Functional Groups in Organic Chemistry

Summary Sheet - Functional Groups (1)
"Master Organic Chemistry"

masterorganicchemistry.com
August 2012 Version 1.1
Note - this sheet is not meant to be comprehensive. Your course
may provide additional material, or may not cover some of the
reactions shown here. Your course instructor is the final authority.
Omissions, Mistakes, Suggestions?
james@masterorganicchemistry.com
This sheet copyright 2012, James A. Ashenhurst
http://masterorganicchemistry.com
What Are Functional Groups?
Functional groups are collections of atoms that have a common pattern of chemical
reactivity
Alkane
R
C
O
H
C C
H
H H
H3C
H
3
C
H2
C
CH
3
a hydrocarbon with no multiple bonds is an alkane
Characteristics: nonpolar
Geometry: tetrahedral (sp
3
hybridized)
Reactivity: free radical reactions (e.g. free radical chlorination or bromination)
Alkene
a hydrocarbon with at least one CC double
bond (! bond) is an alkene
Characteristics: nonpolar. Molecule cannot rotate along double bond.
Geometry: trigonal planar (sp
2
hybridized)
Reactivity: undergo addition reactions, as well as oxidative cleavage
Stability increases with increasing # of carbons attached
C C H H
3
C
Alkyne
a hydrocarbon with at least one CC
triple bond (! bond) is an alkyne
Alkynes with a CH bond are called "terminal" alkynes
Characteristics: non polar
Reactivity: addition reactions
oxidative cleavage reactions
acid-base reactions (terminal alkynes are unusually acidic)
Propyne
a terminal alkyne
2-butyne 3-heptyne
Propane Butane
( )
8
Decane 2-methylpentane
Propene trans-2-butene
[or (E)-2-butene]
cis-2-butene
[or (Z)-2-butene]
(E)-3,5-dimethylhex-2-ene
Benzene ring
A six-membered ring containing
3 alternating double bonds is a
benzene ring
Benzene Methylbenzene
(toluene)
1,4-dimethylbenzene
(para-dimethylbenzene)
Geometry: linear (sp hybridized)
Examples:
Examples:
Examples:
Examples:
Alcohol
OH
H
3
C
OH
The OH group is an alcohol [unless OH is attached to C=O,
in which case it's a carboxylic acid (below)]
Characteristics: polar (O-H group participates in hydrogen bonding)
Methanol Ethanol
a primary alcohol
2-propanol ("Isopropanol")
a secondary alcohol
Examples: OH
OH
2-methyl-2-propanol
(t-butanol)
a tertiary alcohol
R O H
" "
+
Reactivity: acid-base reactions (can act as acids or bases)
substitution reactions (can act as nucleophiles)
oxidation reactions (primary and secondary alcohols (and methanol)
can be oxidized to aldehydes, ketones, or carboxylic acids, depending
on structure and reagent used)
Ether
O
H
3
C
O
An oxygen flanked by two carbons is an ether
Characteristics: borderline between nonpolar and polar (due to dipole-dipole)
Dimethyl ether
Examples:
R O R
" "
+
Reactivity: acid-base reactions (oxygen can act as a very weak base
CH
3
Ethyl methyl ether
(or "methoxyethane")
Methyl phenyl ether
(or "methoxybenzene",
or "anisole")
O
Alkyl halide F R Cl R Br R I R
"
+
"
+
"
+
"
+ "
"
"
"
An alkyl group attached to

a halogen is an alkyl halide
Characteristics: generally considered non polar (but more polar than alkanes)
Reactivity: substitution reactions (Cl, Br, I can be good leaving groups)
elimination reactions (Cl, Br, I can be good leaving groups)
F
H
3
C
I
Iodomethane
(methyl iodide)
Fluoroethane
(ethyl fluoride)
a primary alkyl
halide
2-chloropropane
(isopropyl chloride)
a secondary alkyl halide
Examples:
Cl
Br
2-methyl-2-bromopropane
(t-butyl bromide)
a tertiary alkyl halide
Reactivity: substitution reactions (e.g. electrophilic aromatic substitution
or nucleophilic aromatic substitution)
C C
C
C C
O
Tetrahydrofuran (THF)
a cyclic ether
Suffix: "-ane". As a substituent: "alkyl"
Suffix: "-ene". As a substituent: "alkenyl"
Suffix: "-yne". As a substituent: "alkynyl"
Suffix: "benzene". As a substituent: "phenyl"
Suffix: "-ol". As a substituent: "hydroxy"
As a substituent: "alkoxy"
Suffix: "-ane". As a substituent: "haloalkyl"
Amine
NH2 H
3
C
NH
2
A nitrogen attached to simple carbon or
hydrogen atoms is an amine
Methylamine Ethylamine
a primary amine
Dimethylamine
a secondary amine
Examples:
H
N
Triethylamine
a tertiary amine
R N H
" "
+
H
Suffix: "-ine". As a substituent: "amino"
N
Characteristics: polar (N-H group participates in hydrogen bonding, although not as
much as a hydroxy group
Reactivity: acid-base reactions (tend to act as bases)
substitution reactions (can act as nucleophiles)
Aldehyde
A carbonyl (C=O) attached to a hydrogen
and another carbon is an aldehyde
Ethanal Propanal Butanal
Examples:
Benzaldehyde
"
#
"
+
Suffix: "-al" (if attached to ring: carbaldehyde) As a substituent: "oxo"
Characteristics: the C=O bond is somewhat polar
Reactivity: addition reactions (the carbonyl carbon reacts easily with nucleophiles)
H
3
C
C
O
H
O
H
O
H
O
H
R
C
O
R
Ketone
A carbonyl (C=O) flanked by two carbons
is a ketone
Examples:
"
#
"
+
Suffix: "-one". As a substituent: "oxo"
2-propanone
("acetone")
H
3
C
C
O
CH
3
2-butanone
("methyl ethyl ketone")
O
Characteristics: the C=O bond is somewhat polar (less so than O-H however)
Reactivity: addition reactions (the carbonyl carbon reacts easily with nucleophiles)
O
phenyl methyl ketone
("acetophenone")
3-hexanone
O
acid-base reactions (carbons adjacent to the ketone can be deprotonated
to give enolates)
R
C
O
O
Carboxylic acid
A carbonyl (C=O) adjacent to a hydroxyl
(OH) and an R group is a carboxylic acid
"
#
"
+
Suffix: "-oic acid"
H
"
#
"
+
Examples:
Methanoic acid
("formic acid")
H
C
O
OH
Ethanoic acid
("acetic acid")
O
OH
O
OH
benzoic acid Butanoic acid
O
R
C
O
O
Ester
A carbonyl (C=O) adjacent to an alkoxy
(OR) and an R group is an ester
"
#
"
+
Suffix: "-oate"
Examples:
Methyl methanoate
H
C
O
OCH3
Methyl ethanoate
O
O
O
O
Methyl benzoate Ethyl butanoate
O
O
R
Reactivity: acid-base reactions (the OH is acidic)
acyl substitution reactions (can replace OH with other groups under
acidic conditions)
Reactivity: acyl substitution reactions (can replace OR with other functional
groups under acidic conditions)
addition reactions (the carbonyl carbon reacts easily with nucleophiles)
Less reactive than normal alkenes due to aromatic stability

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Summary Sheet - Functional Groups (1)

"Master Organic Chemistry"

An alkyl group attached to

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