Introduction

 Organic compounds contain not only C-C

bonds but also C-H bonds.

 C-C and C-H bonds tend to be non-polar

because there is a small difference in
electronegativites

 Most (but not all) organic compounds are

relatively non-polar
generally not very soluble in water

1 of 73
 Introduction
 Organic compounds that are soluble in polar
solvents such as water generally have a
polar functional group present in the
molecule.
An atom or group of atoms that
influences the way the molecule
functions, reacts or behaves.
an atom or group of atoms in a molecule
that undergoes predictable chemical
reactions
the center of reactivity in an organic
molecule
2 of 73
 GUGUS FUNSIONAL

Atom atau gugus atom yang

merupakan bagian dari senyawa
organik dan memberikan sifat-sifat
yang khas dari senyawa tersebut

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 Introduction
 Functional groups that contain O or N
atoms often lead to a polar organic
molecule
large difference in electronegativity
C vs. O
C vs. N
 Examples of familiar polar organic
compounds:
glucose Functional groups
acetic acid contain C-O bonds
Vitamin C Functional groups contain
amino acids C-O and C-N bonds 4 of 73
 Gugus fungsional yang pada
senyawa organik

Gugus Alkil (-R) memberikan sifat

yang khas pada senyawa hidrokarbon
Gugus Halida (-X) memberikan sifat
yang khas pada senyawa halida
Gugus Hidroksi (–OH) memberikan
sifat yang khas pada senyawa alkohol
dan fenol

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 Gugus fungsional yang pada
senyawa organik

Gugus Karbonil ( C=O)

6 of 73
7 of 73
 Functional Groups
Since functional groups are
responsible for the many of the
chemical and physical properties of
organic compounds, we often
classify and study organic
compounds by the type of functional
group present.

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 Functional Groups

Functional Type of
Group Compound Example
C=C alkene H2C = CH2
C C alkyne HC CH
C–O–H alcohol CH3OH
C–O–C ether CH3CH2OCH2CH3
C–N amine CH3NHCH3

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 Functional Groups

Functional Type of
Group Compound Example

O O

C–H aldehyde CH3C – H

O O

C–C–C ketone CH3 – C – CH3

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 Functional Groups

Functional Type of
Group Compound Example
O O
Carboxylic
C–O–H acid CH3C – O – H

O O

C–O–C ester CH3C – O – CH2CH3

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 Functional Groups

Functional Type of
Group Compound Example
O O

C–N– amide CH3C – N – CH3

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GAMES

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 Functional Groups

A CH3CH2OH D
O

B H2C = CHCOH

C CH3CNCH3 E
CH3
14 of 73
 Hydrocarbons
 The simplest organic compounds are the
hydrocarbons:
organic compounds that contain only
carbon and hydrogen

four general types:

alkanes
alkenes
alkynes
aromatic hydrocarbons

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Penggolongan Hidrokarbon

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 Hydrocarbons
 Alkanes:
hydrocarbons that contain only single
bonds

 Examples:
Methane CH4

ethane H H
H – C – C – H
H H
17 of 73
 Hydrocarbons
 Alkenes:
hydrocarbons that contain a C = C double
bond

H2C = CH2 (ethylene)

 Alkynes:
hydrocarbons that contain a C C triple
bond
H – C C – H (acetylene)

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 Hydrocarbons
 Aromatic hydrocarbons:
contain a planar ring structure in which
the carbon atoms are connected by a
combination of both s and p bonds
H
C
H - C -
C H benzene
H - C -
C C H
H
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 Hydrocarbons
 Alkanes are often called saturated
hydrocarbons
they contain the largest possible number
of hydrogen atoms per carbon atom.

 Alkenes, alkynes, and aromatic

hydrocarbons are called unsaturated
hydrocarbons
they contain less hydrogen than an
alkane having the same number of carbon
atoms
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 H H H H
Alkanes H C C C C H
H H H H
 Organic compounds can be
H represented
H H H in
many different ways:
H C C C C H
H H H
molecular formula: C4H10
H
H(butane)
H H H
Lewis structure: H
H H CH HC C C H
H C C C C H
H HH H HH H H
Condensed structural formula
 CH3CH2CH2CH3
Line angle drawings

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 Alkanes
Some of the simplest alkanes:
Condensed
Formula Name
CH4 methane
CH3CH3 ethane
CH3CH2CH3 propane
CH3CH2CH2CH3 butane
CH3CH2CH2CH2CH3 pentane

You must know these!!! 22 of 73

 Alkanes
Some of the simplest alkanes:
Condensed
Formula Name
CH3CH2CH2CH2CH2CH3 hexane
CH3CH2CH2CH2CH2CH2CH3 heptane
CH3CH2CH2CH2CH2CH2CH2CH3 octane
CH3CH2CH2CH2CH2CH2CH2CH2CH3 nonane
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3 decane
You must know these!!!
23 of 73
 Alkanes
 The previous alkanes are also called
straight-chain hydrocarbons:
all of the carbon atoms are joined in a
continuous chain

 Alkanes containing 4 or more carbons can

also form branched-chain hydrocarbons
(branched hydrocarbons)
some of the carbon atoms form a
“branch” or side-chain off of the main
chain
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 Alkanes
 An example of a straight chain hydrocarbon:

C5H12 CH3CH2CH2CH2CH3 pentane

 Examples of a branched hydrocarbon:

C5H12 CH3CHCH2CH3 CH3

CH3 CH3CCH3
2-methylbutane
CH3
2,2-dimethylpropane
25 of 73
 Alkanes
 The three structures shown previously for
C5H12 are structural isomers:
compounds with the same molecular
formula but different bonding
arrangements

 Structural isomers generally have different

properties:
different melting points
different boiling points
often different chemical reactivity
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 Alkanes
 Alkanes with three or more carbons can
also form rings or cycles.

 Cycloalkanes:
Alkanes containing a ring structure that
is held together by C – C single bonds

 Examples: CH2
H2C CH2
cyclopropane
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 Alkanes
 Examples of cycloalkanes:
CH2
H2C CH2 cyclopentane

H2C CH2

CH2
H2C CH2
cyclohexane
H2C CH2
CH2
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29 of 73
 Alkanes
 Organic compounds can be named either
using common names or IUPAC names.

 You must be able to name alkanes, alkenes,

alkynes, and alcohols with 10 or fewer
carbons in the main chain using the IUPAC
naming system.

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 Alkanes
 Alkane Nomenclature:
Find the longest continuous chain of
carbon atoms and use the name of the
chain for the base name of the
compound:
longest chain may not always be
written in a straight line
Base name:
1
CH3 -2 CH - CH3 hexane
3 4 6
5
CH2 - CH2 - CH2 - CH3

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 Alkanes
 Alkane Nomenclature:
Number the carbon atoms in the longest
chain beginning with the end of the chain
closest to a substituent
groups attached to the main chain
that have taken the place of a
hydrogen atom on the main chain

1
CH3 -2 CH - CH3 A substituent

CH2 - CH2 - CH2 - CH3

3 4 5 6
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 Alkanes
 Alkane Nomenclature:
Name and give the location of each
substituent group
A substituent group that is formed by
removing an H atom from an alkane is
called an alkyl group:

Name alkyl groups by dropping the “ane”

ending of the parent alkane and adding
“yl”

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 Alkanes
 Alkane Nomenclature:
Common alkyl groups (substituents):

CH3 methyl
CH3CH2 ethyl Know
CH3CH2CH2 propyl these!
CH3CH2CH2CH2 butyl

1
CH3 -2 CH - CH3
2-methylhexane
3 CH2 - CH2 - CH2 -
4 5 6
CH3
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35 of 73
36 of 73
 Alkanes
 Alkane Nomenclature:

Halogen atoms are another common class

of substituents.
Name halogen substituents as “halo”:
Cl chloro
Br bromo
I iodo

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 Alkanes
 Alkane Nomenclature:
When two or more substituents are
present, list them in alphabetical order:
 Butyl vs. ethyl vs. methyl vs. propyl

When more than one of the same

substituent is present (i.e. two methyl
groups), use prefixes to indicate the
number:
 Di = two Know these.
 Tri = three
 Tetra = four
 Penta = five
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 Alkanes
Example: Name the following compounds:

CH3CH2CHCH2CH3 3-metilpentana
CH3

CH2CH2CH3
CH3CHCHCH3 2,3-dimetilhexane

CH3
39 of 73
 Alkanes
Example: Name the following compounds:

CH3CH2CHCH3
1-bromo-3-metilpentana
CH2CH2Br

CH2CH2CH3 2-kloro-3-metilheksana
CH3CHCHCH3
Cl
40 of 73
 Alkanes
 You must also be able to write the
structure of an alkane when given the
IUPAC name.

 To do so:
Identify the main chain and draw the
carbons in it
Identify the substituents (type and #)
and attach them to the appropriate
carbon atoms on the main chain.
Add hydrogen atoms to the carbons to
make a total of 4 bonds to each carbon
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 Alkanes
Example: Write the condensed structure for
the following compounds:

3, 3-dimethylpentane

3-ethyl-2-methylhexane

2-methyl-4-propyloctane

1, 2-dichloro-3-methylheptane

42 of 73
 Alkenes
 Alkenes:
unsaturated hydrocarbons that contain a
C=C double bond

 Alkene Nomenclature:
Names of alkenes are based on the
longest continuous chain of carbon atoms
that contains the double bond.

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 Alkenes
 Alkene Nomenclature
Find the longest continuous carbon chain
containing the double bond.

Change the “ane” ending from the

corresponding alkane to “ene”
 butane butene
 propane propene
 octane octene

44 of 73
 Alkenes
 Alkene Nomenclature
Indicate the location of the double bond
using a prefix number
designate the carbon atom that is part
of the double bond AND nearest to
the end of the chain
Number the C atoms of the chain to
place the multiple bond at the lowest
possible number
Name all other substituents in a manner
similar to the alkanes.
Use a prefix to indicate the geometric
isomer present, if necessary. 45 of 73
 Alkenes
 Alkene Nomenclature

 Different geometric isomers are possible

for many alkenes.
Compounds that have the same molecular
formula and the same groups bonded to
each other, but different spatial
arrangements of the groups

cis isomer
trans isomer
46 of 73
 Alkenes
 Alkene Nomenclature
Cis isomer:
two identical groups (on adjacent
carbons) on the same side of the C =
C double bond

Trans isomer:
two identical groups (on adjacent
carbons) on opposite sides of the C =
C double bond

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 Alkene

CH3 CH3 CH3 H

C = C C = C
H H H CH3
cis-2-butene trans-2-butene

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 Alkene
For an alkene with the general formula
A P
C = C
B Q
cis and trans isomers are possible only if
A = B and
P = Q

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Naming the Stereoisomers of Highly Substituted
Alkenes: The E,Z System of Nomenclature
 Alkenes
Example: Draw the structures for the
following compounds:

2-chloro-3-methyl-2-butene

trans-3, 4-dimethyl-2-pentene

cis-6-methyl-3-heptene

52 of 73
 Alkene
Example: Name the following alkenes:

CH3CH2 H
C = C
H H

CH3CH2 H
C = C
CH3CHCH2 CH2CH3

CH3
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GAMES

54 of 73
55 of 73
56 of 73
57 of 73
58 of 73
 Alkynes
 Alkynes:
unsaturated hydrocarbons that contain a
C C triple bond

 Alkyne Nomenclature:
Identify the longest continuous chain
containing the triple bond

To find the base name, change the

ending of the corresponding alkane from
“ane” to “yne”
59 of 73
 Alkynes
 Alkyne Nomenclature:
Use a number to designate the position
of the triple bond
number from the end of the chain
closest to the triple bond
just like with alkenes

Name substituents like you do with

alkanes and alkenes

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 Alkynes
Example: Name the following compounds:

CH3CH2C CCHCH3
CH2CH3

CH2CH2C CH
Cl

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 Alkynes
Example: Draw the following alkynes.

4-chloro-2-pentyne

3-propyl-1-hexyne
Characteristics of Aromatic Hydrocarbons
•Planar (flat) cyclic molecules.
•Conjugated п systems

August Kekulé (1829-1896) who proposed the

hexagonal ring structure for benzene in 1865.
His representation of this molecule is still
widely used.
Naming Aromatic Hydrocarbons
General Chemistry: Chapter 26
 SUBSTITUENTS

General Chemistry: Chapter 26

Name of the Following Compounds

m-tolilsiklohekasana/
2,6 dimetilanilina m-sikloheksanatoluena

p-bromobenzil klorida
Slid
Copyright © 2011
e 69
General Chemistry: Chapter 26 Pearson Canada
of
Inc.
75
Structure of Alcohols
 Structure of Alcohols

 Hydroxyl (-OH) functional group

 Oxygen is sp3 hybridized.

=>
71
 Classification
 Primary: carbon with –OH is bonded
to one other carbon.
 Secondary: carbon with –OH is
bonded to two other carbons.
 Tertiary: carbon with –OH is bonded
to three other carbons.
 Aromatic (phenol): -OH is bonded to
a benzene ring.
72

=>
 Classification

 General classifications of alcohols

based on substitution on C to which
OH is attached

73
Classify these:

CH3 CH3
CH3 CH CH2OH CH3 C OH
CH3

OH
OH CH3 CH CH2CH3 =>

74
 IUPAC Nomenclature

 Find the longest carbon chain containing the

carbon with the -OH group.
 Drop the from the alkane name, add -ol.
 Number the chain, starting from the end closest
to the -OH group.
 Number and name all substituents. =>

75
Name these:
CH3
OH
CH3 CH CH2OH
CH3 CH CH2CH3
2-methyl-1-propanol 2-butanol
2-methylpropan-1-ol butan-2-ol
OH
CH3
CH3 C OH
Br CH3
CH3

2-methyl-2-propanol 3-bromo-3-methylcyclohexanol
2-methylpropan-2-ol 3-bromo-3-methylcyclohexan-1-ol
=>
76
Unsaturated Alcohols
 Hydroxyl group takes precedence. Assign
that carbon the lowest number.
 Use alkene or alkyne name.

OH
CH2 CHCH2CHCH3

4-penten-2-ol

77
Naming Priority
 Acids  Alkenes
 Esters  Alkynes
 Aldehydes  Alkanes
 Ketones  Ethers
 Alcohols  Halides
 Amines

=>

78
Hydroxy Substituent

 When -OH is part of a higher priority class

of compound, it is named as hydroxy.
 Example:

OH
CH2CH2CH2COOH

4-hydroxybutanoic acid

79
Common Names
 Alcohol can be named as alkyl alcohol.
 Useful only for small alkyl groups.
 Examples:

CH3 OH
CH3 CH CH2OH CH3 CH CH2CH3

isobutyl alcohol sec-butyl alcohol

80
Naming Diols

 Two numbers are needed to locate

the two
-OH groups.
 Use -diol as suffix instead of -ol.

HO OH

hexane-1,6- diol
81

=>
Glycols

 1, 2 diols (vicinal diols) are called glycols.

 Common names for glycols use the name
of the alkene from which they were
made.
CH2CH2
CH2CH2CH3
OH OH
OH OH

ethane-1,2- diol propane-1,2- diol

ethylene glycol propylene glycol

 Naming Phenols
 -OH group is assumed to be on carbon
1.
 Forcommon names of disubstituted
phenols, use ortho- for 1,2; meta- for
1,3; and para- for 1,4.
 Methyl phenols are cresols.
OH
OH

H3C
Cl
3-chlorophenol 4-methylphenol
meta-chlorophenol para-cresol
Naming Phenols

84
Give the IUPAC names for
these compounds:

OH OH
HO

OH

OH

H3C CH3

85
Draw the following
structures:

2-Ethyl-2-buten-1-ol

1-Cyclohexen-1-ol

1,4-Pentanediol
86
SENYAWA GUGUS KARBONIL
Naming Priority
 Acids  Alkenes
 Esters  Alkynes
 Aldehydes  Alkanes
 Ketones  Ethers
 Alcohols  Halides
 Amines

=>

89
Ethers
 The Carbonyl Group
The carbonyl group consists of one
sigma bond formed by the overlap of
sp2 hybrid orbitals and one pi bond
formed
Aldehydes and Ketones
 Structure
 Thefunctional group of an aldehyde is a
carbonyl group bonded to an H atom and a
carbon atom.
 Thefunctional group of a ketone is a carbonyl
group bonded to two carbon atoms.
O O O
HCH CH3 CH CH3 CCH3
Methanal Ethanal Propanone
(Formaldehyde) (Acetaldehyde) (Acetone)
 Physical Properties
 Oxygen is more electronegative than
carbon (3.5 vs 2.5) and, therefore, a C=O
group is polar.
+ - +
C O –
C O C O
Polarity of More imp ortant
a carbonyl contributin g
group structu re

• Aldehydes and ketones are polar compounds and

interact in the pure state by dipole-dipole interaction.
• They have higher boiling points and are more
soluble in water than nonpolar compounds of
comparable molecular weight.
 Nomenclature
 IUPAC names:
 The parent chain is the longest chain that
contains the carbonyl group.
 For an aldehyde, change the suffix from -e
to -al.
 For an unsaturated aldehyde, change the
infix from -an- to -en-; the location of
the suffix determines the numbering
pattern.
 For a cyclic molecule in which -CHO is
bonded to the ring, add the suffix -
carbaldehyde.
 Nomenclature: Aldehydes
O O O
7 5 3 1
H H 8 6 4 2
H

3-Meth ylb utanal 2-Propen al (2E)-3,7-D imeth yl-2,6-octad ienal

(A crolein ) (Geran ial)

4 1
CHO HO CHO
Cyclopen tane- trans -4-Hyd roxycyclo-
carb aldehyde hexan ecarbald ehyde

 The IUPAC naming uses the common names

benzaldehyde, cinnamaldehyde, formaldehyde and
acetaldehyde.

CHO CHO
C6 H5

Benzaldehyde t rans-3-Phenyl-2-propenal
(Cinnamaldehyde)
 Nomenclature: Ketones
IUPAC names
 The parent alkane is the longest chain that
contains the carbonyl group.
 For a ketone, change the suffix -e to -one.
 Number the chain to give C=O the smaller
number.
 IUPAC uses the common names acetone,
acetophenone, and benzophenone.
O O O
O

Prop anone A cetophen on e Benzophen on e 1-Phenyl-1-pen tanone

(Aceton e)
Order of Precedence
For compounds containing more than one
functional group usually indicated by a suffix:
Esters

The distinctive aroma and flavor of oranges

are due in part to the ester octyl acetate,
CH3CO2CH2(CH2)6CH3
Amides
Amines
 Introduction
 Organic derivatives of ammonia
 Many are biologically active.

=>
104
 Structure of Amines
Nitrogen is sp3 hybridized with a lone pair of
electrons in an sp3 orbital.

105
 Classes of Amines

 Primary (1): one C-N bond, 2 N-H bonds.

 Secondary (2): two C-N bonds, 1 N-H bond.
 Tertiary (3): three C-N bonds, no N-H bond.
 Quaternary (4): four C-N bonds, nitrogen
has a + formal charge.

106
Classify:

CH3
N
CH3

N
H

CH3 _
Br
CH3 C NH2 +
CH3CH2 N CH2CH3
CH3 CH3
107
Common Names
Name the alkyl or aryl groups bonded to
nitrogen, then add suffix -amine.

(CH3CH2)2NCH3 NHCH3
diethylmethylamine
cyclopentylmethylamine

NH

Diphenylamine 108
 Amine as Substituent
 Ona molecule with a higher priority
functional group the amine is named as a
substituent.
OH
NH2CH2CH2CH2COOH
NHCH3
aminobutyric acid or
4-aminobutanoic acid

2-methylaminophenol
109
 IUPAC Names
 Name is based on longest carbon chain.
 -e of alkane is replaced with -amine.
 Substituents on nitrogen have N- prefix.

Br N(CH3)2
NH2CH2CH2CHCH2CH3 CH3CH2CHCH2CH2CH3

3-bromo-1-pentanamine N,N-dimethyl-3-hexanamine
 Aromatic Amines

Amino group is bonded to a benzene ring.

Parent compound is called aniline.
CH3 NH2
NH2 N
CH3
H3C

aniline N,N-dimethylaniline 4-methylaniline

or p-toluidine

=>
111
 Heterocyclic Amines

The nitrogen is assigned the number 1.

H
N N N N N CH3
H H Pyridine
aziridine
Pyrrolidine
Pyrrole 2-methylpyridine