LEARNING OBJECTIVES

Explain the terms organic compounds and

hydrocarbon List the properties of homologous series Write the general formulas alkanes Name small alkane compounds of sizes C1C10 and alkyl groups of sizes C1-C4 Explain the changes in physical states, boiling points and densities of alkanes when sizes is increasing Write the combustion and replacement reactions of alkanes in the form of chemical equations Define the terms structural isomers

An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. Organic compounds may be classified between natural and synthetic compounds. Natural compounds refer to those that are produced by plants or animals. Sugars carbohydrates, enzymes, hormones, Proteins vitamins and fats and oils
Synthetic compounds are prepared by reaction of

other compounds. Most polymers (plastics and rubbers)

Hydrocarbons are compounds composed entirely of carbon and hydrogen atoms bonded to each other by covalent bonds.

Saturated hydrocarbons have only single

bonds between carbon atoms.

Unsaturated hydrocarbons contain a double

or triple bond between two carbon atoms.

Aromatic hydrocarbons

include benzene and all compounds resembling benzene.

carbon to carbon single bonds

Carbon to carbon Double bonds

carbon to carbon triple bonds

19.3

The majority of organic compounds are made from relatively few molecules: carbon, hydrogen, oxygen, nitrogen and the halogens.
hydrogen has 1 bond fluorine has 1 bond

H
F

(fluoro)
oxygen has 2 bonds

nitrogen has 3 bonds

bromine has 1 bond (bromo)

Br

chlorine has 1 bond (chloro)

Cl
I
C

iodine has 1 bond (iodo)

carbon has 4 bonds

11

Obeys Octet rule

The general formula of alkanes is CnH2n+2 E.g: n = 7 2 x 7 + 2 = 16 C7H16

 Alkanes are also known as saturated

hydrocarbons.
There are only single covalent bonds

between the carbon atoms of alkanes.

They are straight- or branched-chain

hydrocarbons

 Alkane molecules contain only

carbon-carbon and carbonhydrogen bonds.

14

Each carbon atom is joined to four

other atoms by covalent bonds. angles of 109.5o. nonpolar.

These bonds are separated by Alkane molecules are essentially

 The naming of organic compounds is now

done in accordance with the IUPAC system. Alkyl groups are used to name organic compounds. The general formula of an alkyl group is CnH2n+1. The corresponding alkane has the formula CnH2n+2

The letter R is often used in formulas to represent any of the possible alkyl groups.
16

R= CnH2n+1 (any alkyl group) R = CH3 methyl group R = CH3CH2 ethyl group

17

RULE 1. Select the longest continuous chain of carbon atoms as the parent compound.
Consider all alkyl groups attached to it as branch chains

or substituents that have replaced hydrogen atoms of the parent hydrocarbon. If two chains of equal length are found, use the chain that has the larger number of substituents attached to it. The alkanes name consists of the parent compounds name prefixed by the names of the alkyl groups attached to it.

This structure has 2 chains.

CH3

CH2

CH CH3

CH2

CH2

CH3

This chain has 6 carbon atoms.

19

This chain has 4 carbon atoms. 1 CH3 2 CH2 3 CH

CH2

CH2

CH3

CH3 4

20

This is the longest continuous chain. Select this chain as the parent compound.
1 2 3 4 5 6

CH3

CH2

CH CH3

CH2

CH2

CH3

21

1 CH3

2 CH2

3 CH

4 CH2

5 CH2

6 CH3

CH3 This is a methyl group.

It is a branch chain and can be considered to have replaced a hydrogen on the parent compound.
22

1 CH3

2 CH2

3 CH

4 CH2

5 CH2

6 CH3

CH3
The name of the compound3is 3methylhexane.
23

RULE 2. Number the carbon atoms in the parent carbon chain starting from the end closest to the first carbon atom that has an alkyl group substituted for a hydrogen atom.
If the first subsitutent from each end is on the

same-numbered carbon, go to the next substituent to determine which end of the the chain to start numbering.

This is the longest continuous chain for this structure.

Select this chain as the parent compound.

25

If the chain is numbered left to right, the isopropyl group is on carbon 5.

1 2

isopropyl group
26

Use right to left numbering so that the If the chain is numbered right to left, the isopropyl group is on carbonthe lowest group is on 4. isopropyl numbered carbon.
4-isopropyloctane 8 7 6 5 4 3 2 1

isopropyl group
27

Use right to left numbering so that the If the chain is numbered right to left the isopropyl group is on carbonthe lowest group is on 2. isopropyl numbered carbon.
2-isopropylpentane 5 4 3 2 1

isopropyl group
28

RULE 3. Name each alkyl group and designate its position on the parent carbon chain by a number (e.g., 2-methyl means group attached to C-2).
29

2-isopropyl pentane

RULE 4. When the same alkyl-group branch chain appears more than once, indicate this repetition by a prefix (di-, tri-, tetra- and so30 forth) written in front of the alkyl group name (e.g. dimethyl indicates two methyl groups).
The numbers indicating the alkyl-group positions are separated by a command and followed by a hyphen and are placed in front of the name (e.g., 2,3-dimethyl).

The methyl group appears twice

2,3-dimethylpentane

RULE 5. When several different alkyl groups are attached to the parent compound, list them in alphabetical order (e.g. ethyl before methyl in 3-ethyl-4methyloctane). Prefixes are not included in alphabetical ordering (ethyl comes before dimethyl).

Compounds with branches on the longest continuous chain of C atoms are named as derivatives of that chain.

The branches are named using the stem of the alkane having the same number of C atoms with the ending changed to -yl .
Thus, for the branched chain compound whose structural formula was just illustrated, the side chain CH3 is called methyl, and the three C continuous chain is called propane. Two, three or four identical side chains are named using the prefix di- , tri-or tetra-, respectively.

This is the longest continuous chain for this structure.

Since there are eight carbons in this chain, the compound is an octane. There are two alkyl groups attached to octane.

methyl

ethyl

3-ethyl-4-methyloctane

Ethyl is alphabetically before methyl. Name the ethyl group before the methyl group.
Use left to right numbering so that the ethyl group is on the lowest numbered carbon. The methyl group is then on carbon number 4.

37

38

CH4
There is 1 possible structure for CH4.
line structure form of methane space filling form of methane

H H C H H

CH3CH3

There is 1 possible structure for C2H6.

line structure form of ethane

H H H C C H H H

space filling form of ethane

CH3CH2CH3

There is 1 possible structure for C3H8. line structure form of propane

H H H H C C C H H H H

space filling form of propane

CH3CH2CH2CH3
There are 2 possible structures for C4H10 line structure form of butane

H H C H

H C H

H C H

H C H
unbranched chain

space filling form of butane

CH3 CH2CHCH3

There are 2 possible structures for C4H10.

H H H H C H H H H

line structure form of 2-methyl propane

branched chain

H C C C H

space filling form of 2-methyl propane

branched chain

normal butane (n-butane) C4H10

m.p. 0.5oC b.p. 138.3oC

H H H H H C C C C H H H H H
H H H H C H

m.p. 159.5oC b.p. -11.7oC

H C C C H H H H
2 methyl propane C4H10

Isomers are compounds with the same molecular formula but different structural formulas.

Normal butane and 2-methyl propane are isomers.

Pentane (C5H12) has 3 isomers.

carbon skeleton with the longest continuous carbon chain. It is the first isomer of pentane.
C C C C C

n-pentane
48

Hydrogen is added to each carbon to form four bonds.

H H H H H H C C C C C H H H H H H

n-pentane

Pentane (C5H12) has 3 isomers.

Add the fifth carbon atom to either of the middle carbon atoms.

C C C C C
2-methylbutane

50

To form the next isomer write a four carbon chain.

C C C C

Hydrogen is added to each carbon to form four bonds.

H H H C H H H C C C C H H H H H H

Pentane (C5H12) has 3 isomers.

Hydrogen is added to carbon Add the remaining twoeach To form the third isomer write a 3 atoms chain. four carbon carbonto the centralbonds. atom. to form
H H H C H C C C H H C H H H H 2,2-dimethylpropane H

H H H H

structural H C C C C H formula H H H H

condensed structural formula

CH3CH2CH2CH3

Alkenes
HC that has 1 Carbon-to-Carbon double bond

in each molecule.
General formula CnH2n 2 electrons involved as the second pair of the

double bond are not shared with hydrogen atoms, so each molecule of an alkenes has 2 fewer H atoms than that of the corresponding alkenes.
Said to be unsaturated Hydrocarbons

 The alkenes are named systematically:

Use the name of alkane having the same number of

carbon atoms and change the ending to ene

The location of double bond is indicated when

necessary. Of the 2 Carbon atoms involved in the double bond, use the address of the carbon closer to the nearer end of the longest chain in the name
1 2 3 4 5

CH3CH=CHCH2CH3

is 2-pentene

If the double bond is not in the longest continuous

chain, name the compound with a shorter chain including the double bond

CH3

CH2
1

C CH2 CH2

CH3

is 2-ethyl-1-butene
The names and formulas of the

first for unbranched alkenes are presented table 19.2 (appendix)

Alkynes
HC that has 1 Carbon-to-Carbon triple bond in each

molecule.
Formula: CnH2n-2
unsaturated Hydrocarbons

the ending to yne

Haloalkanes / Alkyl Halide

also known as halogenoalkanes or alkyl

halides. derived from alkanes containing one or more halogens (group 17-in periodic table).

Hydrocarbons
a class of HC whose molecules contain a

ring of 6 C atoms, each with only 1 H atom (or other group) attached, has special properties which is known as Aromatic Hydrocarbon.
The simplest member is benzene, and all

other members have at least 1 benzene ring included in their structures.

Alcohols
If a H atom on a HC is replaced by a

functional group consisting of covalently bonded oxygen and hydrogen ( OH) an alcohol are formed.
The systematic name of each alcohol is

formed from the name of the parent HC by changing the ending to -ol . eg: CH3CH2OH is ethanol

Carboxylic acids
contain a -COOH group

General formula:

Aldehydes and Ketones

Objectives:
Nomenclature of aldehyde and ketone Preparation of aldehyde and ketone Reaction of aldehyde and ketone

Introduction
O
Have functional group called carbonyl,

C
2 types of carbonyl compounds:

aldehydes & ketones.

General formula; CnH2nO

 Both aldehydes and ketones have a carbonyl group as

the functional group:

C Ketones have it somewhere other than the end.

Aldehydes have the carbonyl group of the end of a C

chain. The end C O atom also has the H atom attached C H

The systematic names of aldehydes end in -al and

ketones end in -one

O
HCHO or H C

O H
CH3COCH3 or CH
3

CH
3

Methanal (formaldehyde )

Propanone (acetone)

Aldehydes and ketones can be isomers of each other

because both have the general molecular formula CnH2nO

IUPAC nomenclature
ALDEHYDE
Aldehyde are named by using the suffix al.
As the carbonyl group is at the end of the carbon

chain, the carbonyl carbon is always labeled no. 1.

O H-C-H
methanal

O CH3-C-H
ethanal

O CH3CH2CH2C-H
butanal

O C-H
Benzaldehyde / phenylmethanal H CH3 4-methylpentanal O

O
CH2-C-H
2-phenylethanal

Cl CH3

CH3-C-CH2-CH2-C-H

CH3-C-CH2-C-H 3-chloro-3-methylbutanal

O O H-C-CH2-CH2-C-H
1,4-butandial

H-C=O

Cl
3-chlorobenzaldehyde

O
CH2-CH=CH-CH2-C-H
5-phenyl-3-pentenal

O O General structure of aldehyde is H-C-H or R-C-H O General structure of ketone is R-C-R.

Ketones
Are named by using the suffix ONE. The carbonyl carbon must be of lowest number

as the functional group is the highest priority. O CH3-C-CH3

propanone

O CH3-CH2-C-CH3
2-butanone

O CH3-CH2-CH2-C-CH3
2-pentanone / pentan-2-one

O CH3-CH2-C-CH2-CH3
3-pentanone / pentan-3-one

O CH3-CH-C-CH3

O
CH2-CH2-C-CH3
4-phenyl-2-butanone

CH3
3-methylbutanone