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Chapter 11

Organic Chemistry

The study of the compounds of carbon

Chapter 11 Organic Chemistry The study of the compounds of carbon

Some Properties Typical of Organic Compounds

Organic compounds form covalent bonds have low melting points and boiling points tend to be flammable are soluble in non-polar solvents are not very soluble in water

A Review of the Bonding in Carbon

not very soluble in water A Review of the Bonding in Carbon Oil and water Compounds

Oil and water

Compounds of Carbon and Hydrogen

Carbon has 4 valence electrons, and hydrogen has 1; to achieve an octet, C forms four bonds

We will use a line

to indicate the sharing

of 2 electrons

and hydrogen has 1; to achieve an octet, C forms four bonds We will use a
and hydrogen has 1; to achieve an octet, C forms four bonds We will use a

The bonding environment of carbon:

Type of bonds

Geometry of carbon

4

single bonds

tetrahedral geometry

2

single bonds + 1 double bond

triangular at carbon

1

single bond + 1 triple bond

linear at carbon

2

double bonds

linear at carbon

You may recall that when 4 groups are attached to a central atom, the groups arrange themselves so they point to the corners of a tetrahedron

themselves so they point to the corners of a tetrahedron The following illustrates 4 different but

The following illustrates 4 different but equivalent ways of illustrating the structure of methane:

Compound solely of carbon and hydrogen are called hydrocarbons;

if more than on carbon atom is present, then the molecule must have carbon- carbon bonds. The molecule shown below is called ethane

have carbon- carbon bonds. The molecule shown below is called ethane CH 3 CH 3 different

If carbon can form stable bonds to itself, there is no reason why there can’t be hydrocarbon composed of more than 2 carbons

can form stable bonds to itself, there is no reason why there can’t be hydrocarbon composed
can form stable bonds to itself, there is no reason why there can’t be hydrocarbon composed
can form stable bonds to itself, there is no reason why there can’t be hydrocarbon composed
Butane (butane lighter) has the following structures: Although the two forms of butane shown differ
Butane (butane lighter) has the following structures: Although the two forms of butane shown differ
Butane (butane lighter) has the following structures: Although the two forms of butane shown differ

Butane (butane lighter) has the following structures:

Although the two forms of butane shown differ in the orientation of the CH 3 groups circled, rotation of the groups as shown occurs quite rapidly

Butane, C 4 H 10 has one other feature worth describing.

In the structure shown above, each carbon is either attached to one or two other carbon atoms. Consider a different way in which these four carbon atoms can be attached

The lower molecule is called isobutane

If we consider hydrocarbons with 5 carbons, you can imagine a number of ways of putting the carbon backbone together

a number of ways of putting the carbon backbone together C – C – C CH
a number of ways of putting the carbon backbone together C – C – C CH

C – C – C

ways of putting the carbon backbone together C – C – C CH 3 -CH 2
ways of putting the carbon backbone together C – C – C CH 3 -CH 2

CH 3 -CH 2 -CH 2 -CH 2 -CH 3

C – C – C CH 3 -CH 2 -CH 2 -CH 2 -CH 3 All

All of these compounds have a molecular formula of C 5 H 12 are referred to as structural isomers. All are known compounds

Structural isomers have similar but different properties and can be distinguished from one another by identifying carbon atoms that have different number of carbon atoms attached

Are these structural isomers?

These are two different ways of drawing the same compound

CH 3 CH 3 CH CH 2 CH 3 CH 3 CH 2 HC CH
CH 3
CH 3
CH
CH 2
CH 3
CH 3
CH 2
HC
CH 3

CH 3

butane
butane

Some different ways of writing butane; all of then refer to the same compound because of rotation about the carbon-carbon bonds

A systematic way of naming alkanes and identifying identical structures

1. Locate the longest carbon chain in the molecule: this identifies the parent alkane

the longest carbon chain is 4:

butane

2. Identify the points of branching and count the number of carbons in each branch

2 points of branching at the same carbon: each 1 carbon

3. Name the branch on the basis of the number of carbons by dropping

the ane of the parent and adding yl:

methane

the ane of the parent and adding yl: m e t h a n e CH
CH 3 CH 3 C CH 2 CH 3 CH 3
CH 3
CH 3
C
CH 2
CH 3
CH 3
CH CH 2 3 CH C CH 3 3
CH
CH 2
3
CH
C
CH 3
3

methyl

CH 3

4. Give the first branch encountered the lowest number and use the prefix di,

tri, tetra,

for multiple groups

2 methyl groups both at carbon 2

lowest number and use the prefix di, tri, tetra, for multiple groups 2 methyl groups both

2,2-dimethylbutane

Name the following:

Name the following: Cl as a group is named chloro parent: groups position of groups hexane
Name the following: Cl as a group is named chloro parent: groups position of groups hexane

Cl as a group is named chloro

parent:

groups position of groups

hexane both methyl 2 at carbons 2 and 4

2,4-dimethylhexane

parent:

groups position of groups

heptane 2 chlorines and methyl chlorine at positions 3 and 5, methyl at position 3

3,5-dichloro-3 methylheptane

groups heptane 2 chlorines and methyl chlorine at positions 3 and 5, methyl at position 3
Name this compound: longest carbon chain groups: l o c a t i o n

Name this compound:

Name this compound: longest carbon chain groups: l o c a t i o n :

longest carbon chain

groups:

location:

5, pentane

chloro, methyl

CH 3 at C 2 and Cl at C 3

3-chloro-2-methylpentane

CH 3 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH-CH 2 -CH 2 -CH 3

CH 2 CH 3

longest carbon chain

10, decane

groups:

ethyl

4-ethyldecane

What is a general molecular formula for these alkanes? if n = the number of

What is a general molecular formula for these alkanes?

if n = the number of carbon atoms, note that the number of hydrogens is?

2n+2

The general formula for all the compounds is given by C n H 2n+2

2n+2 The general formula for all the compounds is given by C n H 2 n

How many C? How many H?

8

18

2*8+2 = 18

Can we make an alkane with n C but less the 2n+2 hydrogens? cycloalkanes can have less the (2n+2) H’s

C 5 H 10 C 6 H 12
C 5 H 10
C 6 H 12

H-CH 2 CH 2 CH 2 CH 2 -H

.

C 3 H 6 C 4 H 8
C 3 H 6
C 4 H 8
≡ H H CH 2 -CH 3 CH   CH 2 CH CH 2 2

H

H

CH 2 -CH 3

CH

 

CH 2

CH

CH 2

2 C

2 C

parent: cyclohexane

groups: ethyl, chloro

location: 1, 3

Cl 1-chloro-3-ethylcyclohexane

1-ethyl-3-chlorocylohexane

The textbook often draws hydrocarbons without all of the hydrogen shown. This is an abbreviated way of drawing the molecule. Please remember that carbon always has 4 bonds to it and if all the bonds are not designated, you need to assume there are hydrogens at these positions

you ne ed to assume there are hydrogens at these positions CH 3 CH C H

CH 3

CH

CH 3

parent:

cyclopentane

groups:

isopropyl

isopropylcyclopentane

Properties of n-alkanes

The properties of alkanes include being nonpolar insoluble in water less dense than water flammable in air

Alkanes with 1–4 carbon atoms are methane, ethane, propane, and butane all are gases at room temperature all are used as heating fuels

are gases at room temperature all are used as heating fuels Alkanes with 5–8 carbon atoms

Alkanes with 5–8 carbon atoms are liquids at room temperature all are very volatile all are found in gasoline

Alkanes with 9–17 carbon atoms are liquids at room temperature all have higher boiling points all are found in kerosene, diesel, and jet fuels

Alkanes with 18 or more carbon atoms are waxy solids at room temperature are used in waxy coatings of fruits and vegetables

with 18 or more carbon atoms are waxy solids at room temperature are used in waxy

The hydrocarbons in crude oil are often cracked to produce smaller hydrocarbons which are separated by their different boiling points

which are separated by their different boiling points All hydrocarbons can be burned in oxygen to

All hydrocarbons can be burned in oxygen to produce carbon dioxide and water

O

O

2

2

=

CO 2

= 8CO 2

+

C 8 H 18 + C 8 H 18 +

C 8 H 18 + 25/2O 2 = 8CO 2 + 9H 2 O + Heat

2C 8 H 18 + 25O 2 = 16CO 2 +18H 2 O + Heat

H 2 O + Heat

+ 9H 2 O + Heat

Compounds of carbon with other elements

Oxygen

oxygen has 6 valence electrons; needs to form 2 bonds

Oxygen oxygen has 6 valence electrons; needs to form 2 bonds If a molecule contains a

If a molecule contains a hydroxyl (–OH) group, it is called an alcohol.

ethyl alcohol, ethanol hydroxyethane

The the oxygen atom is bonded to two carbon atoms it is called an ether (–C–O–C–) .

In both these cases, the oxygen is single bonded to carbon

O

O

Compounds of carbon with other elements

Nitrogen

nitrogen has 5 valence electrons; needs to form 3 bonds

nitrogen has 5 valence electrons; needs to form 3 bonds In an amine, nitrogen is attached

In an amine, nitrogen is attached by a single bond to 1, 2, or 3 different carbon atoms

2 carbons
2 carbons

N

A Summary of the typical functional groups encountered in organic chemistry

Functional groups are a characteristic feature of organic molecules that behave in a predictable way are composed of an atom or group of atoms are groups that replace a H in the corresponding alkane provide a way to classify families of organic compounds

of atoms are groups that replace a H in the corresponding alkane provide a way to
of atoms are groups that replace a H in the corresponding alkane provide a way to
of atoms are groups that replace a H in the corresponding alkane provide a way to
of atoms are groups that replace a H in the corresponding alkane provide a way to
of atoms are groups that replace a H in the corresponding alkane provide a way to
of atoms are groups that replace a H in the corresponding alkane provide a way to
of atoms are groups that replace a H in the corresponding alkane provide a way to
of atoms are groups that replace a H in the corresponding alkane provide a way to
of atoms are groups that replace a H in the corresponding alkane provide a way to