1. TOPIC 10. ALCOHOLS AND ETHERS (chapter 11)

2. OBJECTIVES 1. Name and describe structure of alcohols and ethers.
2. Describe mechanisms of reactions of alcohols and ethers.
3. Predict the product(s) of reactions of alcohols and ethers.
4. Provide syntheses of alcohols and ethers.

3. EXAMPLES, STRUCTURE, NOMENCLATURE & PHYSICAL PROPERTIES
Prob:
Alcohols: Nomenclature
Trivial names

4. Ethers: Nomenclature

5. Physical Properties
Alcohols have higher boiling points than ethers with same formula
Boiling point increases with molecular weight
Et2O: volatile, flammable, anesthetic; oxidizes slowly in air to give explosive peroxide.
tBuOMe (MTBE): controversial oxygenated fuel additive

6. SYNTHESIS OF ALCOHOLS Review: Acid Catalyzed Hydration of Alkenes
S1.4-7 Prob:11.33, 35(c-e),40,46
Review: Acid Catalyzed Hydration of Alkenes
Intermediate carbocations can rearrange.

7. Oxymercuration-Demercuration of alkenes
e.g.,
Step 1: Oxymercuration
Step 2: Demercuration

8. Mechanism

9. Hydroboration-Oxidation of Alkenes: Anti-Markovnikov
Hydration of Alkenes
e.g.,
Step 1: Hydroboration
Step 2: Oxidation

10. Mechanism: Regiochemistry

11. Stereochemistry

12. ALCOHOLS AS ACIDS AND BASES
Alcohols are weak acids and weak bases. However, acid-base chemistry is important in activating the electrophilic and nucleophilic character of alcohols, respectively.

13. MESYLATES AND TOSYLATES IN SN2 REACTIONS
R’ = Me: mesylate (Ms) methylphenyl: tosylate (Ts)

14. CONVERSION OF ALCOHOLS TO ALKYL HALIDES
Alcohol + H-Hal
3o Alcohols: SN1

15. 1o Alcohols: SN2

16. Other reagents

17. SYNTHESIS AND REACTIONS OF ETHERS
S Prob:11.38
Dehydration of Alcohols

18. Acid Catalyzed Hydrolysis of Ethers

20. Williamson Ether Synthesis

21. Designing Williamson Ether Syntheses
You could suggest making either C-O bond of the ether.

22. EPOXIDES
S1.16,18 Prob 11.38
Synthesis
MMPP
mCPBA

23. Nucleophilic Ring-opening of Epoxides
Stereochemistry

24. Regiochemistry

26. MULTISTEP SYNTHESES
Prob 11.36,42, 44,45,47
Problem: Propose a synthesis of 1-methyl-1,2-cyclopenanediol (with the two hydroxy groups trans to one another) from methylcyclopentane.

27. Problem: An insect physiologist required hex-4Z-en-3-ol for the study of insect pheromones. Propose a synthesis of hex-4Z-en-3-ol from pentene

28. CHAPTER 11 ON FINAL Types of Questions Preparing for Final
- Describe mechanisms of reactions involving alcohols and ethers
- Predict the products of reactions involving alcohols and ethers
- Propose syntheses of alcohols and ethers
The problems in the book are good examples of the types of problems on the exam.
Preparing for Final
- Work as many problems as possible.
- Work in groups.
- Do the “Learning Group Problem” at the end of the chapter.

29. THE LONG AND WINDING ROAD…..
Where we have been:
Description of the Structure of Organic Molecules
Description of reaction pathways
Substitution at sp3 carbons bearing leaving groups
Elimination from sp3 carbons bearing leaving groups
Addition to alkenes and alkynes
Development of multistep (2-3 step) Synthetic Pathways
Determination of Structure

30. …..GOES ON FOREVER Where we are going…
CHEM 2312: Organic Chemistry – 2
Preparing compounds with an impact on human health and nutrition, the economy, and your well-being.
Particular emphasis on the chemistry of benzene rings, carbonyl-containing functional groups, C-C bond formation to prepare complex (useful!) organic molecules, sex, drugs, and rock and roll.

31. That's All, Folks