UNIVERSITY OF BURAO

FACULTY OF MEDICINE AND

HEALTH SCIENCE
1M1
ORGANIC CHEMISTRY COURSE
Chapter 3:
Alkanes and other functional groups

12/13/2018 Lecturer: Mohamed Mohamoud

Mohamoud Ibrahim
Organic Chemistry by: Mohamed
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 Functional Groups

• Hydrocarbons
• Alcohols
• Aldehydes & Ketones
• Carboxylic Acids
• Esters
• Amines

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 Functional Groups
Alcohol
 The functional group for alcohol is an hydroxyl group (-
OH)
 Alcohols are classified as primary (1°) , secondary (2°)
or tertiary (3°).

Aldehydes and Ketones

 The functional group of both aldehydes and ketones is
the C= O (carbonyl group).

Carboxylic Acids
 The functional group is a –COOH
 Carboxyl : Carbonyl + hydroxyl group.
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 Esters
 Derivative of a carboxylic acid in which the H of
the carboxyl group is replaced by a carbon group.

Amines (-NH2)
 The functional group is an amino group.
 Amines are classified as primary (1°) , secondary
(2°) or tertiary (3°).

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 Hydrocarbon

Aliphatic Aromatic

Alkanes

Cycloalkanes

Alkenes

Alkynes

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 1. Hydrocarbons

Organic compounds that are composed of only carbon

and hydrogen.
Examples : alkanes, alkenes, alkyne and arenes.
A saturated hydrocarbon contains only single bonds -
alkanes
An unsaturated hydrocarbon may contains double
bonds or triple bonds – alkenes and alkynes
Aromatic hydrocarbons, also commonly known as
arenes – unsaturated hydrocarbon.
Arenes are compounds which contain benzene or
benzene-like ring and have the chemical properties
characteristic of benzene.

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 Alkanes
 General formula for alkanes - CnH2n+2 , n ≥ 1
 Nomenclature (IUPAC System)
Eg: methane, ethane, propane…….

 Condensed formula

CH3CH2CH2CH3

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 IUPAC System
1. The longest chain of carbon atoms is taken as the
parent chain.
2. Each substituent is given a name and a number. The
number shows the carbon atom of the parent chain
to which the substituent is bonded.
3. If there is one substituent, number the parent chain
from the end that gives it the lower number.
4. If the same substituent appears more than once,
number the parent chain from the end that gives the
lower number to the substituent encountered first.
5. If there are two or more different substituents, list
them in alphabetical order.

Use hyphens to separate numbers from

Organic words
Chemistry and commas to separate numbers
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 The name of a hydrocarbon has three portions:

PREFIX + ROOT + SUFFIX

Identifies a group
attached to the main Tells the number of Tells the type of
chain and the C atoms in the organic
number of the molecule (the compound the
carbon to which it is longest and molecule
attached continuous) represents
 have –yl as their (functional
ending group)
PREFIX = PENDANT + LOCATION 9
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 Example: Roots No. of C
atoms
4 3 2 1 meth- 1
eth- 2
prop- 3
2-methyl but ane but- 4
Is the PREFIX pent- 5
A1C hex- 6
branch is Is the ROOT Is the SUFFIX
hept- 7
attached to  The main  The
oct- 8
C – 2 of the chain has 4 C compound is
non- 9
main chain atoms an alkane
dec- 10

10
PREFIX + ROOTOrganic
+ Chemistry
SUFFIX by: Mohamed
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 Density [g·cm3] (at
Alkane Formula Boiling point [°C] Melting point [°C]
20°C)
Methane CH4 -162 -183 gas
Ethane C2H6 -89 -172 gas
Propane C3H8 -42 -188 gas
Butane C4H10 0 -138 gas

Pentane C5H12 36 -130 0.626(liquid)

Hexane C6H14 69 -95 0.659(liquid)

Heptane C7H16 98 -91 0.684(liquid)

Octane C8H18 126 -57 0.703(liquid)

Nonane C9H20 151 -54 0.718(liquid)

Decane C10H22 174 -30 0.730(liquid)

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 Cycloalkanes
• Alkanes whose carbon atoms are joined in rings

• General formula for cycloalkanes - CnH2n , n ≥ 3

• Eg: cyclopropane, cyclobutane, cyclopentane, cyclohexane

Cyclopropane Cyclobutane

Cyclopentane
Cyclohexane
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 Physical properties
 The b.p of straight chain alkanes increase steadily with
relative molecular mass. The increase in b.p is due to the
increasing forces of attraction between molecules of
increasing size.
 Effect of branching on b.p
◦ A branched chain alkane boils at lower temperature than the
straight chain alkane with the same number of carbon atoms.
◦ This is because the branched chain alkanes are more compact
and have smaller surface area, smaller van der Waals forces =
low b.p
 Comparing the b.p of alkanes and cycloalkanes.
◦ The b.p of cycloalkanes are 10 - 15°C higher than the
corresponding straight chain.

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 Alkenes

• Contain at least one carbon-carbon double

bond.
• General formula for alkenes – CnH2n , n ≥ 2
– Eg: CH2=CH2
• The cis-, trans- system

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 Nomenclature
• Identify and name the parent hydrocarbon
• Number the carbon atoms in the main chain
• When the carbon chain contains more than 3
carbon atoms, a number is used to indicate
the position of ‘=‘
• Indicate the positions of the double bond and
the substituent.

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 Contain at least one carbon-carbon triple bond.
 General formula for alkynes – CnH2n-2 , n ≥ 2
 Eg: 1-butyne, 2-butyne

H2
HC C C CH3 H3 C C C CH3
But-1-yne But-2-yne

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  A hydrocarbon that contains hydroxyl group, -OH
 SUFFIX end with – ol
 Alcohol with the –OH group attached to the end carbon atom
is commonly called propyl alcohol or 1-propanol
 The PREFIX 1-indicates that the –OH groups is on the first or
end of C atom.
 The alcohol with the –OH group attached to the middle carbon
atom is commonly called isopropyl alcohol or 2-propanol
 The PREFIX 2-indicates that the –OH groups is on the second C
atom from the end.

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• Example:
1-propanol

2-propanol

• Alcohols, R-OH
• R is the alkyl group
• -OH is the functional group

methanol ethanol 1-propanol

(methyl alcohol) (ethyl alcohol) (propyl alcohol) 2-propanol
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(propyl alcohol)
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 Carbonyl compounds
 Aldehyde and ketones are carbonyl compounds
because they contain the carbonyl group, C=O
 In the carbonyl group, the carbon and oxygen
atoms are joined together by a double bond.
 Thus, the C=O bond consists of a sigma and a pi
bond.
 Aldehydes and ketones have the same
molecular formula, CnH2nO.
 The general formula of aliphatic aldehydes and
ketones are shown below.
 R and R’ may be alkyl or aryl groups.

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 Nomenclature

Aliphatic aldehydes

 The rules for naming aldehydes are similar to

those for naming alkanes, except that the final ‘e’
of the corresponding alkane name is dropped
and replaces by the suffix ‘al’.
 The carbon of the aldehyde group is counted as
part of the carbon chain.
 Thus, aldehyde with the formula CH3CHO is called
ethanal.

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 Example:

2,2-dimethylbutanal

4-phenylpentanal

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 Nomenclature of Ketones
 The rules for naming ketone are similar to those for
naming alkanes, except that the final ‘e’ of the
corresponding alkane name is dropped and replaces by
the suffix ‘one’.
 The carbon of the ketone group is counted as part of
the carbon chain.
 When naming the carbon atoms, the carbonyl group is
given preference over any substituents.

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 Example:

2-propanone

2-methyl-4-phenyl-3-pentanone

4-penten-2-one alphabetical order

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 Carboxylic Acids
• term “carboxylic” is derived from “carbonyl” and “hydroxyl”.

• carboxylic acid also contain carbonyl group, C=O in its

structure
O
C OH

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Nomenclature

• count number of carbons in the longest carbon chain

containing the – COOH group
• replace the –e with the suffix –oic acid
• compound containing multiple -COOH groups do not
drop the –e but add a di- or tri- to the ending – carboxylic acid
or add a di- or tri- to the suffix –oic acid.
Structural O O O O
Formula CH3 C OH CH3 CH2 C OH HO C CH2 C OH

Condensed
Structural CH3COOH CH3CH2COOH HOOCCH2COOH
Formula
IUPAC ethanoic acid propanoic acid propandioic acid

Common Name acetic acid - malonic acid

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 Esters
• to create an ester, an alcohol is reacted with a carboxylic acid
• an ester is named for its starting materials, the acid and the
alcohol
• the first part names the alcohol, use the side chain
abbreviation, i.e. methyl, ethyl…
• the second part names the carboxylic acid
• to end the second part change the –ic of the carboxylic acid to
-ate
O
Structural O O
CH3 C O CH3 CH3 CH2 C O CH2 CH3 CH3 C O
Formula
Condensed
Structural CH3COOCH3 CH3CH2COOCH2CH3 CH3COOC6H5
Formula
methyl
IUPAC ethyl propanoate phenyl ethanoate
ethanoate
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Common
12/13/2018 Name methyl acetate ethyl propyrate
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phenyl acetate 26