ALKYL HALIDES

TERMINOLOGIES
Aliphatic hydrocarbon - an organic compound containing hydrogen and carbon
atoms that are usually linked together in chains via single, double or triple
bonds.
Electrophilic - a chemical species that forms bonds with nucleophiles by
accepting an electron pair.
Nucleophilic - substances that tend to donate electron pairs to electrophiles in
order to form chemical bonds with them.
Polar bond - a covalent bond between two atoms where the electrons forming
the bond are unequally distributed.
Volatile - substances have a tendency to vaporize.
Alkyl halides, also called haloalkanes or halogenoalkanes, are chemical
compounds that are often derived from alkanes that contain one or more
halogens.

They are formed by the replacement of hydrogen atoms in an aliphatic

hydrocarbon by halogen atoms.
Halogen is any of the six nonmetallic elements that constitute Group 17
(Group VIIA) of the periodic table. The halogen elements are fluorine (F),
chlorine (Cl), bromine (Br), iodine (I), astatine (At), and tennessine (Ts).

They were given the name halogen, from the Greek roots hal- “salt” and -
gen “to produce” because they all produce sodium salts of similar properties,
of which sodium chloride—table salt or halite—is best known.
 PROPERTIES
• Alkyl halides are colourless when they exist in pure form. But,
bromides and iodides develop colour when exposed to light.
• They are soluble in most organic solvents.
• They have higher boiling points when compared to the
corresponding alkanes.
• Methyl chloride, methyl fluoride, ethyl fluoride, and ethyl chloride
are gases, but the rest of the lower members of the series are
liquids.
 PROPERTIES

• In their pure state, alkyl halides have a pleasant odour. However, all
the higher alkyl halides don’t have any odour.
• Alkyl bromides and alkyl iodides are generally heavier than water.
However, alkyl chlorides are lighter than water.
• Many volatile halogen compounds have a sweet smell.
 NOMENCLATURE
The common names of alkyl halides consist of two parts:
1. Common Name: the name of the alkyl group plus the name of the halogen, replacing the suffix -ine
with -ide.
2. IUPAC Name: the location of the halogen/alkyl group, the prefixes of the halogen substituents
(fluoro-, chloro-, bromo-, and iodo-) and the alkyl group, plus the alkane name.

Note that in naming alkyl halides, the halogen substituent is more prioritized than the alkyl group. The
arrangement of naming is also in alphabetical order.

Alkyl halides with simple alkyl groups (1-4 carbon atoms) are often called by common names. Those
with a larger number of carbon atoms are usually given IUPAC names.
 NOMENCLATURE

EXAMPLES
 CLASSIFICATIONS
Alkyl halides fall into different classes depending on how the halogen atom is positioned on the
chain of carbon atoms. They can be classified as primary, secondary, or tertiary. The chemical
reactivity of alkyl halides is frequently discussed using alkyl halide classifications to help
discern patterns and trends. Alkyl halide classification is determined by the bonding pattern of
the carbon atom bonded to the halogen as shown in the diagram below.
 CLASSIFICATIONS
1. Primary Alkyl Halides
In a primary (1°) haloalkane, the carbon bonded to the halogen atom is only attached to one
other alkyl group. Some examples of primary alkyl halides include the compounds below.

Notice that it doesn't matter how complicated the attached alkyl group is. In each case there is only
one linkage to an alkyl group from the CH2 group holding the halogen. There is an exception to
this: CH3Br and the other methyl halides are often counted as primary alkyl halides even though
there are no alkyl groups attached to the carbon with the halogen on it.
 CLASSIFICATIONS
2. Secondary Alkyl Halides
In a secondary (2°) haloalkane, the carbon bonded with the halogen atom is joined
directly to two other alkyl groups that can be the same or different. Some
examples of secondary alkyl halides include the compounds below.
 CLASSIFICATIONS
3. Tertiary Alkyl Halides
In a tertiary (3°) halogenoalkane, the carbon atom holding the halogen is attached
directly to three alkyl groups, which may be any combination of same or
different. Some examples of tertiary alkyl halides include the compounds below.
 REACTIONS

Alkyl halides can undergo two major types of reactions and these are:

1. Substitution Reaction/Nucleophilic Substitution Reaction

2. Elimination Reaction
 NUCLEOPHILIC SUBSTITUTION REACTION
The substitution reaction is also called a Nucleophilic Substitution Reaction
because the electrophilic alkyl halide forms a new bond with the
nucleophile which substitutes for (replaces) the halogen at the alpha-
carbon. Because carbon can only form four bonds, the halogen must leave
and is called the "leaving group". Alkyl halides are excellent electrophiles
because halogens share a polar bond with carbon, are polarizable, and form
relatively stable leaving groups as halide anions.
NUCLEOPHILIC SUBSTITUTION REACTION
 ELIMINATION REACTION

Allkyl halides can also undergo elimination reactions in the presence of strong
bases. The elimination of a beta-hydrogen (hydrogen on a carbon vicinal to the
alkyl halide carbon) and the halide produces a carbon-carbon double bond to
form an alkene.
ELIMINATION REACTION
 ELIMINATION REACTION
In the example below, 2-bromopropane has undergone an elimination
reaction to give an alkene - propene.
 REACTIONS

In all cases, you will get a mixture of both reactions happening—some

substitution and some elimination. The product distribution depends on
a number of factors. Depending on the structure of the alkyl halide,
reagent type, reaction conditions, some reactions will only undergo
only one pathway—substitution or elimination.
 USES
• Many organic compounds containing halogens occur in nature,
and some of them are clinically useful.
• These classes of compounds find good applications in industry as
well as in day-to-day life.
• Some fully fluorinated compounds are considered potential blood
substitutes in surgery.
 USES
• A chlorine-containing antibiotic,
chloramphenicol, produced by soil
microorganisms, is very effective for the
treatment of typhoid fever.

• They were previously used as

refrigerants and propellants.
 USES
• They are also used in fire
extinguishers.

• They were also used as cleansing agents

for creating cleaning formulas.
 SIGNIFICANCE
Haloalkanes or alkyl halides are used all over the world widely and
commercially. They have many alkyl halide properties, which help produce
other materials. However, some alkyl halides are toxic and harmful, limiting
or restricting their uses and production.

Presumably, without the presence of alkyl halides, some materials that we can
see and utilize in this world would be nonexistent.
 REFERENCES
https://byjus.com/jee/alkyl-halide/

https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Map
%3A_Organic_Chemistry_(Wade)_Complete_and_Semesters_I_and_II/Map
%3A_Organic_Chemistry_I_(Wade)/07%3A_Alkyl_Halides-
_Nucleophilic_Substitution_and_Elimination/7.04%3A_Reactions_of_Alkyl_Halides-
_Substitution_and_Elimination

https://chem.libretexts.org/Courses/Brevard_College/CHE_202%3A_Organic_Chemistry_II/
04%3A_Substitution_and_Elimination_reactions/4.01%3A_Alkyl_Halides_-
_Structure_and_Physical_Properties#:~:text=Alkyl%20halides%20can%20be%20classified,help
%20discern%20patterns%20and%20trends.