key

Name: ___________________________________________________________ Period: _________

Lecture 48
Heteroatom Functional Groups
Student Notes

Learning Objective(s)
• Identify the heteroatom functional groups in organic molecules
• Write systematic IUPAC names for each of the heteroatom functional groups
• Draw the structure formula of an organic molecule from its IUPAC name

Functional Groups

of _________within
group ____
A functional group is a _________ atoms a
chemical
characteristic _____________
molecule that has a _____________________
behavior
______________. Functional groups make it possible to classify
families
compounds into ______________.

The presence of a functional group in a hydrocarbon alters the

properties of the compound significantly and the chemistry of
organic molecules, regardless of their size or complexity, is
determined by the functional groups it contains

Alcohols

Alcohols are organic compounds containing the -OH functional

hydroxyl __________.
group which is called the _______________ group Alcohols
have the generic formula R-OH.

When naming alcohols:

• The base chain is the longest continuous carbon chain that

contains the -OH functional group

• The base name has the ending -ol

• The base chain is numbered so that the -OH group has the
lowest possible number Note: Alcohols are lower priority than the
other functional groups we will look at
• The number location of the hydroxyl group is inserted just today. In those cases, the alcohol is a
before the suffix substituent. If an OH group is a
substituent, it is hydroxy-
One way of classifying alcohols is based on which carbon atom is bonded to
the hydroxyl group.

•If this carbon is primary (1°, bonded to only one other carbon atom), the
alcohol
primary __________.
compound is a __________
alcohol has the hydroxyl group on a secondary
secondary ____________
•A _____________
(2°) carbon atom, which is bonded to two other carbon atoms.

tertiary
•A _____________ alconol
____________ has the hydroxyl group on a tertiary (3°)
carbon atom, which is bonded to three other carbons.
 2
I
345
6
7 123
l
54

2
I 123 +
s
C

3 3 I
.
5 +
4 2

I
I 4
23 3 5
12345
2
4

U 5

# IUPAC Name AND Classify the Alcohol by Degree

1
Heptan -

4-01

2
3 -

methylcyclonex-3-en-1-01
3
4- bromonexan-1-ol

4
1 , 4-dimethyl pentan-1-0)
5
3. Chloro-3-ethylhexan-2-o

6
3 -
Chloro-2-methylcyclonex- 2-en-1-01
7
3 -

methylbutan-1-ol
8
. iodo-3 , 3-dimethyl
2 pentan-2-o
 Aldehydes

Aldehydes are organic compounds containing the C=O functional group

carbonyl__________.
which is called the _____________ group In aldehydes, the carbonyl
hydrogen on at least one end.
group is attached to a ______________

We can systematically name simple aldehydes according to the number of IUPAC Name: Methanal
carbon atoms in the longest continuous carbon chain that contains the Common Name: Formaldehyde
carbonyl group with the suffix -al.
Note: In aldehydes, you don’t need to add a
The most familiar aldehyde is probably formaldehyde (common name) number location of the carbonyl carbon
which is a gas with a pungent odor. It is often mixed with water to make because it has to be on an end (carbon 1) to
formalin which used as a preservative be an aldehyde.

4321
54 3
2

3 I
5 32 I
, 4 2

4 32
634321 5
4321

# IUPAC Name

1
2, 3- dimethyl butanal
2
2-chloropentanal
3
4 -

ethyl-6-hydroxy-3-methylhexanal
4 4 -

hydroxybutanal
5
3-methyl-2-propylpentanal (2-isobutyl
pentanal)
6
2-methylpentanal
7 4
.
hydroxy-3-methylbutanal
 Ketones

Ketones are organic compounds also containing the C=O functional group
which is called the _____________
carbonyl __________.
group In ketones, the carbonyl
group is attached to ____________
Carbons on both ends.

IUPAC Name: Propan-2-one

We can systematically name simple ketones according to the number of Common Name: Acetone
carbon atoms in the longest continuous carbon chain that contains the
carbonyl group with the suffix -one. Note: In ketones, you DO need to add a
number location of the carbonyl carbon
The most familiar ketone is probably acetone (common name) which is the because it is not on an end like with
main component in nail polish remover. aldehydes

4
1234 2
5 3 I

4 l
3
S
I 2

2 I
S

3
4

l 4
32
2

34
I 7 S

24
Y
S 7
5

# IUPAC Name

1
butan-2-one
2
cyclopentanone
3
,3
3 -diethyl -

4-methyl cyclopentanone
4
3- ethyl hexan-2-one

5
6-methylhept-5-en-3-one
6
5-bromopentan-2-one
7 . bromo-7-chloro-6-hydroxy- 2 ,
5 2 5-trimethyloct-7-en-4-one
,

8 7. bromooct-4-en-3-one
 Carboxylic Acids IUPAC Name: Ethanoic Acid
CooH Common Name: Acetic acid
Carboxylic acids are organic compounds also containing the ________
functional group.

We can systematically name simple carboxylic acids according to the IUPAC Name: 2-
number of carbon atoms in the longest continuous carbon chain that hydroxypropanoic acid
Suffix-oic
contains the COOH group with the ____________ acid
________________. Common Name: Lactic
acid
The most familiar carboxylic acid is probably acetic acid (common name)
which is the active ingredient in vinegar and lactic acid (common name) Note: In carboxylic acids, you don’t need to
which collects in muscles after intense exercise causing soreness. add a number location of the carbonyl
carbon because it has to be on an end
weak
Carboxylic acids are a class of ________ ______________ acids
organic __________. (carbon 1) to be a carboxylic acid

54321 65432 ,

3
5
5 2
43
3 4 2

4 I
5
2

5 l 5 43 2
5 T
I
3
2 I
4 2
4 6 8
3
I
(this is actually a
ketone)

# IUPAC Name

1 2 iodo-3-methyl pentanoic acid

2
4-methyl pentanoic acid
3
3, 4-dimethy/nex-3-enoic acid
4
Pentanoic acid

5
Oct-I-en-3-one

6
5-bromo-4-hydroxy nex-2-enoic acid
7
2-methylpentanoic acid
8
Pent-3-ynoic acid
 Esters
Fun Fact: Esters are best
from an
Esters are organic compounds often derived ____________ sweet
known for their __________
alcohol and Carboxylic
___________________ ________________acid________. Smells
___________. Methyl
butanoate is responsible for
Esters are named as if the alkyl chain from the alcohol is a substituent. Then the smell and taste of apples.
the parent name is the carboxylic acid part of the ester with the suffix -oate. Ethyl butanoate is responsible
for the smell and taste of
pineapples.

methanoate
ethy (

X
Sh nexanoate
4 ethyl

ethyl butanoate
cyclopentyl
2-methyl but
anoate
/L It
pentanoate
ethyl

# IUPAC Name

1
ethyl methanoate
2 butanoate
ethyl
3
ethyl 2-methylbutanoate
4
ethyl hexanoate

5
cyclopentyl pentanoate
 Ethers

Ethers are organic compounds with the general formula ROR and the
2 R groups could be identical or different.

hydrocarbon
R represents a _________________ substituent
____________________.

Ethers are names according to the following format: (R group 1)(R

group 2) ether with the R groups in alphabetical order.

If the R groups are the same, we use the prefix di-

butyl buty cycionexel cyclohexyl

ethyl cyclonexyl
ethy

nexyl

ethyl buty (

# IUPAC Name

1
dibutyl ether
2
cyclohexyl ethyl ether
3
butyl ethyl ether
4
dicyclohexyl ether
5
ethyl nexyl ether
 Amines

Amines are nitrogen-containing compounds that are

derived from ammonia with one or more of the hydrogen
atoms replaced by alkyl groups.

We systematically name amines according to the

hydrocarbon groups attached to the nitrogen and assign
the ending -amine.

Amines are most commonly known for their awful odors.

Triethylamine causes the smell of rotten fish.

bases
weak__________.
Amines commonly behave as ________

# IUPAC Name
methyl
methyl
1 methylpropylamine
butyl
propyl 2
methyl ethylmethylpropylamine
3
ethyl butyl dimethylamine
1234 4 2-bromo-1-methyl butylamine
propyl
methyl 2 bromo-1-methyl butyl

Other Functional Groups Provide the IUPAC names for the following organic
compounds:
The basic aromatic substituents are phenyl and benzyl

I
I
23 42

# IUPAC Name

1
2-benzylbutanoic acid

2
1-benzyl-1 methyl ethanol
Write the names for the chemicals shown below
methyl

4321
I
5 4
3
2
I 23456 I
2
methyl methy methyl
methyl methyl ethy/

6
2

methyl" 3
I 3
I
5
I
3
I
3
methyl 2 2 4 2
4 4

bromo
promo

S
321 I
321

methyl 3 4
4
methy / 2 ()methyl
ethanoate

butanoate propyl pentanoate

ethyl
memul

21/ethe
" 3 3
14
I s
4 2 & a
4

# IUPAC Name
A 3-methyl butan-2-o)

B 3 , 4-dimethylpentan-2-one

C 2 , 4, 4-trimethy/nexan-3-ol
D ethylamine
E 3, 4- dimethylhexan-2-o
F butana (
G pentan-3-one
H butanoic acid

I 2-methylpropanoic acid
J butylamine
K 3, 3-dibromo-2-methylpentanal
L
methyl ethanoate
M
ethyl butanoate
N
propyl pentanoate
O
ethylmethylamine
Draw the organic structures using line notation given the names below
3,3,4-trimethylpentane-2-ol
⑳ dimethylether 2,4,6-trichlorohexan-3-ol
hexano
OH OH

O Cl Cl

Cl

3-ethyl-4,4-dimethylpentan-2-one 2,3,4-trimethylpentanoic acid 2,2,3,3-tetrachloropropanal

O O CI

Il Il
" H

C
Cl
Cl

ehtylmethylpropylamine methylethanoate Ethylamine

0 H-
i I H

2,3-dimethylbutanal 2-benzylpropanoic acid propylbutanoate

O
O
Il
II

!
HO
H

#I