CARBOXYLIC ACIDS AND ESTERS

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1 C24 09/17/ :59:46 Page 350 CHAPTER 24 CARBXYLIC ACIDS AND ESTERS SLUTINS T REVIEW QUESTINS 1. (a) CH (d) (e) (f) (g) CH 2 CHCH (h) (i) CN (j) CNa (k) (l) (m) (CH 2 ) 16 CNa (n) H P H (o) H P H H 2. The butyric acid solution would be expected to have the more objectionable odor because salts normally exhibit little or no odor. Salts are ionic and therefore have low volatility. For example, dilute solutions of acetic acid (vinegar) have considerable odor, but sodium acetate does not. 3. Which has the greater solubility in water? (a) Propanoic acid is more soluble than methyl propanoate. Sodium palmitate is more soluble than palmitic acid. Sodium stearate is more soluble than barium stearate. (d) Sodium phenoxide is more soluble than phenol. 4. Unlike alkanes, carboxylic acids hydrogen bond tightly to each other. Thus, they have much higher boiling points than alkanes. 5. (a) The major difference between fats and oils is that fats are solids at room temperature, oils are liquids. The fatty acids in the molecules are mostly saturated in fats; more unsaturated in oils

2 C24 09/17/ :59:46 Page 351 Soaps are the sodium salts of high molar mass fatty acids. Syndets are synthetic detergents and occur in several different forms. They have cleansing action similar to soaps, but have different structural and solubility characteristics, such as being soluble in hard water. Some syndets also contain long hydrocarbon chains. Hydrolysis is the breaking apart of an ester in the presence of water to form an alcohol and a carboxylic acid. Mineral acids or digestive enzymes are used to speed the hydrolysis process. Saponification breaks the ester apart using sodium hydroxide to form an alcohol and a salt of a carboxylic acid. 6. A sour taste is associated with acids. Citrus fruits and rhubarb are examples of foods that have a sour, acid taste. 7. Like a soap, a detergent contains a grease-soluble component and a water-soluble component. The grease-soluble component of many molecules dissolves in the grease film. The watersoluble components attract water, causing small droplets of grease-bearing dirt to break loose and float away. 8. The principal advantage of synthetic detergents over soap is that the syndets do not form insoluble precipitates with the ions in hard water (Ca 2þ,Mg 2þ,Fe 3þ ). 9. Aspirin acts in the body as an antipyretic, an analgesic, and as an antiinflammatory agent. 10. In a condensation reaction one of the products formed is a small molecule such as water. In polyester formation between an alcohol and a carboxylic acid, water is formed in addition to the ester (polyester). 11. Polyesters are polymers of molecules linked together by ester bonds. The ester bonds are susceptible to hydrolysis (being broken by reaction with water). When a polyester suture dissolves, the polymer s ester bonds are broken. 12. (a) Phosphoric acid anhydrides are used by living cells to store metabolic energy. The energy currency of the cell is adenosine triphosphate (ATP) that contains two phosphoric acid anhydrides. The phosphoric acid ester (or phosphate ester) has many important biochemical functions. ften a phosphate ester is used to tag a biochemical, labeling it for specific biological uses. 13. Partial hydrogenation of oils is no longer commonly used by the food industry because this process produces some trans fats. These fats are known to increase the risk of atherosclerosis. 14. MSG stands for monosodium glutamate. It is the sodium salt of the common amino acid, glutamic acid. The sodium salt is formed in an acid-base reaction between glutamate and a base such as sodium hydroxide. 15. Both compounds have a hydrophilic structural component. Capric acid contains a nine-carbon hydrocarbon chain which decreases its solubility in water. Formic acid does not have a hydrocarbon chain

3 C24 09/17/ :59:46 Page An ester is formed by bonding an hydroxyl group (alcohol) to an acid with the release of water. This compound meets the definition of ester because it combines phosphoric acid with ethanol. H P CH 2 H from phosphoric acid from ethanol 17. Hard water contains much higher concentrations of Ca 2þ,Mg 2þ, and Fe 3þ ions than soft water. Soaps precipitate (forming a soap scum) with these ions while synthetic detergents do not

4 C24 09/17/ :59:46 Page 353 SLUTINS T EXERCISES 1. (a) lactic acid phthalic acid (o-phthalic acid) succinic acid (d) propionic acid 2. (a) m-toluic acid butyric acid b-chloropropionic acid (d) glutaric acid 3. (a) 2,3-dichloropropanoic acid 2-methylbutanoic acid hexanoic acid (d) propanedioic acid 4. (a) propanoic acid butanedioic acid 2,4-dimethylpentanoic acid (d) 2-hydroxybutanoic acid H 5. (a) CHCH 2 CH (d) (e) CH 2 CH 2 CH 2 CH CH 2 C K þ CH C Na þ (f) CH 2 CH 2 CCH 2 CH (g) CH 6. (a) HCCH 2 CH H CH 2 CH 2 CHCH 2 CHCH Cl CH3CHCH - + (d) C Na

5 C24 09/17/ :59:47 Page 354 (e) HC CH (f) (g) CH 2 CH CH 2 CH 2 C Li þ 7. (a) Acetic acid is a common name. The IUPAC name is ethanoic acid. 2-Bromo-1-hexanoic acid is incorrect because the carboxyl functional group should not be numbered. The correct IUPAC name is 2-bromohexanoic acid. In a-chloropropanoic acid, the Greek letter is common nomenclature. The correct IUPAC name is 2-chloropropanoic acid. 8. (a) In b-bromobutanoic acid, the Greek letter is common nomenclature. The correct IUPAC name is 3-bromobutanoic acid. Lactic acid is a common name. The IUPAC name is 2-hydroxypropanoic acid. 3-Ethyl-5-pentanoic acid incorrectly includes a number for the carboxyl functional group. The correct IUPAC name is 3-ethylpentanoic acid. 9. Increasing ph means increasing basicity HCl H < CH < < NaCl < NH3 < NaH Increasing ph 10. Decreasing ph means increasing acidity KH H > NH 3 > KBr > > HCH > HBr Decreasing ph 11. (a) succinic acid acetic acid butanoic acid (d) butanoic acid 12. (a) ethanoic acid ethanoic acid propanoic acid (d) malonic acid 13. IUPAC and common names (a) methyl propenoate ethyl butanoate phenyl-2-hydroxybenzoate 14. IUPAC and common names (a) methyl methanoate propyl benzoate ethyl propanoate methyl acrylate ethyl butyrate phenyl salicylate methyl formate propyl benzoate ethyl propionate

6 C24 09/17/ :59:47 Page Structural formulas (a) 16. Structural formulas (a) 17. (a) Compounds are different: methyl propanoate and ethyl ethanoate Compounds are the same Compounds are different: methyl 2-methylpropanoate and isopropyl ethanoate 18. (a) Compounds are different: methyl benzoate and phenyl acetate Compounds are different: methyl acetate and methyl propanoate Compounds are the same 19. Structural formula for the ester that when hydrolyzed would yield: (a)

7 C24 09/17/ :59:47 Page Structural formula for the ester that when hydrolyzed would yield: (a) 21. Structural formulas for the reactants that will yield the following esters: (a) 22. Structural formulas for the reactants that will yield the following esters: (a) 23. (a) These reagents (Na 2 Cr 2 7,H 2 S 4 ) oxidize the aldehyde to a carboxylic acid. H 3 C C CH 2 CH 3,3-dimethylbutanoic acid

8 C24 09/17/ :59:47 Page 357 These reagents (Na 2 Mn 4, NaH, D) oxidize the alkyl side chain to form the salt of benzoic acid. C Na sodium benzoate This is an acid-base reaction that forms the salt of the carboxylic acid. CH 2 CH 2 C K þ potassium butanoate 24. (a) These reagents (Na 2 Mn 4, NaH, D) oxidize the alkyl side chain to form the salt of benzoic acid. C Na sodium benzoate These reagents (Na 2 Cr 2 7,H 2 S 4 ) oxidize the primary alcohol to a carboxylic acid. CH 2 CH 2 CH butanoic acid This is an acid-base reaction that forms the salt of the carboxylic acid. CH 2 C Na þ sodium propanoate 25. (a) A carboxylic acid reacts with a carboxylic acid chloride to yield a carboxylic acid anhydride. CH 2 CH 2 C C C H 3 A nitrile reacts with water to form a carboxylic acid. CH A carboxylic acid chloride reacts with an alcohol to form an ester. CH 2 C CH (a) A nitrile reacts with water to form a carboxylic acid. CH 2 CH

9 C24 09/17/ :59:47 Page 358 A carboxylic acid chloride reacts with an alcohol to form an ester. C CH 2 CH 2 A carboxylic acid reacts with an alcohol to form an ester. H C CH Simple test to distinguish between: (a) Sodium benzoate and benzoic acid: Sodium benzoate is water soluble; benzoic acid is not. Maleic acid and malonic acid. Maleic acid has a carbon-carbon double bond, it will readily add and decolorize bromine; malonic acid will not decolorize bromine. 28. Simple tests to distinguish between: (a) Benzoic acid and ethyl benzoate; benzoic acid is an odorless solid; ethyl benzoate is a fragrant liquid. Succinic acid and fumaric acid: fumaric acid has a carbon-carbon double bond and will readily add and decolorize bromine; succinic acid will not decolorize bromine. 29. (a) CH 2 CH + NaH CH 2 C Na þ + H 2 CH 2 CH + H 99: CH 2 C + H (a) CHCH 2 CH + SCl 2 99: CHCH 2 CCl + S 2 + HCl CHCH 2 CH + CH3CH2CH2H 99: CH3CHCH2CCH2CH2CH3 + H (a) These reagents (NaH, H 2, D) cause saponification of the ester. H þ CH 2 C Na þ These reagents (H þ,h 2 ) cause hydrolysis of the ester. CH 2 H þ CH 32. (a) These reagents (H þ,h 2 ) cause hydrolysis of the ester. H CH + CH3CH 2 CH

10 C24 09/17/ :59:48 Page 359 These reagents (NaH, H 2, D) cause saponification of the ester. H þ CH 2 CH 2 CH 2 CH 2 C Na þ 33. (a) CH 2 CH 2 C HCl + H 2 CH 2 CH 2 CH + H H HCCH 2 + NaH 2 99: Δ HC Na + + CH 2 H 34. (a) CH 2 CCH 2 H 2 + KH CH 2 C K + Δ + CH 2 H CH 2 CH 2 CCH 2 CH 2 HCl + H 2 CH 2 CH 2 CH + CH 2 CH 2 H 35. (a) These reagents (H 2, H þ ) cause hydrolysis of the diacylglycerol. CH 2 H CHH + 2 (CH 2 ) 10 CH CH 2 H These reagents (H 2, Ni) reduce the double bond. ðch 2 Þ 14 CH These reagents (H 2, copper chromite, D, pressure) cause hydrogenolysis of the triacylglycerol. CH 2 H CHH + 3 (CH 2 ) 12 CH 2 H CH 2 H 36. (a) These reagents (H 2, Ni) reduce the double bond. ðch 2 Þ 16 CH These reagents (H 2, copper chromite, D, pressure) cause hydrogenolysis of the triacylglycerol. CH 2 H CHH + 3 (CH 2 ) 10 CH 2 H CH 2 H

11 C24 09/17/ :59:48 Page 360 These reagents (H 2, H þ ) cause hydrolysis of the triacylglycerol. CH 2 H CHH + 3 (CH 2 ) 14 CH CH 2 H 37. H 2 C HC C(CH 2 ) 12 C(CH 2 ) H 2 H + H 2 C HC H H + 3 (CH 2 ) 12 CH H 2 C C(CH 2 ) 12 H 2 C H 38. H 2 C C(CH 2 ) 14 H 2 C H HC C(CH 2 ) H 2 copper chromite Δ, pressure HC H + 3 (CH 2 ) 14 CH 2 H H 2 C C(CH 2 ) 14 H 2 C H 39. (CH 2 ) 12 CNa would be more useful than (CH 2 ) 12 CH as a cleansing agent in soft water. Both have a long hydrocarbon chain which would dissolve in the fat, but the acid is not water soluble, whereas the sodium salt is soluble in water. 40. Sodium lauryl sulfate would be more effective as a detergent in hard water than sodium propyl sulfate because the hydrocarbon chain is only three carbons long in the latter, not long enough to dissolve grease well. Sodium lauryl sulfate is effective in both hard and soft water. 41. nly (a), hexadecyltrimethyl ammonium chloride would be a good detergent in water. It is cationic. 42. nly (CH 2 ) 10 CH 2 (CH 2 CH 2 ) 7 CH 2 CH 2 H, would be a good detergent in water. It is nonionic. 43. (a) H P H + H H+ HCH 2 99: H P CH 2 + H 2 H

12 C24 09/17/ :59:48 Page 361 H P H CH 2 + CH 2 CH 2 H H + 99: H P CH 2 + H 2 CH 2 CH (a) H P H H + 3 H H + 99: P + 3 H 2 H P H + H H + 99: P H P H + CH 2 CH H H H + H 2 H H+ 99: P CHCH 2 H 45. Grams and moles of sodium benzoate (NaC 7 H 5 2 ): 0:001 1lb 454 g 1lb ¼ 0:5 g sodium benzoate 0:5 g NaC 7 H mol 145:1g ¼ mol NaC 7 H 5 2 CH CH H C 46. ± C C ± CH salicylic acid acetic anhydride aspirin (acetylsalicylic acid) 47. The ester is propyl propanoate CH 2 CCH 2 CH 2 acetic acid Compound A is an acid; B is an alcohol. If B is oxidized to an acid which is the same as A, then A and B both have the same carbon structure, three carbon atoms each. The acid A must be propanoic acid, CH 2 CH. The alcohol can be 1-propanol or 2-propanol. nly 1-propanol can be oxidized to propanoic acid which is the same as compound A. 48. Phosgene (CCl 2 ) contains two acid chloride functional groups. When phosgene (acid chlorides) reacts with bisphenol A (alcohols), esters are formed

13 C24 09/17/ :59:48 Page Polyesters are polymers of molecules linked together by ester bonds. The ester bonds are susceptible to hydrolysis (being broken by reaction with water). When a polyester suture dissolves, the polymer s ester bonds are broken. 50. CH Ð C þ H þ 98:7% 1:3% f the total concentration of 0.1M, (0.013)(0.1M) is in the form of acetate. The acetate concentration is M. 51. (a) There are two phosphoric acid esters and no phosphoric acid anhydrides. There is one phosphoric acid ester and one phosphoric acid anhydride. 52. Complete hydrogenation will convert the carbon-carbon double bonds to single bonds

14 C24 09/17/ :59:48 Page There are two other triacylglycerols containing all three of these acids. Each of the three acids can be attached to the middle carbon of the glycerol. 54. Names and formulas of products are (a) (d) CH 2 C(CH 2 ) 10 CH C(CH 2 ) 14 CH 2 C(CH 2 ) 16 lauroylpalmitoylsteroylglycerol

15 C24 09/17/ :59:48 Page CH C A B C C 10 H 12 2 C 7 H 8 + C 3 H 6 2 A (has a B (alcohol) C (acid) benzene ring) CH 2 C CH 2 CH 2 H CH 2 CH A B C (1) C cannot be a benzene ring. If C is an acid, it must be propanoic acid. (2) If B is an alcohol and has a benzene ring, it must be benzyl alcohol. Putting B and C together gives the ester A. 58. Smell both samples. Butanoic acid has an unpleasant rancid odor; ethyl butanoate has a pleasant odor of pineapple. 59. Each molecule of triolein requires three molecules of H 2 (one for each double bond) (a) ð1:00 kg trioleinþ 103 g 1 mol triolein 3 mol H2 22:4 L kg 885:4 g triolein 1 mol triolein 1 mol H 2 ¼ 75:9LH 2 ð1:00 kg trioleinþ ¼ 1:01 kg tristearin 891:5 g tristearin 885:4 g triolein 60. The statement is false. When methyl propanoate is hydrolyzed, propanoic acid and methanol are formed. 61. Esters of formula C 5 H

16 C24 09/17/ :59:49 Page (a) Mass percent of oxygen in dacron. Mass of one unit of dacron ¼ g Mass of oxygen in one unit of dacron ¼ g 64:00 g 100 ¼ 33:30% 192:2g Molar mass of 105 units ð105 unitsþ 192:2g ¼ 2: g unit 63. An alkyd polyester would most likely be thermosetting because glycerol is trifunctional and would thus allow cross linking between chains in forming the ester polymer. 64. Synthesis of: (a) acetic acid K 2 Cr 2 7 CH 2 H! CH H 2 S 4 ethyl acetate b-hydroxybutyric acid 65. (a)

17 C24 09/17/ :59:49 Page H H2 S 4 HBr Br KCN CN H2 H + CH 67. This polymer is formed as acids react with alcohols. Each reaction forms an ester splitting out a water molecule in the process. Thus, this is a condensation reaction. CH 2 C CH C CH 2 C CH C n This polymer has been formed with alternating glycolic acid and lactic acid monomers. ther arrangements are possible

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