1. ORGANIC HALOGEN COMPOUNDS

2. Uses of Halogen Compounds
DDT: chlorinated insecticides. These create problems because they can be absorbed into fatty tissue.
Chloform
Saran, teflon, pvc, neoprene rubber

3. Alkyl Halides - Properties
Alkyl halides: alkanes molecule with a halogen replaces a hydrogen.
Further described as primary, secondary, or tertiary.
Organic halides have boiling points that increase with molecular weight.
C3H7Cl > C2H5Cl > CH2Cl
F<Cl<Br<I
Densities are greater than water.
They are insoluble in water.

4. Classes of Organic Halogens
Alkyl halides
Vinyl halides
Allylic halides
Benzylic halides

5. Nomenclature IUPAC: Use prefixes fluoro,chloro, bromo, iodo
Common: alkyl group name procedes the name of the halide.

6. Alcohols, Phenols, Ethers
Alcohols, phenols and ethers are derivatives of water in which one or both hydrogens are replaced by a hydrocarbon group.
Alcohol: alkane in which a hydrogen is replaced with -OH. (hydroxyl group)
Phenol: aromatic ring bonded to –OH.
Ether: R1 – O – R2

7. Alcohols can be described as primary, secondary, or tertiary.

8. IUPAC Nomenclature
Saturated Alcohols: based on name of longest chain. Change –e to –ol.
When necessary, the position of the alcohol functional group is described by numbers.
Carbon chain is numbered to give the alcohol group lowest possible number.
Compounds containing two or more alcohol groups are named as diols, triols, etc. with a positional number assigned to each –OH group.

9. Unsaturated Alcohol: Change –ane to -ene or –yne
Unsaturated Alcohol: Change –ane to -ene or –yne. Alcohol takes precedence in numbering chain.
Complete the name by naming all their groups by prefixes with their numerical positions.

10. IUPAC Nomenclature of Ethers
First find the longest continuous chain of carbon atoms. The Substituents attached to this chain can be pictured as an alkyl group containing an oxygen. Referred to as alkoxy group.
These groups are named as prefixes and their position designated by number.

11. IUPAC Nomenclature of Phenols
Name according to the rules for a substituted benzene ring, except the family name is phenol.
The –OH is number 1.

12. Common Names
Alcohols and ethers are frequently referred to by common names.
Alkyl group or groups connected to the oxygen are named first in alphabetical order, followed by the class of compound, alcohol or ether.

13. Physical Properties
Melting points and boiling points of alcohols and ethers generally increase with increasing molecular weights within a homologous series.
Alcohols exhibit unusually high boiling points because of hydrogen bonding.
Low-molecular weight alcohols are water soluble.
Solubility drops off significantly with butanol.

14. Uses of Alcohols, Ethers, and Phenols
Methyl, ethyl, isopropyl alcohols are most common.
Polyhydric alcohols are alcohol with more than one hydroxy group.
Ethylene glycol (1,2-ethanediol) is used in antifreeze.
Glycerol (1,2,3-propanetriol) is a sweet, syrupy liquid obtained as a by product of soap manufacturing.

15. October 2002, December 2002

16. Diethyl ether, CH3CH2OCH2CH3, is used as a general anesthetic.
Glycerol can be converted into nitroglyerin by treatment with nitric acid and sulfurinc acid.
Diethyl ether, CH3CH2OCH2CH3, is used as a general anesthetic.
Phenols have four medicinal uses:
Ability to act as antiseptic, disinfectant
Ability to act as a local anesthetic
Skin irritancy
Toxicity when ingested.

17. Antioxidants and Photographic developers
Tetrahydrocannabinol