  C − CH 3 or CH 3CH 2C  CCH 3 has the name 2-pentyne.

Like alkanes, unsaturated hydrocarbons can exist as ringed structures for example two
examples below.

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 CH 110-Topic 8 Notes – ORGANIC CHEMISTRY

4-Methylcylopentene
We are to note that for cycloalkenes, numbering of the carbon atoms of the ring is through
the double bond toward the substituent.

Sample Exercise 22.5 of Zumdahl and Zumdahl, 8th Edition, pp 1014 on NAMING ALKENES
AND ALKYNES: Name each of the following molecules.
(a) H CH 3 (b) CH 3CH 2C  CCHCH 2CH 3
C=C CH 2
CH 3CH 2CH H CH 3
CH 3
Solution:
(a) The longest chain contains 6 carbon atoms and the chain is numbered as follows:
1
H C H3
3 2
C=C
6 5 4
C H3 C H 2 C H H

CH 3
Thus the hydrocarbon has a root name of 2-hexene. The hydrogen atoms are on
opposite sides of the double bond which means the molecule is a trans isomer with a
methyl substituent. The molecule is 4-methyl-trans-2-hexene.
(b) The longest chain consisting of seven carbon atoms is numbered as shown giving the
triple bond the lowest possible number
1 2 3 4 5 6 7
C H3 C H 2 C  C C H C H 2 C H3
CH 2
CH 3
The hydrocarbon is a 3-heptyne. Full name is 5-ethyl-3-heptyne, where the position of
the triple bond is indicated by the lowest-numbered carbon atom involved in this bond.

8.4.3 REACTIONS OF ALKENES AND ALKYNES

The most important reactions of these unsaturated aliphatic hydrocarbons are addition
reactions in which C-C π bonds, which are weaker than C-C σ bonds are broken and new σ
bonds are formed to the atoms being bond.

For example, hydrogenation reactions involve the addition of hydrogen atoms.

CH 2 = CHCH 3 + H 2 ⎯⎯→
Pt
CH 3CH 2CH 3 or
Propene Propane

The catalyst serves to help break the relatively strong H-H bond.

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Halogenation reaction of unsaturated hydrocarbons involves addition of halogen atoms. For

example,
CH 2 = CHCH 2CH 2CH 3 + Br2 ⎯
⎯→ CH 2 BrCHBrCH 2CH 2CH 3
Pentene 1,2- Dibromopentane

Hydrohalogenation reaction is the (electrophilic) addition of hydrohalic acids like hydrogen

chloride or hydrogen bromide to alkenes to yield the corresponding haloalkanes. For
example
CH 2 = CHCH 2CH 2CH 3 + HBr ⎯
⎯→ CH 3CHBrCH 2CH 2CH 3
Pentene 2 - Bromopentane

If the two carbon atoms at the double bond are linked to a different number of hydrogen
atoms, the halogen is found preferentially at the carbon with fewer hydrogen substituents,
an observation known as Markovnikov’s rule.

Another important reaction of unsaturated hydrocarbons, is polymerisation, a process in

which many small molecules are joined together to form a large molecule

8.5 AROMATIC HYDROCARBONS

This is a special class of unsaturated hydrocarbons. The simplest is benzene with a planar
ring structure whose main characteristics are shown in Figure 6.2 below.

Figure 8.2: Representations of Benzene

http://en.m.wikipedia.org/wiki/File:Benzene_Representations.svg
In the localised electron model of the bonding in benzene, its resonance structures (also
known as Kekule structures) are used to account for the known equivalence of all the
carbon-carbon bonds.

The best description of the benzene molecule assumes sp2 hybrid orbitals on each carbon
atom that is used to form two C-C σ bonds and one C-H σ bond with the remaining 2p orbital
on each carbon used to form π molecular orbitals. Delocalisation of these π electrons is
usually shown by a circle inside the ring.

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 CH 110-Topic 8 Notes – ORGANIC CHEMISTRY

8.5.1 REACTIONS OF AROMATIC HYDROCARBONS

Delocalisationof the π electrons makes benzene behave differently from a typical
unsaturated hydrocarbon. Benzene, unlike other unsaturated hydrocarbons DOES NOT
UNDERGO RAPID ADDITION REACTIONS. Rather, it undergoes substitution reactions where
hydrogen atoms are replaced by other atoms.

FeCl3 or AlCl3

Chlorobenzene

AlCl3

Toluene
The first reaction is catalysed by FeCl3 or AlCl3. The second reaction is catalysed by H2SO4
while the third reaction is catalysed by AlCl3.

In summary:
• Substitution reactions are characteristic of saturated hydrocarbons
• Addition reactions are characteristic of unsaturated hydrocarbons
• Benzene’s substitution reactions show stability due to electron delocalisation.

8.5.2 NOMENCLATURE OF AROMATIC HYDROCARBONS

This is similar to nomenclature for saturated ring systems. Numbers are used if more than
one substituent to indicate positions occupied on the ring. For example,

1,2-dichlorobenzene 1,3-Dichlorobenzene 1,4-Dichlorobenzene

(ortho-dichlorobenzene or (meta-dichlorobenzene or (para-dichlorobenzene or
o-dichlorobenzene) m-dichlorobenzene) p-dichlorobenzene)

The names in brackets for an alternative nomenclature. Other examples are

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 CH 110-Topic 8 Notes – ORGANIC CHEMISTRY

Methylbenzene 3-Bromonitrobenzene 3-Chlorotoluene

(Toluene) (m-Bromonitrobenze) (m-chlorotoluene)

When benzene is used as a substituent, it is called the phenyl group.

CH 3 − CH − CH 2CHCH 2CH 3
Cl

Phenyl group 4-Chloro-3-phenylhexane

8.6 HYDROCARBON DERIVATIVES

A lot of organic molecules contain other elements in addition to carbon and hydrogen. But
they can be viewed as hydrocarbon derivatives, molecules that are fundamentally
hydrocarbons but have additional atoms or groups of atoms called functional groups.
Common functional groups are shown in the table below.

Table 8.4: Common Functional Groups

Class Functional Group General Formula* Example
Iodomethane
Halohydrocarbons − X(F, Cl, Br, I) R −X (methyl iodide)
CH3OH
Alcohols − OH R − OH Methanol
(Methyl alcohol)
CH3 − O − CH3
Ethers −O− R − O − R'
Dimethyl ether
CH 2 O
O|| O||
Aldehydes Methanal
− C− H R − C− H
(Formaldehyde)
O||
O|| O|| CH 3 − C − CH 3
Ketones Propanone
− C− R − C − R'
(Dimethyl ketone or
acetone)
CH 3COOH
O O||
Carboxylic Acids ||
Ethanoicacid
− C − OH R − C − OH
(Acetic Acid)
CH3COOCH 2CH3
O|| O||
Esters Ethylethanoate
− C− O − R − C − O − R'
(Ethyl acetate)
CH3 NH 2
Amines − NH 2 R − NH 2 Aminomethane
(Methyl amine)
*R and R’ represent hydrocarbon fragments
Each functional group exhibits characteristic chemistry and are considered separately below.

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8.6.1 ALCOHOLS
Alcohols are characterised by presence of –OH group. Table 6.5 below gives common
alcohols.

Table 8.5: Common Alcohols

Formula Systematic Name Common Name
CH3OH Methanol Methyl alcohol
CH3CH 2OH Ethanol Ethyl alcohol
CH3CH 2CH 2OH 1-propanol n-propyl alcohol
CH 3 C HCH 3
| 2-propanol Isopropyl alcohol
OH
8.6.1.1 Rules for Naming and Classifying Alcohols
The systematic name for an alcohol is obtained by replacing the –e of the parent
hydrocarbon by –ol. The position of the –OH group is specified by a number (where
necessary) chosen so that it is the smallest of the substituent numbers.

Alcohols are classified according to the number of hydrocarbon fragments bonded to the
carbon where the –OH group is attached as shown below where R, R’ and R” (which may be
the same or different) represent hydrocarbon fragments.

R|
R|
R − CH 2OH R − C − OH
'

R − C − OH
'
|
Primary Alcohol R"
Secondary alcohol
(one R group) Tertiary alcohol
(two R groups
(three R groups)

Sample Exercise 22.6 of Zumdahl and Zumdahl, 8th Edition, pp1022 on NAMING AND
CLASSIFYING ALCOHOLS: For each of the following alcohols, give the systematic name and
specify whether the alcohol is primary, secondary or tertiary.
CH 3
|
CH 3 C HCH 2CH 3
(a) | (b) ClCH 2CH 2CH 2OH (c) CH 3 C CH 2CH 2CH 2CH 2 Br
OH |
OH
Solution:
1 2 3 4

(a) The chain is numbered as follows C H 3 C| H C H 2 C H 3 .

OH
The compound is called 2-butanol since the –OH group is located at the number 2
position of the four carbon chain. Note that the carbon to which the –OH group is
attached has also two R groups, namely − CH3 and − CH 2CH 3 attached to it. Thus this
is a secondary alcohol.
3 2 1
(b) The chain is numbered as follows Cl C H 2 C H 2 C H 2OH .
The name is 3-chloro-1-propanol. This is a primary alcohol.

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CH 3
1 | 3 4 5 6
(c) The chain is numbered as follows C H 3 C C H 2 C H 2 C H 2 C H 2 Br .
|
OH
The name is 6-bromo-2-methyl-2-hexanol. This is a tertiary alcohol because the carbon
where the –OH group is attached also has three other R groups attached to it.

8.6.1.2 Boiling Points of Alcohols

Alcohols usually have much higher boiling points than might be expected from their molar
masses because of their polar –OH groups that produces extensive hydrogen bonding similar
to that found in water.

For example methanol with a molar mass of 30 g/mol has a boiling point of 65oC while
ethane with a molar mass of 30 g/mol has a boiling point of -89oC.

8.6.1.3 Methanol and Ethanol

These are alcohols of greatest commercial value whose industrial preparation is as follows:

1. Methanol (or wood alcohol) is prepared by hydrogenation of carbon monoxide

400 o C, ZnO/Cr O
according to the reaction equation CO + 2H2 ⎯⎯ ⎯ ⎯ ⎯ ⎯→ CH 3OH .
2 3

2. Ethanol in
(a) beverages is prepared by fermentation of glucose in corn, barley, grapes, etc
according to the reaction equation C6 H12O6 ⎯Yeast, enzymes
⎯⎯⎯⎯⎯→ 2 CH 3CH 2 OH + 2CO 2
Glucose Ethanol
(b) commercial applications such as a solvent for organic chemicals or as a starting
compound for the manufacture of dyes, synthetic drugs, cosmetics, etc is produced
by the reaction of water with ethylene according to the reaction equation
H SO
CH 2 = CH 2 + H 2 O ⎯⎯2 ⎯
⎯4
→ CH 3CH 2 OH

8.6.1.4 Other Types of Alcohols

1. Polyhydroxyl alcohols (that is, alcohols with more than one –OH group. For example

C H 2 − OH C H 2 − OH
(i) | and |
CH 2 − OH (ii) C H 2 − OH
1,2 − Ethanediol(or EthyleneGlycol) |
CH 2 − OH
1,2,3 − Propanetriol (or Glycerol or Glycerin)
2. Aromatic alcohols (that is, alcohols with a benzene ring).For example

− OH

Phenol
8.6.1.5 Reactions of Alcohols
Ethanol is the only nontoxic (more properly, the least toxic) of the straight-chain alcohols.
The enzyme alcohol dehydrogenase produced by the human body, helps to metabolize
ethanol by oxidising to acetaldehyde:
alcoholde hydrogenase
CH 3CH 2 OH ⎯⎯ ⎯⎯ ⎯ ⎯ ⎯⎯→ CH 3CHO + H 2 .
acetaldehyde

Ethanol can also be oxidised by inorganic agents, such as acidified dichromate, to

acetaldehyde and acetic acid:

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2− +
7 , H+
CH 3CH 2 OH ⎯Cr
⎯2O⎯ ⎯→ CH 3CHO ⎯Cr
⎯2O⎯ ⎯→ CH 3COOH .
2-
7 ,H

acetaldehy de

The alcohols are very weakly acidic: they do not react with strong bases, such NaOH. The
Alkali metals react with alcohols to produce hydrogen:

2CH 3OH + 2Na ⎯

⎯→ 2CH 3ONa + H 2
sodium methoxide

However this reaction is less violent than that of Na and water.

8.6.2 ETHERS
Ethers contain the R-O-R’ linkage, where R and R’ are a hydrocarbon (aliphatic or aromatic)
group. They are formed by the reaction between an alkoxide (containing RO − ion) and an
alkyl halide:

NaOCH 3 + CH 3 Br ⎯ ⎯→ CH 3OCH 3 + NaBr

sodium methoxide methyl bromide dimethyl ether

Diethyl ether is prepared on an industrial scale by heating ethanol with sulphuric acid at
140oC.

C 2 H 5OH + C 2 H 5OH ⎯
⎯→ C 2 H 5OC 2 H 5 + H 2 O

This is an example of a condensation reaction, which is characterised by the joining of two

molecules and the elimination of small molecule, usually water.

Like alcohols, ethers are extremely flammable. When left standing in air, they slowly tend to
form explosive peroxides

8.6.3 ALDEHYDES AND KETONES

O||
These contain the carbonyl group − C − . In aldehydes the carbonyl group is bonded to at
O||
least one hydrogen atom, as in methanal (formaldehyde), H − C − H or ethanal
O||
(acetaldehyde), CH 3 − C − H while in ketones, the carbonyl group is bonded to two carbon
O||
atoms as in propanone (acetone), CH 3 − C − CH 3 .

8.6.2.1 Nomenclature of Ketones and Aldehydes

Systematic name for an aldehyde is obtained from parent alkane by removing final –e and
adding –al. For ketones, the final –e is replaced by –one and the number indicates the
position of the carbonyl group where necessary. It should be noted that the aldehyde group
always occurs at the end of the carbon chain and the aldehyde carbon is always assigned as
number one for referencing substituent positions in the name.

8.6.2.2 Some Common Ketones and Aldehydes

1. Common Aldehydes

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 CH 110-Topic 8 Notes – ORGANIC CHEMISTRY

O|| O|| Cl
|
O||
(i) H − C− H (ii) CH 3 − C − H (iii) CH 3 C HCH 2 − C − H
Methanal Ethanal 3 − Chlorobutanal
(Formaldehyde) (Acetaldehyde)

(iv)
|
H−C=O
Benzaldehy de

2. Common Ketones

O|| O|| O||

(i) CH 3 − C − CH 3 (ii) CH 3 − C − CH 2CH 3 (iii) CH 3 − C − CH 2CH 2CH 3
2- Propanone 2 - Butanone 2- Pentanone
(Acetone) ( MethylEthylKetoneor MEK)

(iv)
|
O = C− CH 3
MethylPhenylKetone

8.6.2.3 Uses and Properties of Ketones and Aldehydes

1. Ketones have useful solvent properties used in industry. For example, acetone is as nail
polish remover in the cosmetics industry and a thinner for tippex used in offices

2. Aldehydes have odours. Pleasant odours have favourable use in the food industry. For
example,
(i) Vanillin gives pleasant odour of vanilla beans that used in the food industry.

H−C =O
|

− OCH 3
|
OH

(ii) Cinnamon aldehyde produces the characteristic odour of cinnamon

− CH = CH − C| = O
H
(iii) On the other hand, the unpleasant odour in rancid butter arises from the presence
of butanal (or butylaldehyde), CH 3CH 2CH 2 C| = O
H
3. Aldehydes and ketones are produced commercially by oxidation of alcohols. For
example,
(i) Mild oxidation of a primary alcohol gives a corresponding aldehyde
Mild oxidation
CH 3CH 2OH ⎯⎯ ⎯ ⎯ ⎯
⎯→ CH 3 C| = O
H
(ii) Oxidation of a secondary alcohol results in a ketone

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Oxidation
CH 3 C| H CH 3 ⎯⎯ ⎯⎯→ CH 3 − C|| − CH 3
OH O
8.6.4 CARBOXYLIC ACIDS AND ESTERS
Carboxylic acids are characterised by the presence of the carboxyl group − C|| − O − H and
O
have the general formula RCOOH . Typically, they are weak acids.

8.6.4.1 Nomenclature of Carboxylic Acids

Organic acids are named from the parent alkane by dropping final –e and adding –oic. Thus,
CH3COOH commonly called acetic acid has the systematic name of ethanoic acid. Other
examples below are

Cl − COOH
(i) CH 3CH 2CH 2COOH (ii) | (iii)
Butanoic acid CH 3 C HCH 2CH 2COOH
4 - Bromopentanoic acid
Benzoic acid

Cl
|
(iv) Cl − C COOH
|
Cl
Trichloroethanoicacid
(Trichloroacetic acid)

8.6.4.2 Production of Carboxylic Acids

Many carboxylic acids are synthesised by oxidising primary alcohols with a strong oxidising
agents. For example, ethanol can be oxidised to acetic acid using potassium permangate
KMnO (aq)
according to the reaction CH 3CH 2OH ⎯⎯ ⎯4⎯
⎯→ CH 3COOH

8.6.4.3 Reactions of Carboxylic Acids

A carboxylic acid reacts with an alcohol to form an ester and a water molecule. This is called
an esterification or a condensation reaction. For example, the reaction of ethanoic acid and
ethanol produces ethylethanoate according to the reaction equation

O|| O||
CH 3 C − OH + H − OCH 2CH 3 ⎯
⎯→ CH 3 C − OCH 2CH 3 + H 2O
Ethyl ethanoate
(Ethyl acetate)

Esters have sweet fruity odour that is in contrast to the often pungent odours of the parent
carboxylic acids. For example, the odour of bananas is from n-amyl acetate and that of
oranges is from n-octyl acetate.
O|| O||
CH 3 C − OCH 2CH 2CH 2CH 2CH 3 CH 3 C − OC8H17
n − Amyl acetate n − Octyl acetate
A very important ester can be formed from the reaction of salicylic acid and acetic acid as
shown below.

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 CH 110-Topic 8 Notes – ORGANIC CHEMISTRY

O|| O||
C − OH C − OH
⎯
⎯→
O − H + HO − C|| CH 3 O − C|| CH 3 + H 2O
O O
Acetylsalicylic acid (commonly known as aspirin) is
used as analgesic, that is, a pain killer.
8.6.5 AMINES
These compounds can be considered to be derivatives of ammonia in which one or more
N − H bonds are replaced by N − C bonds. Resulting amines are classified as primary if one
N-C bond is present, secondary if two N-C bonds are present and tertiary if all three N-H
bonds have been replaced by N-C bonds.

Formula Common Name Type Systematic Name

CH3NH2 Methyl amine Primary Aminomethane
CH3CH2NH2 Ethyl amine Primary Aminoethane
(CH3)2NH Dimethylamine Secondary
(CH3)3N Trimethylamine Tertiary
PhNH3 Analine Primary
PhNHPh Diphenylamine Secondary

8.6.5.1 Nomenclature of Amines

Common names used for simple amines, the systematic nomenclature for complex
molecules uses the name amino- for the -NH2 functional group. For example,
CH 3 − C HCH 2CH 3
| is named 2-aminobutane.
NH 2

8.6.5.2 Properties of Amines

Many amines are weak bases that have unpleasant “fish like” odours. For example, odours
associated with decaying animal/human tissue are due to amines such as putrescine and
cadaverine while the odour of human faeces is due to the amine called skatole.

H 2 NCH 2CH 2CH 2CH 2 NH 2 H 2 NCH 2CH 2CH 2CH 2CH 2 NH 2

Putrescine Cadaverine

CH 2CH 2 − NH 2
Skatole

N|
H

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