CHAPTER 11 Alcohol Reactivity

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1 CHAPTER 11 Alcohol Reactivity 1

2 Summary Table

3 Oxidation: Adding O, Losing H

4 Chromic Acid (Cr(VI)) is a powerful oxidizing agent 4

5 Oxidation Mechanism

6 When Aldehydes are formed by Cr(VI) in water, they are are in equilibrium with their hydrates (geminal alcohols) These geminal alcohols undergo a second oxidation with Cr(VI) to form carboxylic acids quantitatively H H 2 O OH H O OH OH H H 2 CrO 4 OH H OH 2 OH O CrO 3 H OH O 6

7 PCC is a specialized Cr(VI) reagent that dissolves in dry solvents and thereby prevents hydrate formation. Primary alcohols stop at the aldehyde stage

8 Sodium Hypochlorite (NaOCl) Sodium hypochlorite (household bleach) can oxidize alcohols under relatively mild conditions without generating hazardous waste Pearson Education, Inc. Chapter 11 8

9 Swern Oxidation Dimethylsulfoxide (DMSO), with oxalyl chloride and hindered base, oxidizes 2 alcohols to ketones and 1 alcohols to aldehydes Pearson Education, Inc. Chapter 11 9

10 Swern Oxidation 10

11 Dess-Martin Periodinane (DMP) Can oxidize primary alcohols to aldehydes and secondary alcohols to ketones. The reaction with DMP takes place under mild conditions (room temperature, neutral ph) and gives excellent yields Pearson Education, Inc. Chapter 11 11

12 Reaction of Alcohols with HX 12

13 The stereochemistry of the product provides evidence of the mechanism 13

14 While 2 and 3 alcohols react with HCl via an SN1 mechanism, 1 alcohols react via SN2. Addition of ZnCl 2 facilitates the S N 2 reaction with the relatively weak nucleophile Cl

15 Carbocation Rearrangements: Unexpected products via rearrangement of the carbocation intermediate 15

16 The stereochemistry of the product provides evidence of the mechanism 16

17 Even Primary alcohols may undergo rearrangement. Alkyl and hydride shifts occur without the formation of primary carbocations when they are concerted with the loss of the leaving group: 17

18 Reaction with PBr 3 PBr 3 is an alternative to HBr. Advantages: Safer No rearrangement Fewer side reactions 18

19 Mechanism with PBr3

20 Reaction of Alcohols with Thionyl Chloride 2013 Pearson Education, Inc. Chapter 11 20

21 Dehydration of Alcohols Using POCl 3 and Pyridine

22 Reactions of Alcohols: Conversion of Alcohols to Alkyl sulfonates creates a good leaving group for subsequent displacement by an anionic nucleophile 22

23 Examples of SN2 Nucleophilic Attack on Alkyl Sulfonates: Inversion of the Chiral a-carbon 23

24 Dehydration of Alcohols: Review Alcohol dehydration generally takes place through the E1 mechanism. Rearrangements are possible. The rate of the reaction follows the same rate as the ease of formation of carbocations: 3 o > 2 o > 1 o. Primary alcohols rearrange, so this is not a good reaction for converting 1 alcohols into alkenes Pearson Education, Inc. Chapter 11 24

25 Unique Reactions of Diols Vicinal diols can undergo the following two reactions: Pinacol rearrangement Periodic acid cleavage

26 Pinacol Rearrangement Propose a Mechanism of this Rearrangement. Why does a rearrangement take place? 2013 Pearson Education, Inc. Chapter 11 26

27 Mechanism of the Pinacol Rearrangement 2013 Pearson Education, Inc. Chapter 11 27

28 Periodic Acid Cleavage of Glycols 2013 Pearson Education, Inc. Chapter 11 28

29 Esterification of Alcohols Fischer: Alcohol + carboxylic acid Tosylate esters Sulfate esters Nitrate esters Phosphate esters

30 Fischer Esterification The Fischer Esterification is a reversible reaction but yeilds are high when water is distilled as it forms, or alcohol is introduced in large excess 2013 Pearson Education, Inc. Chapter 11 30

31 Reaction of Alcohols with Acyl Chlorides The esterification reaction achieves better results by reacting the alcohol with an acyl chloride. The reaction is exothermic and produces the corresponding ester in high yields with only HCl as a by-product Pearson Education, Inc. Chapter 11 31

But in organic terms: Oxidation: loss of H 2 ; addition of O or O 2 ; addition of X 2 (halogens).

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