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Haloalkanes contain halogen atom(s) attached to the name haloalkanes and haloarenes derived by naming the alkyl group followed by the halide

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CHEMISTRY HALOALKANES AND HALOARENES

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Characteristics of Halo Compounds

Introduction

Hydrocarbons consisting halogen atoms are known as halo compounds. There are two types of halo compounds: Different Methods of Classification of Halogen Compounds

On the basis of the parent chain

a. If the halogen atom is attached to the alkyl group, then it is called haloalkane.

Structure: RX

b. If the halogen atom is attached to the aryl group, then it is called haloarene.

Structure:

Halo Compounds

Haloalkanes

Haloarenes

Alkyl hydrogen atom is replaced by halogen

atom. Haloalkane Aryl hydrogen atom is replaced by halogen atom. Haloarene The replacement of hydrogen atom(s) in a hydrocarbon, aliphatic or aromatic, by halogen atom(s) results in the formation of alkyl halide (haloalkane) and aryl halide (haloarene), respectively.

CHEMISTRY HALOALKANES AND HALOARENES

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On the basis of the type of halogen atoms

Depending on the types of halo atoms present, haloalkanes are classified as fluoro, chloro, bromo or iodo

compounds.

Examples:

CH3F, CH3Cl, CH3Br, CH3I

On the basis of the number of halogen atoms

Depending on the number of halogen atoms attached to the parent chain, haloalkanes are classified as follows:

Type Structure Example

Haloalkane

Monohaloalkane RX CH3Cl

C2H5Br

Dihaloalkane XRRX ClCH2CH2Cl

Trihaloalkane

Haloarene

Monohaloarene

Dihaloarene

Trihaloarene

CHEMISTRY HALOALKANES AND HALOARENES

www.topperlearning.com 4 Compounds containing sp3CX bond (X = F, Cl, Br, I) a. Alkyl halides or haloalkanes (RX) Monohalogen derivatives of alkanes are called alkyl halides, monohaloalkanes or simply haloalkanes.

Alkyl halides or monohaloalkanes are further classified as primary (1°), secondary (2°) and tertiary (3°)

according to how the halogen atom is attached to the primary, secondary and tertiary carbon atom,

respectively. b. Allylic halides

The halogen is linked to a sp3hybridised carbon atom which is next to a carboncarbon double bond, i.e.

to an allylic carbon. These may be further classified as 1°, 2° and 3°.

For example,

c. Benzylic halides These are compounds in which the halogen atom is bonded to a sp3-hybridised carbon atom next to an aromatic ring. These may be further classified as 1°, 2° and 3°.

For example,

CHEMISTRY HALOALKANES AND HALOARENES

www.topperlearning.com 5 d. Propargyl halides The halogen is attached to a sp3hybridised carbon atom which is next to a carboncarbon triple bond. These may be further classified as 1°, 2° and 3°. For example, Compounds containing Csp2X bond (X = F, Cl, Br, I)

These are of the following two types:

i. Vinylic halides: The halogen is attached to one of the carbon atoms of the carboncarbon double bond. For example, ii. Aryl halides: The halogen is directly attached to the aromatic ring.

Compounds containing sp3 CX bond

a. Vinylic halides

The halogen is attached to one of the carbon atoms of the carboncarbon double bond. For

example, b. Aryl halides The halogen is directly attached to the aromatic ring.

CHEMISTRY HALOALKANES AND HALOARENES

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Compounds containing CspX bond (X = F, Cl, Br, I)

The halogen is directly attached to one of the carbon atoms of the triple bond. For example,

Nomenclature of Halogen Compounds

Nomenclature of Haloalkanes (Alkyl halides)

a. Alkyl Halides In the common or trivial system, the monohalogen derivatives of alkanes are called alkyl halides. Their names are derived by naming the alkyl group followed by the name of the halogen as halide, i.e. fluoride, chloride, bromide or iodide. The complete name of any alkyl halide is always written as two separate words. In the IUPAC system, the monohalogen derivatives of alkanes are called haloalkanes.

Their individual names are derived by prefixing

chain alkane. In haloalkanes, numbering is always on the parent straight chain alkane. chain alkane. The numbering of the parent straight chain alkane is always done in such a way that the carbon atom carrying the halogen atom gets the lowest possible number. The IUPAC name of any monohalogen derivative of alkane is always written as one word.

Structural Formula Common Name IUPAC Name

CH3Cl

CH3CH2CH2CH2Cl

Methyl chloride

n-butyl chloride tert-butyl chloride

Chloromethane

1-chlorobutane

2-chloro-2-methylpropane

CHEMISTRY HALOALKANES AND HALOARENES

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Neopentyl chloride or Neoamyl

chloride

Isopentyl chloride or Isoamyl

chloride

1-chloro-2,2-dimethylpropane

1-chloro-3-methylbutane

b. Dihalogen Derivatives

These are of the following three types:

¾ Alkylidene dihalides

In the common system, dihaloalkanes in which two halogen atoms of the same type are present on the same carbon atom are called alkylidene dihalides. The positions on the same carbon atom are called germinal positions; therefore, alkylidene dihalides are also called germinal dihalides or gem-dihalides. In the IUPAC system, they are named dihaloalkanes, in which the position or the locant for the halogen, after being repeated twice, is prefixed to the name of the dihaloalkane. However, in case of dihalomethanes, the locants are not used.

Examples:

¾ Alkylene dihalides

In the common system, dihalogen derivatives of alkanes in which the two halogen atoms of the same type are present on the adjacent carbon atoms of the carbon chain are called alkylene dihalides.

The positions on the adjacent carbon atoms are called vicinal positions; therefore, alkylene

dihalides are also called vicinal dihalides or simply vic-dihalides.

Examples:

CHEMISTRY HALOALKANES AND HALOARENES

www.topperlearning.com 8 c. Polymethylene dihalides In the common system, dihalogen derivatives of alkanes in which the same two halogen atoms are present on the terminal carbon atoms, which are ĮȦ-positions of the carbon chain, are called polymethylene dihalides.

In the IUPAC system, the locants for the halogen atoms are prefixed to the name of the

dihaloalkane.

Examples:

d. Polyhaloalkanes In the common system, trihalomethanes and tetrahalomethanes are called haloforms and carbon tetrahalides, respectively.

Examples:

Nomenclature of Haloarenes (Aryl halides)

Haloarenes are the common and IUPAC names of aryl halides. For dihalogen derivatives, the prefixes o-, m-, p- are used in the common system, but in the IUPAC system, the numerical prefixes 1, 2; 1, 3 and 1, 4 are used. When the parent aromatic hydrocarbon carries a side chain or a substituent, the numbering of the carbon atoms of the ring begins with the substituent. If the parent hydrocarbon is benzene, then the numbering begins with the halogen atom. Polyhalogen derivatives have only IUPAC names in which the positions of halogens are indicated by Arabic numerals.

Structural Formula Common Name IUPAC Name

Chlorobenzene

o-chlorotoluene

Chlorobenzene

1-chloro-2-methylbenzene

CHEMISTRY HALOALKANES AND HALOARENES

www.topperlearning.com 9 p-dibromobenzene m-Dibromobenzene

1,4-Dibromobenzene

1,3-Dibromobenzene

Nature of CX Bond

Halogens are more electronegative than carbon; hence, the carbonhalogen bond is polarised. The carbon atom bears a partial positive charge, whereas the halogen atom bears a partial negative charge. As we go down the group, the size of the halogen atom increases down the group. Fluorine is the smallest and iodine is the largest in the table. As a result, the carbonhalogen bond length also increases from CF to CI.quotesdbs_dbs17.pdfusesText_23