Functional Groups

Rainbow education

Elements in Organic Compounds

In organic molecules,
carbon atoms bond
with four bonds.
mostly with H and
other C atoms.
sometimes to O, N,
S,
sometimes to
halogens F, Cl, and
Br.
2

Functional Groups
Functional groups are
a characteristic feature of organic molecules
that behave in a predictable, similar way.
composed of an atom or group of atoms.
groups that replace a hydrogen atom in the
corresponding alkane.
a way to classify families of organic
compounds.
3

Alkenes and Alkynes

Alkenes contain a
double bond between
adjacent carbon atoms.
(Double bond: 4 electrons)

Alkynes contain a triple

bond.
(Triple bond: 6 electrons)

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Publishing as Benjamin Cummings

Organic compounds with

Carbon-Oxygen bonds
1. Alcohols
An alcohol contains the
hydroxyl (-OH)
functional group.
(instead of an H in that
place)

Ethanol
Copyright 2005 by Pearson Education, Inc.
Publishing as Benjamin Cummings

OH vs -OH
-

OH- : hydroxide anion found in bases

(e.g NaOH)

-OH: hydroxyl group colvalently bound to

carbon atom in an organic compound
(e.g. ethanol CH3-CH2OH)

2. Ethers
In an ether, an oxygen
atom is bonded to two
carbon atoms.
COC .
has a common name that
gives the alkyl names of
the attached groups
followed by ether.
Copyright 2005 by Pearson Education, Inc.
Publishing as Benjamin Cummings

Diethyl ether

3. Aldehydes
An aldehyde contains a
carbonyl group (C=O),
which is a carbon atom
with a double bond to an
oxygen atom.

formaldehyde

acetaldehyde
8

4. Ketones
In a ketone, the carbon of
the carbonyl group is
attached to two other
carbon atoms.

Acetone

5. Carboxylic Acids and Esters

Carboxylic acids contain the
carboxyl group, which is a
carbonyl group attached to a
hydroxyl group.
O

COH

Acetic acid
10

5. Esters
An ester contains the carboxyl
group between carbon atoms.

Methyl acetate

11

Organic compounds with CarbonNitrogen bonds

1. Amines
In amines, the functional
group is a nitrogen atom.
H
H
C N H or C N C

Methyl amine

Dimethyl amine
12

2. Amides
In amides, the hydroxyl
group of a carboxylic acid is
replaced by a nitrogen
group (-NH2).

acetamide

13

Functional Groups

14

Learning Check
Classify each of the following as: alcohol, ether,
aldehyde, ketone, carboxylic acid, ester, amine or
amide.
1) CH3CH2CH2OH
2) CH3OCH2CH3
3) CH3CH2NH2
O

4) CH3COH
carboxylic acid

alcohol
ether

amine

5) CH3COCH3
ester
15

Unsaturated Hydrocarbons
Cis-Trans Isomers
Chapter 11.2

16

Cis and Trans Isomers

In an alkene the double bond,
is rigid.
holds attached groups in fixed positions.
makes cis/trans isomers possible.
CH3
CH = CH
cis

CH3

CH3
CH = CH
trans

CH3
17

Cis-Trans Isomers
In cis-trans isomers
there is no rotation around
the double bond in alkenes.
groups attached to the
double bond are fixed
relative to each other.
You can make a double
bond with your fingers with
both thumbs on the same
side or opposite from each
other.
18

Cis-Trans Isomers
Two isomers are possible when
groups are attached to the
double bond are different.
(a double bond cannot rotate)
In a cis isomer, groups are
attached on the same side of
the double bond.
In the trans isomer, the
groups are attached on
opposite sides.
19

Cis-Trans Isomerism
Alkenes cannot have cis-trans isomers if a carbon atom
in the double bond is attached to identical groups.
Identical

Identical

Br
H
Br

HH

C C
CH3
HH
2-bromopropene
(not cis or trans)

Br

H
C C
H

Br

1,1 dibromoethene
(not cis or trans)
20

Cis-Trans Isomers in Nature

21

Organic Compounds with

Oxygen and Sulfur
12.1
Alcohols, Ethers, and Thiols

22

Alcohols
An alcohol contains a hydroxyl group (OH) attached to a
carbon chain.
A phenol contains a hydroxyl group (OH) attached to a
benzene ring.

water

alcohol

phenol
23

Naming Alcohols
The names of alcohols
in IUPAC replace the -e with -ol.
with common names use the name of the alkyl group
followed by alcohol.
Formula IUPAC
CH4

Common Name

methane

CH3OH methanol

methyl alcohol

CH3CH3 ethane
CH3CH2OH

ethanol

ethyl alcohol
24

Classification of Alcohols
Classification of alcohols is
determined by the number of alkyl groups attached to
the carbon bonded to the hydroxyl.
primary (1), secondary (2), or tertiary(3).
Primary (1)
1 group
H
|
CH3COH
|
H

Secondary (2)
Tertiary (3)
2 groups
3 groups
CH3
CH3
|
|
CH3COH
CH3COH
|
|
H
CH3
25

Thiols
Thiols
are carbon compounds that
contain a SH group.
are named in the IUPAC
system by adding thiol to
the alkane name of the
longest carbon chain.

not for 10 std.

26

Thiols
Thiols
often have
strong odors.
are used to
detect gas leaks.
are found in
onions, oysters,
and garlic.

27

Properties of Alcohols, Ethers,

and Thiols

28

Boiling Points of Alcohols

Alcohols
contain polar OH
groups.
form hydrogen bonds
with other alcohol
molecules.
have higher boiling
points than alkanes and
ethers of similar mass.

29

Boiling Points of Ethers

Ethers
do not have a polar
group.
have an O atom,
but there is no H
attached.
cannot form
hydrogen bonds
between ether
molecules.
30

Solubility of Alcohols and Ethers

in Water
Alcohols and ethers
are more soluble in water than alkanes because the
oxygen atom can hydrogen bond with water.
with 1-4 C atoms are soluble, but not with 5 or more
C atoms.

31

Comparing Solubility and

Boiling Points
Molar

Boiling

Compound
Mass
Alkane CH3CH2CH3 44

Soluble
Point (C) in Water?
-42
No

Ether

46

-23

Yes

46

78

Yes

CH3OCH3

Alcohol CH3CH2OH

32

Solubility of Phenol
Phenol
is soluble in water.
has a hydroxyl group that ionizes slightly (weak acid).
is corrosive and irritating to skin.
OH

O-

+ H2 O

+ H 3 O+

33

Combustion of Alcohols
Alcohols undergo combustion with O2 to produce
CO2 and H2O.
2CH3OH + 3O2

2CO2 + 4H2O + Heat

Copyright 2005 by
Pearson Education, Inc.
Publishing as Benjamin
Cummings

34

Oxidation and Reduction

In an oxidation,
there is an increase in the number of C-O bonds.
there is a loss of H.

In a reduction,
there is an decrease in the number of C-O bonds.
there is a gain of H.

35

Oxidation and Reduction

36

Oxidation of Primary (1)

Alcohols
When a primary alcohol is oxidized, [O],
one H is removed from the OH.
another H is removed from the carbon bonded to the OH.
an aldehyde is produced.
[O]
Primary alcohol
Aldehyde
OH
O
|
[O]
||
CH3CH
CH3CH + H2O
|
H
Ethanol
Ethanal
(ethyl alcohol)
(acetaldehyde)
37

Oxidation of Secondary (2)

Alcohols
When a secondary alcohol is oxidized, [O],
one H is removed from the OH.
another H is removed from the carbon bonded to the OH.
a ketone is produced.
[O]
secondary alcohol
ketone
OH
O

[O]

CH3CCH3
CH3CCH3 + H2O

H
isopropyl alcohol

dimethyl ketone

38

Oxidation of Tertiary Alcohols

Tertiary 3alcohols do not readily oxidize.
[O]
Tertiary alcohol
no reaction
OH

[O]
CH3CCH3
no product

CH3
no H on the C-OH to oxidize
2-methyl-2-propanol

39