Reactions of Functional Groups
Functional
Group
Reaction
Example
Alkane
Combustion
alkane + O2  CO2 + H2O
Alkene /
Alkyne
+ H2O  add H and OH alcohol
asymmetric
+ HX  add H and X
alkylal
halide
+ X2  add X and X
 alkyl halide
symmetrical
+ H2  add H and H
alkane/ene
alkene/yne
alkene/yne
X is
alkene/yne
halid
alkene/yne
e
Addition
** alkynes may undergo two additions in a row to
become an alkane
Symmetrical Alkene: identical groups on either side of double bond
CH2=CH2
Asymmetrical Alkene: different groups on either side of double bond
CH2=CHCH3
 MARKOVNIKOV’S RULE: “the rich get richer”
In an addition reaction, H or OH is added to the more substituted carbon atom
(C atom bonded to the largest number of C atoms)
symmetrical
+
asymmetrical

1 isomer
H3C
CH3CH=CHCH3
+

HOH
H2 C
Cl2
+
asymmetrical
CH2=CHCH3
+
CH
OH
H
CH
Cl

CH
CH3
CH3
Cl

2 isomers
(one is more observed due to
asymmetrical
Markovnikov’s Rule)
CH2=CHCH2CH3 +
Aromatic
Compound
s
will NOT
undergo
addition
Substitution
(replace H or
Functional
Group)
Substitution
(with halogen
acid)
HBr

H
Br
CH2
CH
Br
CH2 CH3
H
CH CH2
+
more observed
CH2
CH3
no addition
+
Br
FeBr3
+
Br Br
alcohol + halogen acid  alkyl halide + water
OH
+
HBr
Br
+
Alcohols
Elimination
(with strong
acid and
dehydration
agent)
HBr

alcohol
OH
alkene
H2SO4

+
water
+
H2O
H2O
alcohol + [O]  aldehyde, ketone, carboxylic acid
1° alcohol  aldehyde  carboxylic acid
2° alcohol  ketone
3° alcohol  no reaction
Oxidation
Alkyl
Halides
Substition
(with OH of
base)
alkyl halide + base  alcohol + halogen acid
Br
+
+
OH
-OH
aldehyde
+

[O]
Br
-
carboxylic acid
O
O
Oxidation
+
C
[O]
C
H
OH
Aldehydes
aldehyde
+

[H]
1° alcohol
O
OH
Reduction
+
C
[H]
C
H
H
ketone
Oxidation
+
ketone
Ketones
[O]

no reaction
[H]

2° alcohol
+
O
OH
Reduction
+
C
[H]
C
carboxylic acid + base  salt + water
O
Neutralizatio
n
O
+
C
+
NaOH
C
OH
H2O
ONa
carboxylic acid + alcohol  ester + water
O
Carboxylic
Acids
Condensatio
n or
Esterification
O
+ HO
C
CH3
+
C
OH
O
H2O
CH3
carboxylic acid + amine  amide + water
O
O
+H2N
C
CH3
+
C
OH
NH
H2O
CH3
carboxylic acid + [H]  aldehyde and alcohol
O
Reduction
+
C
O
C
H
 salt of carboxylic acid + alcohol
O
C
[H]
H
ester + base
Hydrolysis
+
C
OH
Esters
OH
O
[H]
CH3
+
NaOH
H2SO4
O

C
+
ONa
HO
CH3
amide + water
 carboxylic acid + amine
O
Amides
Hydrolysis
C
HN
CH3
+
NaOH
H2SO4
O

C
+
OH
H2N
CH3