21.1 Introduction Carboxylic Acids

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1 21.1 Introduction Carboxylic Acids Carboxylic acids are abundant in nature and in pharmaceuticals. Klein, Organic Chemistry 1e 21-1

2 The US produces over 2.5 million tons of acetic acid per year, which is primarily used to produce vinyl acetate. Vinyl acetate is used in paints and adhesives. Carboxylic acid derivatives, such as vinyl acetate, are very common, and they play a central role in organic chemistry. Klein, Organic Chemistry 1e 21-2

3 21.2 Nomenclature of Carboxylic Acids Monocarboxylic acids are named with the suffix oic acid. The carbon of the carboxylic acid moiety is assigned the locant position 1. Klein, Organic Chemistry 1e 21-3

4 When the carboxylic acid group is attached to a ring, it is named as an alkane carboxylic acid. There are also many common names for carboxylic acids. Klein, Organic Chemistry 1e 21-4

5 Dicarboxylic acids are named with the suffix dioic acid. There are also many common names for dicarboxylic acids: Klein, Organic Chemistry 1e 21-5

6 21.3 Structure/ Properties of Carboxylic Acids The carbon atom of the carboxylic acid has a trigonal planar geometry. The acid moiety is capable of strong hydrogen (H ) bonding including H-bonding between acid pairs. As a result, carboxylic acids generally have high boiling points. Consider the BPs of acetic acid (118 C) and isopropanol (82 C). Klein, Organic Chemistry 1e 21-6

7 Carboxylate ions end in the suffix oate. Compounds that end in the suffix oate are often found in food ingredient lists as preservatives. NaOH is a strong base, so it is capable of reacting 100% with a carboxylic acid. Klein, Organic Chemistry 1e 21-7

8 In water, the equilibrium generally favors the acid. pk a values mostly range between 4 and 5. What is pk a? Klein, Organic Chemistry 1e 21-8

9 How does the pk a value for a carboxylic acid compare to a strong acid like HCl, or a very weak acid like ethanol? H Cl pk a = -7 How can induction and resonance be used to explain the acidity of a carboxylic acid? Klein, Organic Chemistry 1e 21-9

10 Let s examine the equilibrium between the carboxylic acid and the carboxylate at physiological ph (7.3). The acid and the conjugate base make a buffer. HOW? Recall that the Henderson-Hasselbalch equation can be used to calculate the ph of a buffer: Assuming the pk a is 4.3, calculate the ratio of carboxylate/acid. Klein, Organic Chemistry 1e 21-10

11 Many biomolecules exhibit carboxylic acid moieties. Biomolecules such as pyruvic acid exist primarily as the carboxylate under physiological conditions. Klein, Organic Chemistry 1e 21-11

12 Electron withdrawing substituents have a great effect on acidity. Wiley & Sons, Inc. Klein, Organic Chemistry 1e 21-12

13 Electron withdrawing substituents affect benzoic acid as well. Klein, Organic Chemistry 1e 21-13

14 21.4 Preparation of Carboxylic Acids Klein, Organic Chemistry 1e 21-14

15 Two new ways to make carboxylic acids: 1. The hydrolysis of a nitrile can produce a carboxylic acid. The mechanism will be discussed later. Carboxylic acids can be made from alkyl halides using a two-step process. Klein, Organic Chemistry 1e 21-15

16 2. Carboxylation of a Grignard reaction can be achieved using CO 2. Klein, Organic Chemistry 1e 21-16

17 Which of the following will undergo a downhill acid base reaction when exposed to an amine such as ammonia (NH 3 )? 1. I only 2. II only 3. I and II I and III 4. I and IV 5. I, II, and IV 6. All of them 7. None of them 8. Not sure

18 1. No errors 2. 1 error 3. 2 errors 4. 3 or more errors 5. Not sure 6. Need more time CTQ 7?

19 21.10 Preparation of Esters Fischer esterification combines a carboxylic acid and an alcohol using an acid catalyst. Klein, Organic Chemistry 1e 21-19

20 Each step of the Fischer esterification mechanism is equilibrium. Under acidic conditions, ( ) charges are avoided. Klein, Organic Chemistry 1e 21-20

21 The overall Fischer esterification reaction is an equilibrium process. How might you use Le Châtelier s principle to favor products? How might you use Le Châtelier's principle to favor reactants? Klein, Organic Chemistry 1e 21-21

22 Which reactions will NOT give a significant amount of product? excess I. O H 3 C NH 2 O H 2 O II. H CH 3 O N H III. C 6 H 5 O O H H 3 C H N H 2 SO 4 CH 2 CH 3 excess C 6 H 5 O N H 2 O IV. O O O O H H LiAlH 4 excess H 3 O O O NH 3 NH O 4 H H 2 O excess excess V. O O VI. O Et OH Et OH H Et H O Et ONa O O H 2 SO 4 O O Et H 2 O 1. I, II, and III 2. I, II, and IV 3. I, III, and IV 4. I, III, and V 5. II, III, and IV 6. I, II, and V 7. IV, V, and VI 8. Not sure 9. Need more time 8. Not sure 9. Need more time

23 21.11 Reactions of Esters Esters can undergo hydrolysis in the presence of aqueous hydroxide (SAPONIFICATION). Predict the last steps in the mechanism. To produce a carboxylic acid, H 3 O + must be added at the end. WHY? Klein, Organic Chemistry 1e 21-23

24 SAPONIFICATION is an equilibrium process. Analyze the reversibility of each step in the mechanism. How might you use Le Châtelier s principle to favor products? How might you use Le Châtelier s principle to favor reactants? Is there an entropy difference that might be exploited? Soap is made through the saponification of triglycerides. EXPLAIN HOW. Klein, Organic Chemistry 1e 21-24

25 21.12 Preparation and Reactions of Amides Nylon is a polyamide. Polyester is made similarly. HOW? Klein, Organic Chemistry 1e 21-25

26 Amides can be hydrolyzed with H 3 O +, but the process is slow and requires high temperature. The mechanism is very similar to that for the hydrolysis of an ester. Show a complete mechanism. WHY is the process generally slow? Klein, Organic Chemistry 1e 21-26

27 21.12 Preparation and Reactions of Amides LAH can reduce an amide to an amine. The mechanism is quite different from the others we have seen in this chapter. When the H - attacks, which is the best leaving group? Klein, Organic Chemistry 1e 21-27

28 21.8 Preparation and Reaction of Acid Chlorides Klein, Organic Chemistry 1e 21-28

29 21.9 Preparation and Reactions of Acid Anhydrides Klein, Organic Chemistry 1e 21-29

30 1. No errors 2. 1 error 3. 2 errors 4. 3 or more errors 5. Not sure 6. Need more time CYUQ 15?

31 21.14 Synthetic Strategies Klein, Organic Chemistry 1e 21-31

32 1. No errors 2. 1 error 3. 2 errors 4. 3 or more errors 5. Not sure 6. Need more time Pg 117

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