1. Chapter 9 Reactions of Alcohols, Ethers, Epoxides, Amines, and Thiols
Paula Yurkanis Bruice
University of California,
Santa Barbara

2. Contents of Chapter 9 Naming Alcohols
Substitution and Dehydration of Alcohols
Oxidation of Alcohols
Naming Ethers
Epoxides
Skip Thiols and SAM Methylation
Chapter 10

3. Naming Alcohols Find longest carbon chain containing the alcohol.
OH gives attached carbon lowest possible number.
Break ties with other substituents if necessary.
Substituents are listed in alphabetical order.
Chapter 10

4. Examples Determine longest chain with OH
Blue chain is longer; however,
Red chain contains OH
Notice that numbering starts at alcohol group
2. Name: 2-propyl-1-hexanol
Chapter 10

5. Examples
Chapter 10

6. Conversion of Alcohols to Alkyl Halides
Hydrogen halide reactions can be SN1 or SN2
Chapter 10

7. Mechanism of Substitution
Secondary and tertiary alcohols undergo SN1 reaction.
Chapter 10

8. Mechanism of Substitution
Primary alcohols undergo SN2 reaction. Primary carbocations are too unstable to be formed.
Attack from back-side
Chapter 10

9. Dehydration of Alcohols
Zaitsev’s Rule is followed whenever possible
Chapter 10

10. Dehydration of Alcohols
Chapter 10

11. Cr6+ Oxidation of Alcohols
Acidic hexavalent chromium removes all  H’s makes C-O bonds
PCC removes only one  H and makes an aldehyde from a 10 alcohol
Chapter 10

12. Cr6+ Oxidation of Alcohols
Chapter 10

13. Oxidation by Hypochlorous Acid (HOCl)

14. Nomenclature of Ethers
Common Name: Name of alkyl substituents followed by “ether”
methyl isopropyl ether
methyl ethyl ether
IUPAC
Parent alkyl compound with RO substituent. “-yl” is then replaced by “oxy”
2-methoxy-butane
1-ethoxy-2-methylpropane
Chapter 10

15. Substitution Reactions of Ethers
Ethers can be cleaved only with HI and HBr, not HCl
SN1 and SN2 reactions give opposite regioselectivity; H goes on bulky C in SN2, and less-hindered in SN1
Chapter 10

16. Epoxides
Chapter 10