Hydrocarbons &

Functional Groups

O
Organic
chemistry
h
is the
h chemistry
h
off carbon.
b
Th name organic
The
i reflect
fl the
h ffact that
h organic
i
molecules are derived from living organisms.
organisms In
this unit will start by looking at four families of
organic molecules that are grouped together as
y
We will also look at some
the hydrocarbons.
ffunctional groups
g p that define
f
some off the other
families of organic molecules.

ORGANIC CHEMISTRY

Organic chemistry is the chemistry of carbon.

There are three forms of pure carbon

Diamond

Graphite
3

ORGANIC CHEMISTRY

Organic chemistry is the chemistry of carbon.

There are three forms of pure carbon

Buckminsterfullerene
Bucky Balls

HYDROCARBONS

Organic molecules contain carbon combined with

other elements.

Organic molecules are grouped into families

Members of a family
y share common structural,, p
physical,
y
, and
chemical characteristics.

There are four families that contain molecules made

off only
l carbon
b and
d hydrogen.
h d

Hydrocarbons

Alkanes

Alkenes

Alkynes

Aromatics

HYDROCARBONS

ALKANES

Alkanes are hydrocarbons that contain only

carbon-carbon
carbon
carbon single bonds.
Every carbon atom participates in 4 single bonds,
either to another carbon or to a hydrogen.
y
g
Every hydrogen atom is bonded to a carbon by a
single bond.

ALKANES

Alkanes are hydrocarbons that contain only

carbon-carbon
carbon
carbon single bonds.

ALKANES

Alkanes in which the carbons are connected in a

straight chain are called normal alkanes.
H

H C

n-hexane

Alkanes that are branched are called branched

chain alkanes.
H
H

H
H

H C

2-methyl
methyly -p
pentane
H

ALKANES

Alkanes, along with the other hydrocarbons, are nonpolar.

They
y interact with each other only
y through
g London
dispersion forces.

This is why they have relatively low boiling and

melting points.

10

ALKANES

They interact with each other only through

London dispersion forces.

Note how the boiling points increase with molecular

weight.
g

11

MOLECULE IN THE NEWS

12

MOLECULE IN THE NEWS:M

MELAMINE

13

ORGANIC MOLECULES IN THE NEWS!!

http://www.cbc.ca/health/story/2007/09/06/additives-lancet.html?ref=rss
p
y
http://www.medpagetoday.com/Psychiatry/ADHD-ADD/tb/6610

Quinoline yellow

Sodium benzoate

Carmoisine

14

ALKANES

Alkanes, cannot be named based on their

Alkanes
molecular formulas

For example,
example all of the molecules shown below share
the same molecular formula, C6H14
((hexacarbon tetradecahydride?)
y
)
H

H C

n-hexane
H
H

H C

H C

H C

H
H

H
H

2-methyl
methyl--pentane

3-methyl
methyl--pentane

2,2--dimethylbutane
2,2

H C

H
H

C
H

15

2,3--dimethylbutane
2,3

ALKANES

Organic chemists use a systematic set of rules,

called the IUPAC rules, to name organic
molecules based on their structural formulas
instead of their chemical formulas.
H

H C

n-hexane
H
H

H C

H C

H C

H
H

H
H

2-methyl
methyl--pentane

3-methyl
methyl--pentane

2,2--dimethylbutane
2,2

H C

H
H

C
H

16

2,3--dimethylbutane
2,3

CONSTITUTIONAL ISOMERS

When two or more molecules share the same

molecular formula, but have different atomic
connections, they are called constitutional
isomers.
H

H C

n-hexane
H
H

H C

H C

H C

H
H

H
H

2-methyl
methyl--pentane

3-methyl
methyl--pentane

2,2--dimethylbutane
2,2

H C

H
H

C
H

17

2,3--dimethylbutane
2,3

CONFORMATIONS

Carbon-carbon single bonds are free to rotate

This leads to different shapes for some molecules

These should not be confused with isomers.

18

CONFORMATIONS

All of the 3-dimensional models shown below are

for the n
n-butane.
butane.
They were generated by rotating the central carboncarbon bond.
They all share the same structural formula.

19

CONFORMATIONS

All of the 3-dimensional models shown below are

for the n
n-butane.
butane.

They were generated by rotating the central carboncarbon bond.

20

CONFORMATIONS

Switching from one conformation to another does

not require the breaking and making of covalent
bonds.

Switching from one isomer to another does require

the breaking and making of covalent bonds.
bonds

n-butane

2-methylpropane
H

H
H

H
H

21
H

CYCLOALKANES

When there are three or more carbons in a

straight chain, the ends can be joined to make
rings.

In naming these molecules, the prefix cyclo- is used

to indicate the ring:

Skeletal structural formulas are used to represent

the rings in structural formulas:

22

CYCLOALKANES

In naming these molecules, the prefix cyclo- is

used to indicate the ring.

23

CYCLOALKANES

As Parent Chain

As Substituent Group

C 3H 6

cyclopropane

cyclopropyl-

C 4H 8
cyclobutane

cyclobutyl-

cyclopentyl-

C 5 H 10
cyclopentane

C 6 H 12
cyclohexane
y

R
cyclohexylcyclohexyl

24

CYCLOALKANES

The carbon-carbon single bonds for the carbons in

a ring are no longer free to rotate.
This leads to a new type of isomer
Since the two structures share the same name,
name they
are not constitutional isomers.

25

CYCLOALKANES

CH3

CH3

CH3

1,2-dimethylcyclohexane
H
H

H
H

H
H
H

H
CH3

1,2-dimethylcyclohexane

H
H
H
CH3

CH3

H
CH3

H
H
H

H
H

CH3
26

CYCLOALKANES

IIsomers which
hi h share
h
the
th same atomic
t i connections,
ti
and
d
therefore, the same IUPAC name are called
ste eoiso e s
stereoisomers.
When this occurs due to restricted rotation about a covalent
b d th
bond,
they are called
ll d geometric
t i isomers
i
The prefix cis- and trans- are used to distinguish geometric
isomers.
isomers

27

CYCLOALKANES

CH3

CH3

CH3

cis-1,2-dimethylcyclohexane
H
H

H
H

H
H
H

H
CH3

trans-1,2-dimethylcyclohexane

H
H
H
CH3

CH3

H
CH3

H
H
H

H
H

CH3
28

QUESTIONS

Draw the condensed structural formulas for the

following molecules:

1-ethyl-2-methylcyclopentane

1,1-dimethylcyclobutane

1,1-dimethyl-2-propylcyclopropane

Do any of these molecules have cis

cis- and trans
transgeometric isomers?
29

ALKENES, ALKYNES & AROMATIC

COMPOUNDS

The remaining three families of hydrocarbons

are unsaturated.

Alkanes are saturated, which means they contain

the
h maximum
i
number
b off hydrogens
h d
per carbon.
b
For alkanes CnH(2n+2)
(
)

Alkenes, Alkynes and Aromatics are

unsaturated which means they contain less than
unsaturated,
the maximum number of hydrogens per carbon.
Structurally, this means that they have carbon-carbon double
or triple bonds
30

ALKENES, ALKYNES & AROMATIC

COMPOUNDS

Alkenes are hydrocarbons that contain at least 1

carbon-carbon
carbon
carbon double bond.

Examples:

H
C

H
C

ethene
(ethylene)

C
CH2 CH2 CH2 CH3
1-hexene

31

ALKENES, ALKYNES & AROMATIC

COMPOUNDS

Alkynes are hydrocarbons that contain at least 1

carbon-carbon
carbon
carbon triple bond.

Examples:

ethyne
(acetylene)

C CH2 CH2 CH2 CH3

1-hexyne
y

32

ALKENES, ALKYNES & AROMATIC

COMPOUNDS

Aromatics are unsaturated ring molecules

They are often drawn to look like alkenes
alkenes, but they
behave much differently than alkenes.
They have an alternating pattern of double and
single bonds within a ring.
Benzene is an example

33

ALKENES, ALKYNES & AROMATIC

COMPOUNDS

34

ALKENES, ALKYNES & AROMATIC

COMPOUNDS

The physical properties of all hydrocarbons are

the same

The have essentially one noncovalent interaction,

which
hi h is
i the
h London
L d dispersion
di
i force.
f

They
y have no electronegative
g
atoms and therefore
have

no ion/ion interactions

no dipole/dipole interactions

no hydrogenbonding interactions
35

ALKENES, ALKYNES & AROMATIC

COMPOUNDS

Naming of Alkenes and Alkynes work the same

as for alkanes, with these added rules:

The parent chain must include both carbons in all

double and triple bonds.
bonds

Pick the longest chain that also contains all double and triple
bonds

The -ene ending is used of alkenes

The -yne ending is used for alkynes.

The number of the first carbon in the double or triple bond is

included in the name to locate the double or triple bond.
Number the parent chain from the end that is closes to the
fi
first
d
double
bl or triple
i l b
bond.
d

36

ALKENES, ALKYNES & AROMATIC

COMPOUNDS

Naming of Aromatics is based on benzene:

When the molecule is build on benzene
benzene, the parent
name is benzene.
There are also many common names used to describe
aromatic compounds.

37

ALKENES, ALKYNES & AROMATIC

COMPOUNDS

Naming of Aromatics is based on benzene:

Aromatic compounds can contain multiple aromatic

rings

38

ALKENES, ALKYNES & AROMATIC

COMPOUNDS

Benzo(a)pyrene found in tobacco smoke is

converted to carcinogenic products in the liver
which link to DNA and cause mutations.

39

ALKENES, ALKYNES & AROMATIC

COMPOUNDS

Benzo(a)
Benzo
(a)pyrene
pyrene

40

ALKENES, ALKYNES & AROMATIC

COMPOUNDS

Th
There
are many aromatic
ti molecules
l
l found
f
d in
i biology
bi l
Some aromatic compounds contain nitrogen and oxygen
atoms
For example, the nucleotide base Adenine, which is used to
make DNA and RNA

NH2
N

N
N

41

ALKENES, ALKYNES & AROMATIC

COMPOUNDS

Like cycloalkanes, some alkenes can have cis and

trans isomers

This is due to restricted rotation about the doublebond.

bond

Not all double bonds produce cis and trans isomers

42

ALKENES, ALKYNES & AROMATIC

COMPOUNDS

Each carbon participating in the double

bond must have two different
substituents attached to them
A

X
C

C
Y

A B AND X Y
43

ALKENES, ALKYNES & AROMATIC

COMPOUNDS

Like cycloalkanes, some alkenes can have cis and

trans isomers

44

ALCOHOLS, CARBOXYLIC ACIDS & ESTERS

In addition to the four families of hydrocarbons,

there are also many other families of organic
molecules.
These other families include elements other than
y
g
carbon and hydrogen.

They exhibit a wide range of chemical and physical

properties.

The families are distinguished by a group of atoms

called a functional group
45

ALCOHOLS, CARBOXYLIC ACIDS & ESTERS

Functional Group
A

functional group is an atom, group of

atoms or bond that gives a molecule a
particular set off chemical and p
p
physical
y
properties.

46

ALCOHOLS, CARBOXYLIC ACIDS & ESTERS

The carbon-carbon double bonds found in alkenes

is an example of a functional group.

A chemical p
property
p y of a double is that it will absorb
hydrogen in the hydrogenation reaction.

47

ALCOHOLS, CARBOXYLIC ACIDS & ESTERS

We look now at three families that are

distinguished by a functional group that contains
the element oxygen.
Al h l
Alcohols

Members of the alcohol family contain a hydroxyl

group.

48

ALCOHOLS, CARBOXYLIC ACIDS & ESTERS

Alcohols

The hydroxyl group comprises an oxygen with one

single bond to a hydrogen and another single bond to
an alkane-type carbon

An alkane
alkane--type carbon atom

ethanol

H hydroxyl group

49

ALCOHOLS, CARBOXYLIC ACIDS & ESTERS

We look now at three families that are

distinguished by a functional group that contains
the element oxygen.

50

ALCOHOLS, CARBOXYLIC ACIDS & ESTERS

Carboxylic acids
Members of the carboxylic acid family contain a
carboxylic acid group
The carboxylic acid group comprises a hydroxyl
group connected to a carbonyl group:

O
C
carbonyl group

hydroxyl group

carboxylic acid group

51

ALCOHOLS, CARBOXYLIC ACIDS & ESTERS

Carboxylic acids

The present of the hydroxyl group next to the cabonyl

group completely changes it properties.
The alcohol hydroxyl group and the carboxylic acid hydroxyl
group are chemically quite different, which is why molecules
that have the carboxylic acid group are placed in a separate
f il from
family
f
the
th alcohols.
l h l

52

ALCOHOLS, CARBOXYLIC ACIDS & ESTERS

Carboxylic acids

Later in the semester we will learn about some of these

chemical differences.

O
C
carbonyl group

hydroxyl group

carboxylic acid group

53

ALCOHOLS, CARBOXYLIC ACIDS & ESTERS

Carboxylic acids

The carboxylic acid group can be attached to a

hydrogen, an alkane-type carbon, or an aromatictype carbon:
O
H

OH

methanoic acid
((formic acid))

OH

propanoic acid

OH

benzoic acid

54

ALCOHOLS, CARBOXYLIC ACIDS & ESTERS

We look now at three families that are

distinguished by a functional group that contains
the element oxygen.

55

ALCOHOLS, CARBOXYLIC ACIDS & ESTERS

Esters

Chemically, esters can be synthesized by reacting a

Chemically
carboxylic acid with and alcohol:

O
C

O
O

carboxylic
acid

alcohol

ester

water

56

ALCOHOLS, CARBOXYLIC ACIDS & ESTERS

Esters

Chemically, esters can be synthesize by reacting a

Chemically
carboxylic acid with and alcohol:

O
CH3

CH2

Carboxylic
acid part

CH2 CH3
Alcohol
part
p

Ethyl propanoate

57

ALCOHOLS, CARBOXYLIC ACIDS & ESTERS

Carboxylic acids

The carboxylic acid group can be attached to a

hydrogen, an alkane-type carbon, or an aromatictype carbon:
O
H

OH

methanoic acid
((formic acid))

OH

propanoic acid

OH

benzoic acid

58

ALCOHOLS, CARBOXYLIC ACIDS & ESTERS

As we saw with the hydrocarbons, the physical

properties
p
p
of organic
g
molecules depend
p
on the
noncovalent intermolecular interactions which
attract one one molecule to another.

With hydrocarbons, there is only one type of

noncovalent interaction:
Induced dipole/Induced dipole (London dispersion force)

The presence of the electronegative oxygen makes

alcohols, carboxylic acids and esters polar molecules,
these families, therefore, have at least two types of
noncovalent
l
i
interactions:
i
Induced dipole/Induced dipole (London dispersion force)
Dipole/Dipole

59

ALCOHOLS, CARBOXYLIC ACIDS & ESTERS

As we saw with the hydrocarbons, the physical

properties of organic molecules depend on the
noncovalent intermolecular interactions which
attract one one molecule to another.

Alcohols and Carboxylic acids also have a hydroxyl

group with a hydrogen bonded to an oxygen
oxygen. This
allows them to form hydrogen bonds with each
y acids have at least three
other. Therefore,, carboxylic
different noncovalent interactions:
Induced dipole/Induced dipole (London dispersion force)
Dipole/Dipole
Hydrogen bond

60

ALCOHOLS, CARBOXYLIC ACIDS & ESTERS

To summarize, the types of noncovalent interact

ions that each family can participate in include:

Hydrocarbons (Alkanes, Alkenes, Alkynes &

A o atics)
Aromatics)
Induced dipole/Induced dipole (London dispersion force)

Esters
Induced dipole/Induced dipole (London dispersion force)
Di l /Di l
Dipole/Dipole

Alcohols & Carboxylic acids

Induced dipole/Induced dipole (London dispersion force)
Dipole/Dipole
Hydrogen bond

61

ALCOHOLS, CARBOXYLIC ACIDS & ESTERS

These interactions are illustrated in Figure 4.23

of your textbook.

alcohols

esters
62

carboxylic acids

ALCOHOLS, CARBOXYLIC ACIDS & ESTERS

Boiling points are a good measure of the strength

of the noncovalent interactions between
molecules.

The stronger the interactions

interactions, the higher the boiling
point will be.

Since all molecules have the London dispersion

interaction, the boiling points of molecules is
expected to increase with temperature.
temperature

The next slide shows a chart using the data found in

Table 4.7 of Raymond, in which the boiling points
for alcohols, carboxylic acids and esters are plotted
against molecular weight.
weight

63

As expected
expected, the boiling
points for members of all
three families increases
with molecular weight due
t the
to
th London
L d dispersion
di
i
interactions.

For a given molecular

weight,
i ht the
th alcohols
l h l and
d
carboxylic acids have a
higher boiling point than
esters, this is because they
can form hydrogen bonds
and esters cannot.

The carboxylic acids have

a slightly higher boiling
point than alcohols,
because they can form two
hydrogen bonds with a
neighboring molecule (See
Figure 4.23 in Raymond)

B
Boiling
Point {C}

ALCOHOLS, CARBOXYLIC ACIDS & ESTERS

64

Molecular Weight {g/mol}

ALCOHOLS, CARBOXYLIC ACIDS & ESTERS

Another distinguishing characteristic of many of the

families is odor.

You nose is actually a highly sensitive chemical

detector.

The members of different families can interact

differently with the receptors in your nose to produce
smells that are characteristic of the families they belong
to.

For example:

Carboxylic acids produce the pungent, sometime unpleasant odors

associated with ripe cheeses, rancid butter and vomit.
Esters, on the other hand,
Esters
hand produce the sweet,
sweet often pleasant order
associated with flowers, perfumes and various natural and
artificial flavorings. The next slide shows Figure 4.24 from
Raymond, which gives some specific examples.

65

ALCOHOLS, CARBOXYLIC ACIDS & ESTERS

Examples
of some
flavorable
esters:

66

THE END

67