Functional Groups

Functional Groups

Functional groups: special groups of

atoms attached to a hydrocarbon skeleton;
the most common sites of chemical
reactivity.
Organic halides: a hydrogen is replaced
by a halogen

fluoro-, chloro-, bromo-, iodo-

2-iodobutane
Organic halides: a hydrogen is replaced
by a halogen

fluoro-, chloro-, bromo-, iodo-

2,4-dibromo-1-hexene
Organic halides: a hydrogen is replaced
by a halogen

fluoro-, chloro-, bromo-, iodo-

1-bromo-2-chlorobenzene
Alcohols & phenols: contain the hydroxyl
group (-OH)

alcohols: at least 1 H on a hydrocarbon is replaced by OH

phenols: at least 1 H on an aromatic ring is replaced by OH

2-propanol
Alcohols & phenols: contain the hydroxyl
group (-OH)

alcohols: at least 1 H on a hydrocarbon is replaced by OH

phenols: at least 1 H on an aromatic ring is replaced by OH

3-methyl-1-butanol
Alcohols & phenols: contain the hydroxyl
group (-OH)

alcohols: at least 1 H on a hydrocarbon is replaced by OH

phenols: at least 1 H on an aromatic ring is replaced by OH

1,2-butanediol
ethers: compounds in which an O atom is
bonded to 2 organic groups: -C-O-C-

methoxymethane (dimethyl ether)

ethers: compounds in which an O atom is
bonded to 2 organic groups: -C-O-C-

methoxypropane (methyl propyl ether)

ethers: compounds in which an O atom is
bonded to 2 organic groups: -C-O-C-

methoxybenzene (methyl phenyl ether)

Carboxylic acids: compounds that contain the
carboxyl group

(general formula is R-COOH)

butanoic acid
Carboxylic acids: compounds that contain the
carboxyl group

(general formula is R-COOH)

ethanoic acid
Carboxylic acids: compounds that contain the
carboxyl group

(general formula is R-COOH)

3-methylpentanoic acid
Carboxylic acids: compounds that contain the
carboxyl group

(general formula is R-COOH)

benzoic acid
amines: derivatives of ammonia (NH3
)
in
wh
i
c
h1
or
more H a t
om sa rere place
dby organi
c
gr
ou
p
s
(a
l
ky
l
orary
lg roup s)

ammonia
amines: derivatives of ammonia (NH3
)
in
wh
i
c
h1
or
more H a t
om sa rere place
dby organi
c
gr
ou
p
s
(a
l
ky
l
orary
lg roup s)

methylamine
amines: derivatives of ammonia (NH3
)
in
wh
i
c
h1
or
more H a t
om sa rere place
dby organi
c
gr
ou
p
s
(a
l
ky
l
orary
lg roup s)

trimethylamine
amines: derivatives of ammonia (NH3
)
in
wh
i
c
h1
or
more H a t
om sa rere place
dby organi
c
gr
ou
p
s
(a
l
ky
l
orary
lg roup s)

2-aminobutane
amines: derivatives of ammonia (NH3
)
in
wh
i
c
h1
or
more H a t
om sa rere place
dby organi
c
gr
ou
p
s
(a
l
ky
l
orary
lg roup s)

1-amino-3-propylcyclohexane
*aniline: the simplest aromatic amine

aniline
*aniline: the simplest aromatic amine

3,5-dichloroaniline

Naming it “aniline”
make this carbon #1 by
definition
*aniline: the simplest aromatic amine

N,N-dimethylaniline
Summary of IUPAC rules for
naming organic compounds
 IUPAC: International Union of Pure and Applied
Chemistry
 International, non-governmental organization that is best
known for its system of nomenclature, which is now
recognized as the world authority in this field.
Rule #1: Identify the longest
chain of carbon atoms
a) The longest chain of carbon atoms gives the stem/root
of the name as shown in the table below:

# of C-atoms Stem in Example

in longest IUPAC name (C2
H2n
+2 fo
r
a
l
ka
n
es
)
chain
1 meth- CH4
,
me
th
a
n
e
2 eth- C2
H
,
6e
t
han
e
3 prop- C3
H
,
8p
r
opa
n
e
4 but- C4
H
1
0,
bu
t
an
e
5 pent- C5
H
1
2,
pe
nt
a
n
e
6 hex- C6
H
1
4,
he
xa
n
e
7 hept- C7
H
1
6,
he
pt
a
n
e
8 oct- C8
H
1
8,
oc
t
an
e
9 non- C9
H
2
0,
no
na
n
e
Rule #1: Identify the longest
chain of carbon atoms
b) If two chains have equal lengths, pick the one
with more branch points.
Rule #2: Number the carbons in
the main chain
Number chain to minimize the position/number of the
following in order of priority:
a) thing you’re naming the compound after (double bond if alkene;
-OH group if alcohol, etc)
a) note: for multiple double bonds -diene ,-triene ,-tetraene
b) first branch/substituent group
c) If both ends have the same first branching number, then
number chain to minimize position of second branch (and then
third and so on).
d) if still in need of a tie breaker, minimize # of substituent group
that comes first alphabetically

Note: in cyclic and aromatic (benzene derivatives) compounds,

no number needed if only one substituent.
Rule #3: Identify the functional group and
attach appropriate suffix
 Note: the name for the stem/root is derived from
the longest carbon chain, which may include the
carbon of the functional group.

Indicating position of the functional group: shown by a

number inserted before the functional group ending. The
number refers to the carbon atom to which the functional
group is attached when the chain is numbered starting at
the end that will give the smallest number to the group.
Class of compound Functional group Suffix in IUPAC
name
alkane   -ane

alkene   -ene
 
alkyne   -yne
 
alcohol   -anol
 
aldehyde   -anal
 
ketone   -anone
 
carboxylic acid   -anoic acid
 
amine   -anamine
   
Rule #4: Identify the side chains or substituent groups
Assign number of carbon at point of attachment.

Side chain/ substituent Prefix in IUPAC name Example

group
-CH3 methyl- 2-methylpropane

-C2
H
5 ethyl 3-ethylpentane

-C3
H
7 propyl- 4-propylheptane

-F, -Cl, -Br, -I fluoro-, chloro-, bromo-, iodo- tetrachloromethane

-NH2 amino- 2-aminoethanioic acid

 Rule #5: Assemble name as a single word
 #, substituent, root, suffix
a) List substituents alphabetically (i.e.butyl- before methyl- )

b) If multiples of one substituent are present: “di-,” “tri-,” “tetra,”

etc.
 Note: “di-,” “tri-,” “tetra,” etc. aren’t part of alphabetical
name triethyl-
( beforedimethyl- )

c) punctuation: commas between numbers; hyphens between

numbers and letters; merged into one word (exception:
acid = word #2 for carboxylic acids)