1. Organic halides

2. Learning Objectives
In this chapter will discusses the following topics and by the end of this chapter the students will:
Recognize the structure and classes of alkyl halides
Know the common names and understand the IUPAC rules for nomenclature of
halo compounds
Understand the physical properties of halo compounds (solubility and boiling points)
Know the different methods used in preparation of halo compounds
Know the reactions of halo compounds; nucleophilic substitution, elimination, reduction reactions of Grignard reagents and know the previously disused methods of reducing alkyl halides (Chapter-1)

3. Organic Halides Source &uses:
1- Rare in nature produced by microorganisms.
2- used (herbicides, detergent , insecticide)
3- intermediat for synthesis.
According to hydrocarbon gp.
1-Alkyl halides( R-X):
2-Allylic halides
3-Vinylic halides
4-Benzylic halides
5-Aryl halides

4. Classes and Names of Halogen Compounds
145 Chem
Alkyl Halides
Classes and Names of Halogen Compounds
CH3-X and R-CH2-X : Primary alkyl halide.
(R)2-CH-X : Secondary alkyl halide.
(R)3-C-X : Tertiary alkyl halide.
According to hydrocarbon gp.
1-Alkyl halides( R-X) has a halogen atom bonded to one sp3 hybrid C atom
2-Allylic halides has a halogen atom bonded to one sp3 hybrid C atom
3-Vinylic halides has a halogen atom bonded to one sp2 hybrid C atom
4-Benzylic halides has a halogen atom bonded to Carbone one away from aromatic ring
5-Aryl halides has a halogen atom bonded directly to an aromatic ring
145 Chem

5. Nomenclature OF Alkyl halides
IUPAC names derived from the names of parent organic compound (alkane or alkene or alkyne or alcohol or aldehydes and so on) with a prefix indicating halogens and their positions.
Common names derived from the corresponding alkyl group followed by the name of halogen atom.
CH3-Cl CH3-CH2-Br (CH3)2-CH-F
Common Methyl Chloride Ethyl bromide Isopropyl fluoride
IUPAC Chloromethane Bromoethane Fluoropropane
Class ° ° °
Common Cyclohexyl Iodide t-Butyl bromide Methylcyclopentyl chloride
IUPAC Iodocyclohexane Bromo-2- methylpropane Chloro-1-methyl cyclopentane
Class ° ° °

6. 1-Alkyl halides( R-X): 1,2 & 3(no H attached)
CH3Cl CH3CH2CH2Br CH3CHFCH3
Comm.: Methyl Chloride n- Propyl bromide Isopropyl fluoride
IUPAC: Chloromethane Bromo propane Fluoropropane
Class   
Cyclo hexyl iodide Methyl cyclopentyl chloride t-Butyl romide
I Iodocyclohexane Chloro-1-methylcyclopentane 2-Bromo-2-methylpropane
Class:   

7. 2- Vinylic halides 3- Allyl halides 4-Benzylic halides:
C=C-C- X
C=C-X
CH2=CHCH2Cl
Allyl chloride
3-Chloro-1-propene
CH2=CHBr
Vinyl bromide
Bromoethene
3-Chlorocyclopentene
4-Benzylic halides:
Ar-C-X ( halogen one carbon away from aromatic ring)
COM. Benzyl Chloride
IUPAC Chloromethyl benzene
5-Aryl halides:
Ar-X (X directly attached to  )
Chlorobenzene p-Bromo toluene

8. Exercise

9. Physical Properties
Solubility : All organic halides are insoluble in water and soluble in common organic solvents.
Boiling point : The boiling points increases with increasing in molecular weights.
Therefore, the boiling points increases in the order F < Cl < Br < I.
Alkyl halides have higher melting points than alkanes, alkenes, alkynes because of 1. Polarity
2. Molecular weight

10. Preparation Of Halocompounds
1- Direct Halogenation Of Hydrocarbons
Halogenation of alkanes
b) Halogenation of alkenes

11. c) Halogenation of alkynes
d) Halogenation of alkyl benzene

12. 2- Halogenation Of Alcohols

13. Reactions of Organic Halides
1- Nucleophilic Substitution Reactions

14. 2- Elimination Reactions:
Alkyl halides can lose HX molecule to give an alkene.
e.g.2
If the haloalkane is unsymmetrical (e.g. 2-bromobutane or 2-bromopentane) a mixture of isomeric alkene products is obtained.

15. 3) Formation of Grignard reagent and its reactions
Reactions of Grignard reagent

16. 4- Reduction of alkyl halides
a) Reduction by Zinc metal and acids or by metal hydrides
b) Reduction by sodium metal (coupling reaction)
c) Reduction using lithium dialkyl cuprate

17. Exercise

18. Exercise
Stating from the following compounds prepare the desired products:

19. Thank You for your kind attention !
Questions?