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Alkyl Halides and Ethers

Alkyl halides, or haloalkanes, are compounds with a halogen atom bonded to a carbon atom, used as solvents, refrigerants, and in organic synthesis. They exhibit unique physical properties such as higher boiling points and densities compared to hydrocarbons due to dipole interactions. Ethers, containing an oxygen atom bonded to two R groups, are named based on the longest carbon chain and are less soluble in water than alcohols.

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12 views29 pages

Alkyl Halides and Ethers

Alkyl halides, or haloalkanes, are compounds with a halogen atom bonded to a carbon atom, used as solvents, refrigerants, and in organic synthesis. They exhibit unique physical properties such as higher boiling points and densities compared to hydrocarbons due to dipole interactions. Ethers, containing an oxygen atom bonded to two R groups, are named based on the longest carbon chain and are less soluble in water than alcohols.

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Alkyl Halides (Haloalkanes)

• Compounds containing a halogen atom covalently bonded to a


carbon atom are named haloalkanes, or, in the common system of
nomenclature, alkyl halides.
USES
• Several haloalkanes are important laboratory and industrial
solvents eg chloroform, dichloromethane.
• Invaluable building blocks for organic synthesis because of the
variety of ways in which the halogen may be substituted with other
groups or eliminated to produce p bonds.
Alkyl Halides (Haloalkanes)
USES
• Dichloromethane, chloroform and trichloroethene are used as
solvents, degreasing agents and for removal of organic stains from
glassware.
• However, their side effect is that they dissolve fats from the skin and
can accumulate in fat tissue. Therefore, they are suspected of
causing dermatitis.
• Inhaled anesthetics in medicine e.g. chloroform (CHCl3), CF3CHClBr
(1-bromo-1-chloro-2,2,2-trifloroethane).
Alkyl Halides (Haloalkanes)
USES
• Used as refrigerants—CF2Cl2 (CFC).
• The insecticide/Pesticides, DDT (Dichlorodiphenyltrichloroethane) is
used to control infectious insects such as mosquitoes. The problem
with DDT is that it is not easily biodegradable.
• 2,4-D ( 2,4-Dichlorophenoxyacetic acid) is used as a herbicide for
controlling weeds.
• Halogenated solvents such as trichloroethylene are used for
cleaning semiconductor chips and other components.
Alkyl Halides
Structure
• The general symbol for a haloalkane is R-X, where -X may be -F, -Cl,
-Br, or -I.
• If a halogen is bonded to a doubly bonded carbon of an alkene, the
compound belongs to a class called haloalkenes.
• If it is bonded to a benzene ring, the compound belongs to a class
called haloarenes, which have the general symbol Ar-X.
Structure
• Each carbon atom is described in terms of its proximity to the
halogen.
• The alpha ( ) position is the carbon atom connected directly to
the halogen, while the beta ( ) positions are the carbon atoms
connected to the alpha position.
Structure
• Alkyl halides are classified as primary (1°), secondary (2°), or
tertiary (3°) based on the number of alkyl groups connected to the
α position.
Nomenclature
• Recall that systematic (IUPAC) names of alkanes are assigned using
four discrete steps:
1. Identify and name the parent.
2. Identify and name the substituents.
3. Number the parent chain and assign a locant to each substituent.
4. Assemble the substituents alphabetically
• The same exact four-step procedure is used to name compounds
that contain halogens.
• Halogens are treated as substituents and receive the following
names: fluoro-, chloro-, bromo-, and iodo-.
Nomenclature

The parent is the longest chain, and it should be numbered so that


the first substituent receives the lower number.
Nomenclature

NOTE: Alkyl substituents and halogen substituents have similar


priorities.
Nomenclature
Q. Write the IUPAC name of each compound.
Physical Properties of Haloalkanes

Polarity
• Fluorine, chlorine, and bromine are all more electronegative than
carbon; as a result, C-X bonds with these atoms are polarized with
a partial negative charge on halogen and a partial positive charge
on carbon.
• The magnitude of a dipole moment depends on the size of the
partial charges, the distance between them, and the polarizability
of the three pairs of unshared electrons on each halogen.
Physical Properties of Haloalkanes
Dipole moments of Halomethanes
Halomethane Electronegativity Carbon-Halogen Dipole moments
of Halogen bond length (pm) (Debyes, D)

CH3F 4.0 139 1.85


CH3Cl 3.0 178 1.87
CH3Br 2.8 193 1.81
CH3I 2.5 214 1.62
Physical Properties of Haloalkanes
Boiling Point
Haloalkanes are associated in the liquid state by a combination of
attractive dipole-dipole, dipole-induced dipole, and induced dipole-
induced dipole (dispersion) forces.
• As with hydrocarbons, constitutional isomers with branched
chains have lower boiling points than their unbranched-chain
isomers.

1-bromobutane 2-bromo-2-methylpropane
b.p 100oC b.p 72oC
Physical Properties of Haloalkanes

• For an alkane and haloalkane of comparable size and shape, the


haloalkane has a higher boiling point. This is because of the dipole
moment in haloalkane and greater polarizability of the bromine
atom.

CH3CH3 CH3CH2Br
Ethane Bromoethane
b.p -89oC b.p 4oC
Physical Properties of Haloalkanes
Density
• The densities of liquid haloalkanes are greater than those of
hydrocarbons of comparable molecular weight because of the
halogens’ large mass-to-volume ratio.
• The densities of all liquid bromoalkanes and iodoalkanes are
greater than that of water.
• Although the densities of liquid chloroalkanes are less than that of
water, further substitution of chlorine for hydrogen increases the
density to the point where di- and polychloroalkanes have a
greater density compared to that of water.
Ethers
• Ethers are compounds that contain an oxygen atom bonded to two R
groups, where each R group can be an alkyl, aryl, or vinyl group.
Nomenclature of Ethers
• In the IUPAC system, ethers are named by selecting the longest
carbon chain as the parent alkane and naming the -OR group
bonded to it as an alkoxy group.
Nomenclature of Ethers
• A common name is constructed by identifying each R group,
arranging them in alphabetical order, and then adding the word
“ether”.

These are examples of unsymmetrical ethers.


Nomenclature of Ethers
• When the two alkyl groups are identical, the compound is called a
symmetrical ether and is named as a dialkyl ether.

Example
Nomenclature of Ethers
• NOTE: When one of the R groups is complex, the systematic name
is used.
• NOTE: Ethers have the same priority as halogens, alkyl substituents
and aryl groups.

Example: provide IUPAC name for the following compound.


Nomenclature of Ethers
Q. Provide an IUPAC name for each of the following compounds.
Nomenclature of Ethers
Crown Ethers
These are cyclic polyethers also called crown ethers because their
molecular models resemble crowns.
Nomenclature of Ethers
• Metal cations can be solvated by crown ethers.
Structure and Properties of Ethers
• The geometry of an oxygen atom is similar for water, alcohols, and
ethers.
• In all three cases, the oxygen atom is sp3 hybridized, and the
orbitals are arranged in a nearly tetrahedral shape.
Structure and Properties of Ethers
• Compare the boiling points of the following compounds:

• Both dimethyl ether and propane lack the ability to form hydrogen
bonds.

• Ethers therefore exhibit dipole-dipole interactions, which slightly


elevate the boiling point relative to propane.
Structure and Properties of Ethers
• Ethers are soluble in water, but less soluble than alcohols. Whereas
they can act as hydrogen bond acceptors, they CANNOT function
as hydrogen donors.
Structure and Properties of Ethers
Q. Arrange these compounds in order of increasing solubility in
water.

Q. Arrange these compounds in order of increasing boiling point.


Structure and Properties of Ethers
• Ethers with larger alkyl groups have higher boiling points due to
London dispersion forces between the alkyl groups on different
molecules.

• Ethers are often used as solvents for organic reactions.

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