Download Classes and Nomenclature of Halogen Compounds

By
Dr. Mohamed El-Newehy
Chemistry Department, College of Science, King Saud University
http://fac.ksu.edu.sa/melnewehy
Organic Halogen Compounds
Classes and Nomenclature of Halogen Compounds
- Alkyl halides, R-X.
- Depending on the type of carbon to which the halogen is attached, Alkyl halides are
subdivided into; primary (1°), secondary (2°), or tertiary (3°).
Classes and Nomenclature of Halogen Compounds
-Vinylic halides; A halogen attached directly to a doubly bonded carbon.
- Allylic halides; The halogen attached to a carbon next to a doubly bonded carbon.
Classes and Nomenclature of Halogen Compounds
- Aryl halides,Ar-X; The halogen is directly attached to an aromatic ring.
- Benzylic halides, Ar-C-X; The halogen one carbon away from an aromatic ring.
Classes and Nomenclature of Halogen Compounds
F
C
H
C
l
3
C
o
m
m
o
n
n
a
m
e
: M
e
t
h
y
lc
h
l
o
r
i
d
e
I
U
P
A
C
n
a
m
e
: C
h
l
o
r
o
m
e
t
h
a
n
e
o
C
l
a
s
s
:
1
C
H
C
H
C
H
B
r
3
2
2
n
P
r
o
p
y
lb
r
o
m
i
d
e
1
B
r
o
m
o
p
r
o
p
a
n
e
o
1
C
H
C
H
C
H
3
3
I
s
o
p
r
o
p
y
lf
l
u
o
r
i
d
e
2
F
l
u
o
r
o
p
r
o
p
a
n
e
o
2
I
C H
H 3C
3
C H 3C C H
C l
3
Br
C om m on nam e:
IU P A C n a m e :
C la s s :
C y c lo h e x y l io d id e
Io d o c y c lo h e x a n e
2o
t-B u ty l b ro m id e
2 -B ro m o -2 -m e th y lp r o p a n e
3o
M e th y lc y c lo p e n ty l c h lo r id e
1 -C h lo ro -1 - m e th y lc y c lo p e n ta n e
3o
Physical Properties of Halogen Compounds
- Solubility
• All organic halides are insoluble in water and soluble in common organic solvents (benzene,
ether).
- Boiling points
• Within a series of halides, the boiling points increase with increasing molecular weights.
Therefore, the boiling points increase in the order F < Cl <Br < I.
• Within a homologous series, the boiling points also increase regularly with molecular weights.
• Within a series of isomers, the straight-chain compound has the highest boiling point, and
the most branched isomer the lowest boiling point.
Preparation of Halogen Compounds
 Chloro, Bromo, and Iodo Compounds
1) Direct halogenation of hydrocarbons.
a) Halogenation of alkanes: Alkyl halides
b) Halogenation of alkenes: Allyl halides
c) Halogenation of alkyl benzenes: Benzyl halides
d) Halogenation of aromatic ring: Aryl halides
Preparation of Halogen Compounds
2) Addition of HX to unsaturated hydrocarbons
a) Addition of HX to alkenes: Alkyl halides
b) Addition of HX to alkynes: Vinyl halides
3) Conversion of alcohols: Alkyl halides
Reactions of Halogen Compounds
A) Nucleophiic substitution, or SN, reactions.
Those in which the halogen is replaced by some other atom or group.
B) Elimination, or E, reactions.
Those that involve the loss of HX from the halide.
C) Formation of organometallic compounds.
Those that involve reaction with certain metals.
Reactions of Halogen Compounds
A) Nucleophiic substitution, or SN, reactions.
RX +
Reactions of Halogen Compounds
B) Elimination, or E, reactions.
Alkyl halides can lose H and X from adjacent carbons to form alkenes by an
elimination process.
Reactions of Halogen Compounds
Elimination versus Substitution
Elimination is favored over substitution when strongly basic solutions and high
temperatures are used.
Reactions of Halogen Compounds
C) Formation of organometallic compounds.
 Most organic chlorides, bromides, and iodides react with certain metals to give
organometallic compounds, molecules with carbon-metal bonds.
 Grignard reagents are obtained by the reaction of alkyl or aryl halides with
metallic magnesium in dry ether as the solvent.
 General reaction
Specific example
Reactions of Halogen Compounds
C) Formation of organometallic compounds.
 Grignard reagents react readily with any source of protons to give hydrocarbons.