1. Chemistry 350 Organic Chemistry II Spring, 2015 2/18/15
Chemistry 350
Organic Chemistry II
Spring, 2015
2/18/15
Chapter 17 Phenols and Alcohols
Handout and Chem Act 20
Next week
3) Chapter 18 Ethers, Epoxides, Sulfides

2. Alcohols IR
1050
690
760

3. Acidity of Alcohols and Phenols Chem Act 20

4. Which is most acidic and why?

5. Problem 17.65

6. Problem 17.65

7. NaH K (metal) NaNH2 NaOH CH3MgBr They all can be used
Which reagent cannot be used to stoichometrically prepare a tertiary alkoxide from the corresponding alcohol?
NaH
K (metal)
NaNH2
NaOH
CH3MgBr
They all can be used

8. Oxidation

9. What is the product of the following reaction?1. 2. 3. 4. 1 2 3 4

10. What is the major product of the following reaction?1. 2. 3. 4. 5. 1 2 3 4 5

12. Chapter 18 Thiols, Ethers, Sulfides

13. What is the major product of the following reaction?1. 2. 3. 4. 1 2 3 4

14. Which is the best combination of reactants to prepare phenyl methyl ether by Williamson synthesis?
phenoxide and methyl iodide
methoxide and phenyl iodide
methoxide and phenyl tosylate
phenol, methanol and strong acid as a catalyst
all these will work well

15. What is the major organic product of the reaction shown below?1. 2. 3. 5. 4. 1 2 3 4 5

16. What is the product of the following sequence of reactions?1. 2. 3. 4. 5. 1 2 3 4 5

17. 17.31 2-phenylethanol into (a) styrene (b) phenylacetaldehyde
(c) phenylacetic acid
(d) Benzoic acid
(e) Ethylbenzene
(f) Benzaldehyde
(g) 1-phenylethanol
(h) 1-bromo-2-phenylethane

18. 17.32 1-phenylethanol into Acetophenone (b) Benzyl alcohol
(c) m-Bromobenzoic acid
(d) 2-phenyl-2-propanol

19. 17.63

20. 17.64

21. 17.66

22. Problems and 18.41

23. OrganoSulfur Chemistry

24. Problem 16.73

25. Problem 18.55