Chapter 13 Outline: Alcohols & Phenols
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1 Chapter 13 Outline: Alcohols & Phenols Review Nomenclature, Structure, Physical Properties, and Acidity on your own, (pp ); this material reviews things we have done previously. 1. Preparation of Alcohols a) Substitution chapter 7 b) Addition to alkenes chapter 9 c) Reduction of carbonyls what is oxidation reduction? 2. Preparation of Diols 3. Grignard Reagents 4. Protection of Alcohols 5. Reactions of Alcohols a) Reaction with HX b) Reaction with PBr 3 c) Reaction with SOCl 2 /py d) Reaction with TsCl/py e) Acid catalyzed dehydration (H 3 PO 4 or TsCl/base) f) Dehydration with POCl3/py g) Oxidation of alcohols h) Oxidation of phenols You should do all the problems in the textbook, but these are some suggested homework problems: 13.30, 13.31, 13.33, 13.35, , 13.44, , 13.51, Page 1 of 30
2 1. Preparation of Alcohols A. Substitution Reactions B. Addition to Alkenes C. Reduction of Carbonyls what is reduction? Page 2 of 30
3 What is oxidation reduction? One direction of a reaction will be oxidation and the opposite direction will be reduction: Oxidation: loss of C H, the gain of C Z, or both Reduction: the gain of C H, the loss of C Z, or both Page 3 of 30
4 C. Reduction of Carbonyls (hydride reagents) Page 4 of 30
5 Comparing LAH to NaBH 4 LAH is strong enough to also reduce esters and carboxylic acids, whereas NaBH 4 is generally not. To reduce an ester, two hydride equivalents are needed. Mechanism? O 1. xs LAH R OMe 2. H 2 O Page 5 of 30
6 2. Preparation of Diols Perform a reduction twice of th reaction we just did! Page 6 of 30
7 3. Grignard Reagents Grignard reagents are often used in the synthesis of alcohols. To form a Grignard, an alkyl halide is treated with Mg metal. How does the oxidation state of the carbon change upon forming the Grignard? Will it act as an acid, base, electrophile, nucleophile, etc.? Because the Grignard is both a strong base and a strong nucleophile, care must be taken to protect it from exposure to water. What solvent is appropriate for these reactions? Page 7 of 30
8 Mechanism? O Ph CH H 2 O MgCl Page 8 of 30
9 Synthesis: Design a synthesis for the following molecules starting from an alkyl halide and a carbonyl, each having five carbons or less. Page 9 of 30
10 4. Protection of Alcohols Consider the reaction below. WHY won t it work? Strategy for protecting alcohols: Page 10 of 30
11 Page 11 of 30
12 5. Reactions of Alcohols how to make a good leaving group? All of these reactions you will learn in this chapters have one common theme converting the OH group into a good, stable leaving group!! a. ROH reaction with HCl, HBr & HI (converting a ROH RX) 1 o ROH react through an S N 2 mechanism: Page 12 of 30
13 2 o /3 o ROH react through an S N 1 mechanism: Page 13 of 30
14 b. Reaction with PX 3, X = Cl, Br (converting a ROH RBr) Reaction Observations: o This reaction can only be used with 1 o and 2 o ROH only o Reaction always occurs with inversion of configuration. o What substitution mechanism does this support? Mechanism? Page 14 of 30
15 c. Reaction with Thionyl Halide (SOX 2, X = Cl, Br) (converting a ROH RX) Reaction Observations: o This reaction can only be used with 1 o and 2 o ROH only o Reaction always occurs with inversion of configuration. o What substitution mechanism does this support? Mechanism? O OH Cl S Cl Page 15 of 30
16 d. Formation of Tosylates to provide good leaving groups What is important about this? Sulfonate anions are weak bases, making them VERY GOOD leaving groups. Look at H 2 SO 4 and consider its acidity: Since alcohols make poor leaving groups, reacting them with sulfonyl chlorides converts them into better leaving groups. Most common sulfonyl chloride reagents: TsCl (Para toluene sulfonyl chloride) MsCl (mesyl chloride) Page 16 of 30
17 How do these reactions work overall? It s a two step reaction, (1) react the desired alcohol with the tosyl chloride without inversion, and (2) react it with the nucleophile leading to inversion of configuration: Page 17 of 30
18 e. Acid catalyzed Dehydration of Alcohols to Alkenes (ß elimination reaction) Compare to: E1 mechanism is observed for 2 o and 3 o ROHs: OH H 3 PO 4,H 2 O heat How do you think the mechanism differs for a 1 o ROH? Page 18 of 30
19 Provide the mechanism for the following transformation: Page 19 of 30
20 f. Dehydration of ROH using POCl 3 & Pyridine (converting a ROH alkene) Mechanism? This mechanism is known to go through an E2 mechanism. Page 20 of 30
21 g. Oxidation of Alcohols (no mechanism to know) Primary alcohols are oxidized to either aldehydes or carboxylic acids, depending on the reagent employed: Secondary alcohols are oxidized to ketones. Tertiary alcohols cannot be oxidized why? Common oxidizing reagents are: Page 21 of 30
22 1 o ROH give different products depending on the reagent used: OH PCC OH K 2 Cr 2 O 7 H 2 SO 4,H 2 O 2 o ROH give same products regardless of the reagent used: OH PCC or K 2 Cr 2 O 7 H 2 SO 4,H 2 O Provide the organic product for the following reactions. You do not need to balance the byproducts of the reaction. Page 22 of 30
23 h. Oxidation of Phenols Phenol is even more readily oxidized than primary or secondary alcohols. Page 23 of 30
24 Alcohol Reactions. Provide correct organic product(s) and the mechanism for the following reactions. If stereochemistry pertains, ensure it is clearly demonstrated. If there is more than one product, then circle the major product. OH POCl 3 pyridine Mechanism? Page 24 of 30
25 OH HBr Mechanism? Page 25 of 30
26 OH SOCl 2 pyridine Mechanism? Page 26 of 30
27 O 1. LAH Ph H 2. H 2 O Page 27 of 30
28 Provide viable steps to bring about the following transformation. Page 28 of 30
29 Provide viable steps to bring about the following transformation. Page 29 of 30
30 Provide viable steps to bring about the following transformation. Page 30 of 30
But in organic terms: Oxidation: loss of H 2 ; addition of O or O 2 ; addition of X 2 (halogens).
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