NFTF WEEK 1,2,3

1.0 Introduction To Organic Chemistry

1.1 Introduction To Organic Chemistry

a) Identify the elements that made up organic compounds: C, H, O, N, P, S and halogen.

Give structures of organic compounds such as methane, glucose, urea, DDT, penicillin, nicotine, caffeine and DNA.

b) Define hydrocarbon compounds.

1.2 Classification Of Organic Compounds

a) Define functional group.
b) Name functional groups.
c) Classify organic compounds according to their functional groups.

(Differentiate between functional groups and class of compounds)

d) Define homologous series and explain general characteristics of its members:

i. represented by a general formula

ii. same functional group and chemical properties

iii. gradual change in physical properties with increasing number of carbon atoms
iv. successive member of a series (differs by a − CH2 − unit)

e) State the ability of carbon to form 4 covalent bonds with other carbons or other elements.

i. single bond ii. double bond iii. triple bond

f) Differentiate between saturated and unsaturated organic compounds.

1.3 Structural Formula

a) Define structural formula.

b) Draw possible structural formulae based on molecular formula in the form of condensed
and expanded structures.

c) Explain primary (1o), secondary (2o), tertiary (3o) and quaternary (4o) carbons.

d) Classify and draw the constitutional isomers iii. functional group isomers
i. chain isomers ii. positional isomers

1.4 Basic Reactions In Organic Compounds ii. electrophiles iii. nucleophiles 1
State the type of reactions in organic:

i. free radicals

a) Identify the elements that made up organic
compounds: C, H, O, N, P, S and halogen.

Give structures of organic compounds such as
methane, glucose, urea, DDT, penicillin, nicotine,

caffeine and DNA.

b) Define hydrocarbon compounds.

2

Definition of organic compound:
-a compound consisting entirely
of hydrogen and carbon and additional elements
such as nitrogen, Sulphur, oxygen and halogen

In chemistry, an organic
compound is generally any

chemical compound that
contains carbon

Definition of hydrocarbon:
- a hydrocarbon is an organic compound consisting

entirely of hydrogen and carbon

3

Example of Structures of organic compounds.

Methane DDT

Nicotine
DNA

Urea

Peniciline 4

Caffeine

a) Define functional group.

b) Name functional groups.

c) Classify organic compounds according to their functional groups.

(Differentiate between functional groups and class of compounds)

d) Define homologous series and explain general characteristics of

its members:

i. represented by a general formula

ii. same functional group and chemical properties

iii. gradual change in physical properties with increasing number of

carbon atoms
iv. successive member of a series (differs by a − CH2 − unit)
e) State the ability of carbon to form 4 covalent bonds with other

carbons or other elements.

i. single bond ii. double bond iii. triple bond

f) Differentiate between saturated and unsaturated organic

compounds. 5

Definition:
The functional group is defined as an atom or group
of atoms joined in a specific manner, which gives the
chemical properties of the organic compound and

are the centers for chemical reactivity.

An atom or a group of atoms in a molecule that
primarily determines how the molecule reacts

The reactive part of the molecule

EXAMPLE: 2–propanol (alcohol)

CH3–CH–CH3

OH functional group: –OH
(reactive part)

The reaction happen here! 6

Example of reactions :

Functional CH3
CH3 group CH3 C Cl + H2O

CH3 C OH + HCl CH3
tert-butyl chloride
CH3
tert-butyl alcohol

CH3CH2—Cl + NaOH CH3CH2—OH + NaCl
ethyl chloride ethanol

Functional 7
group

IMPORTANCE OF FUNCTIONAL GROUP
It determines:

chemical reactivity : Compounds having a similar
functional group have undergone similar reactions.

bonding and shape
physical properties
nomenclature

8

Question : circle the functional group for the
organic compounds in the reaction below

Cl OH
+ NaOH + NaCl

chlorocyclohexane cyclohexanol

9

CLASS OF alkane
COMPOUND

FUNCTIONAL do not have a functional
GROUP group  contains only C–H and
STRUCTURE C–C (single bond)

SIMPLE Structure: CH3CH3
EXAMPLE Name: ethane

NAME –ane 10
ENDING

HHH pentane
H CCCH

HH H

propane

Alkanes have no polar bonds, no lone pairs,
and no p bonds

 So, it has no reactive sites
(no functional group)

11

C═C

CLASS OF alkene
COMPOUND
CC carbon–carbon
FUNCTIONAL double bond
GROUP
STRUCTURE Structure: CH2═CH2
Name: ethene (ethylene)
SIMPLE
EXAMPLE –ene 12

NAME
ENDING

C≡C

CLASS OF alkyne
COMPOUND
CC carbon–carbon
FUNCTIONAL triple bond
GROUP
STRUCTURE H–C≡C–H
ethyne (acethylene)
SIMPLE
EXAMPLE –yne 13

NAME
ENDING

aromatic ring

CLASS OF aromatic compounds
COMPOUND (arene)

FUNCTIONAL CH aromatic ring
GROUP HC CH
STRUCTURE C6H6 ; benzene
HC CH
SIMPLE CH
EXAMPLE
CH
NAME HC CH
ENDING
HC CH
CH

none 14

–X

CLASS OF alkyl halide (haloalkane)
COMPOUND
d+ d– halogens / halo
FUNCTIONAL ( X = F, Cl, Br, I )
GROUP CX
STRUCTURE
CH3– Cl 15
SIMPLE chloromethane
EXAMPLE
none
NAME
ENDING

–OH

CLASS OF alcohol
COMPOUND
Cd+ d– H hydroxyl
FUNCTIONAL
GROUP O
STRUCTURE
CH3–O–H
SIMPLE methanol
EXAMPLE
–ol
NAME
ENDING 16

–OR

CLASS OF ether
COMPOUND
d+ d– alkoxy
FUNCTIONAL
GROUP C OC
STRUCTURE
CH3–O–CH3
SIMPLE dimethyl ether
EXAMPLE
ether
NAME
ENDING 17

–NH2
–NHR
–NR2

CLASS OF amine
COMPOUND
d+ d– amino
FUNCTIONAL
GROUP CN
STRUCTURE
CH3–NH2 18
SIMPLE methylamine
EXAMPLE
–amine
NAME
ENDING

C═O

CLASS OF aldehyde C═O group at the end
COMPOUND of C chain

FUNCTIONAL d–O carbonyl
GROUP
STRUCTURE d+

C CH

SIMPLE O ethanal (acetaldehyde)
EXAMPLE CH3–C–H

NAME –al
ENDING 19

C═O

CLASS OF ketone C═O group between
COMPOUND two C atoms

FUNCTIONAL d– O carbonyl
GROUP
STRUCTURE d+

C CC

SIMPLE O
EXAMPLE
CH3–C–CH3 propanone (acetone)
NAME
ENDING –one 20

–COOH

CLASS OF carboxylic acid
COMPOUND
d– O carboxyl
FUNCTIONAL
GROUP d+
STRUCTURE
C C OH
SIMPLE
EXAMPLE O
CH3–C–OH
NAME ethanoic acid (acetic acid)
ENDING
–oic acid 21

–COOR

CLASS OF ester
COMPOUND
d –O carboalkoxy
FUNCTIONAL C COC
GROUP
STRUCTURE d+

SIMPLE O
EXAMPLE
CH3–C–O–CH3
NAME methyl ethanoate (methyl acetate)
ENDING
–oate 22

–CONH2,
–CONHR,
–CONR2

CLASS OF amide
COMPOUND
O d– carboxamide
FUNCTIONAL C CN
GROUP
STRUCTURE d+

SIMPLE O
EXAMPLE
CH3–C–NH2
NAME ethanamide (acetamide)
ENDING
–amide 23

–COCl

CLASS OF acid chloride (acyl chloride)
COMPOUND

FUNCTIONAL d– O
GROUP
STRUCTURE C C Cl

SIMPLE d+
EXAMPLE
O
NAME
ENDING CH3–C–Cl

ethanoyl chloride (acetyl chloride)

–oyl chloride 24

–COOCO–

CLASS OF acid anhydride O between two
COMPOUND C═O groups

FUNCTIONAL d– O O
GROUP
STRUCTURE C C O C C anhydride

d+

SIMPLE OO
EXAMPLE
CH3–C–O–C–CH3
NAME ethanoic anhydride (acetic anhydride)
ENDING
–oic anhydride 25

–C≡N

CLASS OF nitrile
COMPOUND
d+ d– cyano
FUNCTIONAL
GROUP C CN
STRUCTURE
CH3–C≡N 26
SIMPLE ethanenitrile (acetonitrile)
EXAMPLE
–nitrile
NAME
ENDING

H3C Cl
H3C C O

NH C

C

OH

Circle and name all class of
compounds and name the
functional group present in the

structure

27

HOMOLOGOUS SERIES

Definition:
A series of compounds where each member
differs from the next member by a constant unit
(CH2 group) is called homologous series.

Represented by a same general formula
Have same functional group

Have same chemical properties
The members are called homologs

Example : CH2

CH4 H3C CH3 H3C CH2 CH3
methane ethane CH3 H3C
2 CH2
1
propane butane

3 28

4

GENERAL FORMULA OF HOMOLOGOUS SERIES

SERIES GENERAL FORMULA ENDING NAME
ALKANE CnH2n+2 …ane
ALKENE CnH2n …ene
ALKYNE CnH2n-2 …yne
ALCOHOL R-OH …ol
ALDEHYDE RCHO …al
KETONE RCOR’ …one
CARBOXYLIC ACID RCOOH …oic acid
AMINE RNH2 …amine
AMIDE RCONH2 …amide

Note: R normally refer to alkyl group (carbon chain)
: CnH2n+1

Reduce 2 atom H for cyclic compound 29

Carbon is able to form 4 covalent bonds with other
carbon or elements

CH3 H3C

Carbon with H3C C CH3 H3C C OH
single bond CH3 CH3

Carbon with H3C CO
double bond C CH2 H3C

Carbon with H3C CH3
triple bond
H3C C CH H3C C N

30

Saturated and Unsaturated organic compounds

Compound Saturated organic Unsaturated organic
compounds compounds

Bonds Molecule contain only Molecule contain multiple
single bonds bonds

Class Alkane Alkenes, alkyne, aromatic
compound hydrocarbons

Number of Have maximum number Fewer than the maximum
number of hydrogen
hydrogen of hydrogen atom

HC CH alkyne H2C CH2 alkene

H3C CH3 H H
C C

Example HC

C C CH
H

H 31
aromatic hydrocarbons

a) Define structural formula.

b) Draw possible structural formulae based on

molecular formula in the form of condensed

and expanded structures.

c) Explain primary (1o), secondary (2o), tertiary(3o)

and quaternary (4o) carbons.

d) Classify and draw the constitutional isomers

i. chain isomers

ii. positional isomers 32
iii. functional group isomers

STRUCTURAL FORMULA

Definition:
A chemical formula showing the linkage of the
atoms in a molecule diagrammatically, as H–O–H

Shows the actual number of atoms, their
relative placement, and the bonds between them

EXAMPLE: H
HO H
C H
H CCCH H

HH H 33
propanone methane

Many ways to write structural formula:

Shows difference in connectivity of atoms
Expanded structure (dash formula)
Condensed structure
Skeletal structure (bond–line formula)

Shows how atoms are arranged in space (3–D)

Wedge–dashed wedge line formula

Fisher projection 34

EXPANDED STRUCTURE

Shows all covalent bonds between atoms

Not representation of actual shape of molecule

Example: Formula : C3H6

Formula : C3H8O HHH
H CCCH
HHH
H
12 3 propene (C3H6)

H CCCH

HO H

H
2–propanol

35

Write an expanded structure for each of the

following hydrocarbons:

a) propane, C3H8
b) propene, C3H6 (has one double bond)
c) propyne, C3H4 (has one triple bond)
d) cyclopropane, C3H6 (cyclic structure)

Write an expanded structure for each of the
following hydrocarbons:

a) butane, C4H10

b) pentane, C5H12

c) cyclobutane, C4H8 (cyclic structure)

d) cyclobutene, C4H6 (cyclic structure and

has one double bond) 36

CONDENSED STRUCTURE

C–H and C–C single bonds are normally not
shown

Draw a C with 3 H’s as CH3
Draw a C with 2 H’s as CH2

Example: propane (C3H8)

HHH CH3CH2CH3
H CCCH condensed structure

HH H 37

expanded structure

USE OF ( ) IN CONDENSED STRUCTURE

To show heteroatoms, functional groups,
alkyl groups, at the side chain

EXAMPLE: 2–propanol (C3H8O)

HHH CH3CHCH3 All are
H CCCH OH condensed
structures!
HO H CH3CH(OH)CH3
38
H CH3CHOHCH3

expanded structure (CH3)2CHOH

EXAMPLE: 2–methylpropane (C4H10)

HHH

H CCCH

H C H
H H

H

expanded structure

( ) are used around similar
groups bonded to same atom

(CH3)3C H 39
condensed structure

Write the structure properly (check the
connectivity of the atoms)

EXAMPLE: CH3CHCH3 CH3CHCH3
OH OH
CH3CHCH3
OH

correct

40

( ) also indicate repeating structures
EXAMPLE: Octane (C8H18)

HHHHHH H H
H CCCCCC C C H

HHHHHH H H

expanded structure

CH3CH2CH2CH2CH2CH2CH2CH3

or condensed structure

CH3(CH2)6CH3 41

For single atoms such as halogens  no need ( )

EXAMPLE: 2–chloropropane (C3H7Cl)

HHH CH3CHCH3 condensed
H CCCH Cl structure

H Cl H CH3CHClCH3
expanded structure
(CH3)2CHCl

42

CONDENSED STRUCTURES CONTAINING
C–O BOND

EXAMPLE:

condensed structure expanded structure
HO
CH3CHO
ethanal H C C H correct
H

H

H C C OH

H

43

EXAMPLE:

condensed structure expanded structure

CH3COCH3 HOH
propanone HCCCH

HH

correct

HH
HCCOCH

HH

44

EXAMPLE: expanded structure
HO
condensed structure
CH3COOH H CC OH
acetic acid H
correct

H
H CCO OH

H

45

EXAMPLE:

condensed structure expanded structure

CH3COOCH3 HO H
methyl acetate
H CCOCH

HH

correct

HH
H CCO OCH

HH

46

EXAMPLE:

condensed structure expanded structure

CH3CH2OCH3 HH H
ethyl methyl ether
H CCOCH

HH H

correct

HOH
H CCCH

HH

47

Condensed structures

The following examples also condensed
structures!

EXAMPLE:

CH3–CH–O–CH2–CH2–CH2–OH

CH3

O

CH3–CH–CH2–C–O–CH3

OH

48

CONDENSED STRUCTURES OF CYCLIC COMPOUNDS

The bonds connecting atoms that form the
ring structure and side groups must be shown

expanded structure condensed structure

HH CH2
H2C CH2
C
HH

CC

HH

H H H H2C CH2
H C HH H2C CH
CC CH3
C

HC

H HH 49

Condensed structures

When writing the structures, always

check the number of bonds attached to

each atom!

C  4 bonds O  2 bonds

H  1 bond halogens  1 bond

HHH O

F C C CH CH3OCH2CH3 CH3–C–CH3

H H C F
H

H CH2ClCH2CH2CH2OH

50