1. Chapter 8 Introduction to Alkyl Halides, Alcohols, Ethers, Thiols, and Sulfides

2. Alkyl Halides
Organic compounds containing at least one carbon-halogen bond (C-X)
X = F, Cl, Br, or I
X replaces an H
Properties and some uses
Fire-resistant solvents
Refrigerants
Pharmaceuticals and precursors

3. Nomenclature
Two systems:
Common
IUPAC

4. Common Naming Rules Generally used only for simple compounds
Identify the alkyl group and name it as a substituent
change the ending from “-ane” to “-yl,” if applicable
Identify the halide and name it
Leave a space between the two names from steps 1 and 2.

5. Other common names to learn:
Alkyl Halides
Other common names to learn:
8.1 Nomenclature

6. IUPAC Naming Rules
Identify the longest carbon chain and name it as the parent
Contains double or triple bond if present
Number the parent chain beginning at the end nearest any substituent (alkyl or halogen)
If more than one of the same kind of substituent is present, number each and use the Greek prefixes to indicate how many

7. If different substituents are equidistant from the ends of the parent chain, begin at the end nearer the substituent whose name comes first in the alphabet.

8. Problems
Name the following alkyl halides using common nomenclature
Name the following alkyl halides using IUPAC nomenclature:

9. Problems
CHCl3 is commonly known as chloroform. What is its IUPAC name?
Based on what you know from question #1, what are the common and IUPAC names for CHBr3, CHI3, and CHF3?

10. General Classifications
Alkyl halides can be classifed as methyl, primary, secondary, or tertiary based on the number of organic groups bonded to the halogen bearing carbon
8.1 Nomenclature

11. Problem
Draw 4-chloro-3,4-dimethyl-1-octene. Classify this alkyl halide based on degree of substitution.

12. Contain an OH group connected to a saturated (sp3-hybridized) Carbon
Alcohols
Contain an OH group connected to a saturated (sp3-hybridized) Carbon
Important solvents and synthesis intermediates
Methanol (Methyl Alcohol)
Common solvent
Fuel additive
Ethanol (Ethyl Alcohol)
Solvent
Fuel
Beverage
Isopropanol (Isopropyl Alcohol)
Rubbing alcohol
Disinfectant

13. Phenols
Compounds containing an OH group bonded to a carbon in a benzene ring
Building polycarbonates, epoxies, Bakelite, nylon, detergents and a large collection of drugs, herbicides and pharmaceuticals.
BPA
Eugenol

14. Glycols Compounds containing two or more hyrodoxyl (-OH) groups
Diol: contains two –OH groups
Geminal: OH’s are on the same carbon
Vicinal: OH’s are on adjacent carbons
General: OH’s located in non-geminal/non-vicinal positions
Ethylene Glycol
Resorcinol

15. General Classification

16. Nomenclature
Two types:
Common
IUPAC

17. Common Naming Rules Used for simple and common alcohols
Identify the alkyl group to which the hydroxyl group is attached and name this as a substituent
Ethane  Ethyl
Add the word “Alcohol”

18. IUPAC Naming Rules
Select the longest carbon chain containing the hydroxyl group, and derive the parent name by replacing the “-e” ending of the corresponding alkane with “-ol “
Number the chain from the end nearest to the hydroxyl group
Number substituents according to position on chain and then list them in alphabetical order as usual
2-chloro-5-methyl-1-hexanol
Or 2-chloro-5-methylhexan-1-ol

19. If stereochemistry is known, indicate it
If there are more than one hydroxyl groups, use Greek prefixes to indicate how many
Do not drop the final e of the alkane
If stereochemistry is known, indicate it

20. Naming Phenols
Use “phenol” (the French name for benzene) as the parent hydrocarbon name, not benzene
Name substituents on aromatic ring by their position from OH

21. Name the following molecules:
Problems
Name the following molecules:
Classify the first two molecules above based on level of substitution (1°, 2°, 3° alcohol)
Draw the following molecules
1,2,3-propanetriol
2-ethyl-3-methylphenol

22. Thiols
Compounds that contain a carbon bonded to a sulfhydryl group (-SH)
Sulfur analogs of alcohols
R-SH vs. R-OH
Stinky molecules
Also known as “Mercaptans”
The –SH group is also called a “mercapto” group
Ethanethiol vs Ethanol

23. Nomenclature of Thiols
Common:
Named in the same fashion as alcohols
The word mercaptan replaces alcohol in the name of the equivalent alcohol compound
Example: CH3SH would be methyl mercaptan, just as CH3OH is called methyl alcohol.
Methyl mercaptan
Methyl Alcohol

24. IUPAC
Identify the longest carbon chain containing the sulfhydryl group. Name this chain and add “thiol” to the end (no space).
Number the chain so that the carbon connected to the –SH group has the lowest number possible
Name and number all of the substituents and place them, in alphabetical order, in front of the parent chain name.
2-hexanethiol
2-ethyl-1-hexanethiol

25. Name the following compounds:
Problems
Name the following compounds:
Draw:
3,3-dimethyl-1-butanethiol
2-ethylcyclohexanethiol
Trans-3-heptene-2-thiol

26. Hmmmmm….

27. Principle Group and Principle Chain
Principle Group: the functional group upon which the name of a molecule is based
Cited as the suffix in the name
Example: Pentanol
Have priorities in a molecule
All other substituents are cited as prefixes (except multiple bonds)
Carboxylic acid > anhydride > ester > acid halide > amide > nitrile > aldehyde > ketone > alcohol/phenol > thiol > amine
8.1 Nomenclature 27

28. Identify the principle group (e.g., -OH > -SH)
Identify the principle chain
The carbon chain on which is the name is based
Priorities for picking the principle chain:
The carbon chain with the greatest number of principle groups
The carbon chain with the greatest number of double and triple bonds
Of greatest length
With the greatest number of other substituents

29. Principle Group and Principle Chain
Number the carbons of the principle chain giving the lowest numbers:
For the principle groups
For multiple bonds (C=C > CC)
For other substituents
For the substituent cited first in the name
8.1 Nomenclature 29

30. Principle Group and Principle Chain
Begin construction of the name with the name of the hydrocarbon corresponding to the principle chain
Cite principle group by suffix and number
Will be last number in molecular name
If there is no principle group, name the compound as a substituted hydrocarbon
Cite the names and numbers of other substituents in alphabetical order
8.1 Nomenclature 30

31. Problems
Name the following compounds: