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

Alcohols IR 1050 690 760

Acidity of Alcohols and Phenols Chem Act 20

Which is most acidic and why?

Problem 17.65

Problem 17.65

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

Oxidation

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

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

Chapter 18 Thiols, Ethers, Sulfides

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

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

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

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

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

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

17.63

17.64

17.66

Problems 18.29 and 18.41

OrganoSulfur Chemistry

Problem 16.73

Problem 18.55