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Alkyl Halides

Nucleophilic Aliphatic Substitution

and Elimination

Dr. hudasalehabood

For 1stStage Students

Alkyl halides

Alkyl halides are organic molecules containing a

halogen atom bonded to an sp3 hybridized carbon atom. ͻ Alkyl halides are classified as primary (1Σ), secondary (2Σ), or tertiary (3Σ), depending on the number of carbons bonded to the carbon with the halogen atom.

ͻ The halogen atom in halides is often denoted

by the symbol ͞X"

General structure of alkyl halides

R-X (X= F,Cl, Br, I)

Ris any simple alkyl or substituted alkyl group

Classification

Alkyl halides can be classified according to the class of the carbon that the halogen is attached to.

Primary Secondary Tertiary

There are other types of organic halides, These include: ͻ Vinyl halides have a halogen atom (X) bonded to a C=C double bond. ͻ Aryl halides have a halogen atom bonded to a benzene ring. ͻAllylic halides have X bonded to the carbon atom adjacent to a C=C double bond. ͻ Benzylichalides have X bonded to the carbon atom adjacent to a benzene ring.

Examples of 1°, 2°, and 3°alkyl halides

Four types of organic halides (RX) haǀing y near a ʋ bond

Nomenclature

Common name:replacing -aneof alkane by -yland

follow by halidefor longest chain.

IUPAC name:prefixing Halo-followed by alkane, as

in alkanes.

Common names

Common names are often used for simple

alkyl halides. To give a common name:

1-Name all the carbon atoms for longest

chain of the molecule as a separate alkyl group by replacing aneof alkane by yl.

2-Name the halogen (replace to halide) that

bonded to the alkyl group .

Combine the names of the alkyl group and

halide, separating the words with a space.

Anesthetic

2-Bromo-2-chloro-1,1,1-trifluoro-ethane

Example of drugs

Common nameStructure IUPAC nameNo. of C atom

Methyl bromideBromomethane

1

Ethyl bromideBromoethane

2 n-Propyl bromide1-Bromopropane

3Isopropyl

bromide

2-Bromopropane

H3C Br BrBr Br n-Butyl bromide1-Bromobutane sec-Butyl bromide2-Bromobutane

Isobutyl bromide1-Bromo-2-methylpropane

tert-Butyl bromide2-Bromo-2-methylpropane Br Br Br Br

CH3CHCH2CH3

Cl

CH3CH2CH2CHCH2CH2CH3

CH2CH2F

CH3CHCH2CH2CH2CHCH2CH2CH3

BrCH3 Q/ Give the structure and IUPAC name of n-, iso-, sec-, tert- and neo-pentylchloride. Q/ Give the common and IUPAC name of the following:

Physical properties of alkyl

halide ofcarbons. n-Pentane (36oC) n-Pentylchloride (108 oC) For a given alkyl group, the boiling point increases with increasing atomic weight of the halogen, so that a fluoride is the lowest boiling, an iodide the highest boiling. For a given halogen, b.p. rises with increasing number of carbon atoms. n-Propyl chloride (47) n-Butyl chloride (78.5)

The branching lowers the b.p.

n-Butyl bromide (102) sec-Butyl bromide (91) solvents. Iodo, bromo, and polychlorocompounds are more dense than water.

Preparation

1-From alcohols

Alcohols react with hydrogen halides or phosphorus halides.

2-Halogenation of certain hydrocarbons.

Under the influence of ultraviolet light, or at 250-400, chlorine or bromine converts alkanesinto chloroalkanes(alkyl chlorides) or bromoalkanes(alkyl bromides.

3-Addition of hydrogen halides to alkenes.

Markovnikov'srule

An alkene is converted by hydrogen chloride, hydrogen bromide, or hydrogen iodide into the corresponding alkyl halide.

4-Addition of halogens to alkenes and alkynes

Alkenes are readily converted by chlorine or bromine into saturated compounds that contain two atoms of halogen attached to adjacent carbons.

5-Halide exchange (Finkelstein reaction).

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