General, Organic & Biological Chemistry, 5e (Timberlake) Chapter 16 Carboxylic Acids and Esters 16.1 Multiple-Choice Questions 1) Which functional group is a carboxylic acid? A) - OH B) O - C - OH C) O -C-OD) OH | - C - OH | E) - CH2 - OH Answer: B Objective: 16.1 Global Outcomes: GO2 2) The functional group in acetic acid is called the A) hydroxyl group B) aldehyde group C) carbonyl group D) carboxyl group E) ester group Answer: D Objective: 16.1 Global Outcomes: GO2 3) Which of the following is found in vinegar? A) nitric acid B) formic acid C) acetic acid D) propionic acid E) butyric acid Answer: C Objective: 16.1 Global Outcomes: GO2 Copyright © 2016 Pearson Education, Inc 4) What is the common name of the compound? O CH3 - CH2 - CH2 - C - OH is A) acetic acid B) propanoic acid C) propionic acid D) butanoic acid E) butyric acid Answer: E Objective: 16.1 Global Outcomes: GO2 5) What is the IUPAC name of the following compound? A) propyl butanoate B) butanoic acid C) 1-butanal D) 1-butanoate E) propyl methanoate Answer: B Objective: 16.1 Global Outcomes: GO2 6) In the compound below, the hydroxyl group is in which position? O CH3 - CH2 - CH - C - OH | OH A) B) C) D) E) Answer: B Objective: 16.1 Global Outcomes: GO2 Copyright © 2016 Pearson Education, Inc 7) The compound below is named A) benzoic acid amine B) 3-aminobenzoic acid C) 2-acid aniline D) benzamide E) 2-aminobenzoic acid Answer: B Objective: 16.1 Global Outcomes: GO2 8) Which of these functional groups is likely to give a sour taste to a food? A) ester B) ether C) ketone D) carboxylic acid E) thiol Answer: D Objective: 16.1 Global Outcomes: GO2 9) What is the IUPAC name for this compound? CH3 O | CH3 - CH - CH2 - C - OH A) pentanoic acid B) γ-methylbutanoic acid C) 3-methylbutanoic acid D) γ-methyl butyric acid E) 2-methyl-4-butanoic acid Answer: C Objective: 16.1 Global Outcomes: GO2 Copyright © 2016 Pearson Education, Inc 10) What is the IUPAC name for this compound? CH3 O | CH3 - CH - CH2 - C - OH A) pentanoic acid B) 2-methylbutanoic acid C) 3-methylbutanoic acid D) 2-methyl butyric acid E) 2-methyl-4-butanoic acid Answer: C Objective: 16.1 Global Outcomes: GO2 11) What kind of taste carboxylic acids have? A) sweet B) sour C) fruity D) slippery E) oily Answer: B Objective: 16.1 Global Outcomes: GO7 12) W hat is the common name for ethanoic acid? A) butyric acid B) formic acid C) citric acid D) stearic acid E) acetic acid Answer: E Objective: 16.1 Global Outcomes: GO2 13) What is the irritating acid found in ant and bee stings? A) acetic acid B) formic acid C) citric acid D) butyric acid E) stearic acid Answer: B Objective: 16.1 Global Outcomes: GO7 Copyright © 2016 Pearson Education, Inc 14) Which organic acid accounts for the odor of rancid butter? A) propionic acid B) acetic acid C) formic acid D) butyric acid E) ethanoic acid Answer: D Objective: 16.1 Global Outcomes: GO7 15) In the common naming convention for carboxylic acids, what is the correct Greek letter used for the carbon adjacent to the carboxyl group? A) α B) β C) γ D) δ E) ε Answer: A Objective: 16.1 Global Outcomes: GO2 16) What therapeutic use is made of α-hydroxy acids? A) ulcer treatment B) fever reduction C) antibiotic D) reduction of skin pigmentation E) sunscreen Answer: D Objective: 16.1 Global Outcomes: GO7 17) What significant side effect is seen with α-hydroxy acid use? A) UV sensitivity B) increased thirst C) nausea D) increased susceptibility to infection E) gastric irritation Answer: A Objective: 16.1 Global Outcomes: GO7 Copyright © 2016 Pearson Education, Inc 18) What α-hydroxy acid is found predominantly in grapes? A) tartaric acid B) citric acid C) lactic acid D) glycolic acid E) benzoic acid Answer: A Objective: 16.1 Global Outcomes: GO2 19) What is the method of preparing carboxylic acids from alcohols or aldehydes? A) reduction B) hydration C) oxidation D) saponification E) hydrolysis Answer: C Objective: 16.1 Global Outcomes: GO2 20) A carboxylic acid is prepared from an aldehyde by A) oxidation B) reduction C) hydrolysis D) neutralization E) hydrogenation Answer: A Objective: 16.1 Global Outcomes: GO2 Copyright © 2016 Pearson Education, Inc 21) The structural formula of the carboxylic acid produced by the oxidation of 2,2-dimethyl-1-propanol is A) CH3 O | CH3 C - CH | CH3 B) CH3 O CH3 | | CH3 C - C - O C CH3 | | CH3 CH3 C) O CH3CH2CH2CH2 C OH D) CH3 O | CH3 C - C OH | CH3 E) CH3 | CH3 C - OH | CH3 Answer: D Objective: 16.1 Global Outcomes: GO2 22) A carboxylic acid is named in the IUPAC system by replacing the -e in the name of the parent alkane with A) -oic acid B) -oic C) -carboxylic acid D) acid E) -oate Answer: A Objective: 16.1 Global Outcomes: GO2 Copyright © 2016 Pearson Education, Inc 23) Which carboxylic acid in the list below is an aromatic carboxylic acid? A) acetic acid B) benzoic acid C) butyric acid D) benzene E) citric acid Answer: B Objective: 16.1 Global Outcomes: GO2 24) What kind of intermolecular bonding occurs between carboxylic acids? A) ionic bonding B) nonpolar bonding C) covalent bonding D) hydrogen bonding E) charge-transfer bonding Answer: D Objective: 16.1 Global Outcomes: GO2 25) Why carboxylic acids have higher boiling points than similar alcohols or aldehydes? A) They form dimers that are relatively stable B) They are more water soluble C) They have higher molecular weights D) They have an additional oxygen atom E) The carboxylic acid chain is not linear Answer: A Objective: 16.2 Global Outcomes: GO2 26) What happens to water solubility as chain length increases in carboxylic acids? A) It increases B) It decreases C) It stays the same Answer: B Objective: 16.2 Global Outcomes: GO2 27) What is the common use of monosodium glutamate? A) as a preservative B) as a disinfectant C) as an anti-pyretic D) as a flavor enhancer E) as a spoilage inhibitor Answer: D Objective: 16.2 Global Outcomes: GO2 Copyright © 2016 Pearson Education, Inc 28) What common use is made of sodium propionate and sodium benzoate? A) flavor enhancer B) preservative C) pH adjuster D) disinfectant E) decongestant Answer: B Objective: 16.2 Global Outcomes: GO7 29) What metabolic product of pyruvic acid is formed anaerobically during exercise? A) lactic acid B) citric acid C) malic acid D) acetic acid E) β-ketoglutaric acid Answer: A Objective: 16.2 Global Outcomes: GO7 30) Which of these is an acid formed in the citric acid cycle? A) acetic acid B) propionic acid C) α-ketoglutaric acid D) benzoic acid E) palmitic acid Answer: C Objective: 16.2 Global Outcomes: GO7 31) When compared to sulfuric acid, how strong are carboxylic acids? A) stronger B) just as strong C) weaker D) not acidic at all Answer: C Objective: 16.2 Global Outcomes: GO2 32) In water solution, how does dilute acetic acid behave? A) as a strong acid B) as a weak acid C) as a strong base D) as a weak base E) as a neutral compound Answer: B Objective: 16.2 Global Outcomes: GO2 Copyright © 2016 Pearson Education, Inc 33) Which of the following is the reaction for the ionization of β-hydroxypropanoic acid in water? A) O OH | HO - CH2 - CH2 - C - OH + H2O B) HO - CH2 - CH2 - CH - OH + H+ ↔ O O HO - CH2 - CH2 - C - OH + H2O C) HO - CH2 - CH2 - C - O- + H3O+ ↔ O O CH3 - CH - C - OH + H2O ↔ CH3 - CH - C - O- + H3O+ | | OH OH D) O O HO - CH2 - CH2 - C - OH + H2O E) O ↔ -OCH CH C O- + H O+ 2 O CH3 CH C OH + H2O↔ CH3 - CH - C - OH + H3O+ | | OH OAnswer: B Objective: 16.2 Global Outcomes: GO2 34) The neutralization of formic acid by NaOH produces A) sodium formate as the only product B) formate ion and hydronium ion C) sodium formaldehyde D) methyl alcohol E) sodium formate and H2O Answer: E Objective: 16.2 Global Outcomes: GO2 10 Copyright © 2016 Pearson Education, Inc 35) Which of the following compounds is most soluble in water? A) CH3 - CH2 - CH3 B) CH3 - CH2 - CH2 - O - CH3 C) CH3 - CH2 - CH2 - CH2 - OH D) O CH3 - CH2 - CH2 - CH2 - C - OH E) O CH3 - C - OH Answer: E Objective: 16.2 Global Outcomes: GO2 36) Which of the following is the reaction for the neutralization of β-hydroxybutyric acid with NaOH? A) OH O OH O | | CH3 - CH - CH2 - C- OH + NaOH → CH3 - CH - CH2 - C - O- Na+ + H2O B) OH O OH O | | CH3 - CH - CH2 - C- OH + NaOH → CH3 - C - CH2 - C - OH + NaH | OH C) OH O OH | CH3 - CH2 - CH - C- OH + NaOH D) OH O | O → CH3 - CH2 - CH - C - O- Na+ + H2O O- Na+ O | | CH3 - CH - CH2 - C- OH + NaOH→ CH3 - CH - CH2 - C - O- Na+ + H2O E) O O CH3 - CH2 - CH - C- OH + NaOH→ CH3 - CH2 - CH - C - O- Na+ + H2O | | OH OH Answer: A Objective: 16.2 Global Outcomes: GO2 37) Which compound below contains an ester functional group? A) OH | CH3 - CH - CH2 - CH3 11 Copyright © 2016 Pearson Education, Inc B) CH3 - CH2 - O - CH2- CH3 C) O H - C - O - CH2- CH3 D) O CH3 - C - CH2 - CH3 E) O CH3 - C - OH Answer: C Objective: 16.3 Global Outcomes: GO2 38) What is the product of the reaction of pentanoic acid with ethanol in the presence of a strong acid? A) pentyl ethanoate B) ethyl pentanoate C) pentyl acetate D) heptanoic acid Answer: B Objective: 16.3 Global Outcomes: GO2 39) This functional group is known as a(n) O -C-O-C A) ester B) carboxylic acid C) alcohol D) aldehyde E) acetal Answer: A Objective: 16.3 Global Outcomes: GO2 12 Copyright © 2016 Pearson Education, Inc 40) The reactants that will form an ester in the presence of an acid catalyst are A) two carboxylic acids B) two alcohols C) a carboxylic acid and an alcohol D) an aldehyde and an alcohol E) two aldehydes Answer: C Objective: 16.3 Global Outcomes: GO2 41) Which of these compounds is the ester formed from the reaction of acetic acid and 1propanol? A) O CH3 - CH2 - C - O - CH2- CH3 B) OH | CH3 - C - OH | O - CH2 - CH2 - CH3 C) OH | CH3 - CH2 - C - OH | O - CH2 - CH3 D) O CH3 - C - O - CH2 - CH2 - CH3 E) O CH3 - CH2 - CH2 - O - CH2- C - OH Answer: D Objective: 16.3 Global Outcomes: GO2 42) The alcohol and carboxylic acid required to form propyl ethanoate are A) methanol and propionic acid B) ethanol and propionic acid C) propanol and propanoic acid D) 1-propanol and ethanoic acid E) 2-propanol and ethanoic acid Answer: D Objective: 16.3 Global Outcomes: GO2 43) What is the product of the reaction of an alcohol and a carboxylic acid when reacted together under acidic conditions? A) an ether B) an ester C) a salt 13 Copyright © 2016 Pearson Education, Inc D) a ketone E) an aldehyde Answer: B Objective: 16.3 Global Outcomes: GO2 44) Derivatives of which aromatic carboxylic acid have been used as analgesics, antipyretics, and anti-inflammatory agents? A) benzoic acid B) anthranilic acid C) naphthenic acid D) p-toluenesulfonic acid E) salicylic acid Answer: E Objective: 16.3 Global Outcomes: GO7 45) Many of the fragrances of flowers and the flavors of fruits are due to A) ethers B) carboxylic acids C) esters D) amines E) amides Answer: C Objective: 16.3 Global Outcomes: GO7 46) What is the common name of this compound? O CH3 - C - O - CH2 - CH3 A) ethyl methyl ester B) diethyl ester C) ethyl methanoate D) 2-ether-2-butanone E) ethyl acetate Answer: E Objective: 16.4 Global Outcomes: GO2 14 Copyright © 2016 Pearson Education, Inc 47) Give the IUPAC name for the following compound A) ethyl propyl ether B) ethyl propanoate C) ethyl butanoate D) hexanoic acid E) 4-hexanal Answer: C Objective: 16.4 Global Outcomes: GO2 48) Give the IUPAC name for the following compound A) methyl formyl ether B) methyl methanoate C) methyl ethanoate D) methyl formate E) ethanoate Answer: B Objective: 16.4 Global Outcomes: GO2 49) From what component is the first part of the IUPAC name of an ester (such as methyl acetate) derived? A) the carboxylic acid B) the alcohol C) the ether D) the ester E) the amide Answer: B Objective: 16.4 Global Outcomes: GO2 15 Copyright © 2016 Pearson Education, Inc 50) The splitting apart of an ester in the presence of a strong acid and water is called A) hydrolysis B) saponification C) neutralization D) esterification E) reduction Answer: A Objective: 16.5 Global Outcomes: GO2 51) Which of the following is the reaction for the acid hydrolysis of ethyl formate? A) O O CH3 - C - O- Na+ + CH3 - OH CH3 - C - O - CH3 + NaOH→ B) O O CH3 - C - O - CH3 + H2O → CH3 - C - OH + CH3 - OH C) O O H - C - O - CH3 + H2O → H - C - OH + CH3 - OH D) O H - C - O - CH2 - CH3 + H2O E) O H - C - O - CH2 - CH3 + H2O O → H - C - OH + CH3 - CH2 - OH OH | → H - C - O - CH2 - CH3 | Answer: D OH Objective: 16.5 Global Outcomes: GO2 16 Copyright © 2016 Pearson Education, Inc 52) Which of the following is the reaction for the saponification of methyl acetate? A) O O CH3 - C - O - CH3 + NaOH→ B) CH3 - C - OH + CH3 - O- Na+ O CH3 - C - O - CH3 + NaOH→ C) O O CH3 - C - O- Na+ + CH3 - OH O H - C - O - CH3 + H2O → H - C - O- + CH3 - OH D) O O H - C - O - CH3 + NaOH → E) O CH3 - C - O - CH3 + H2O → H - C - O- Na+ + CH3 - OH O CH3 - C - O- + CH3 - OH Answer: B Objective: 16.5 Global Outcomes: GO2 53) The reaction of an ester with NaOH is known as A) esterification B) neutralization C) saponification D) reduction E) oxidation Answer: C Objective: 16.5 Global Outcomes: GO2 54) What chemical process is responsible for the smell of vinegar in an old bottle of aspirin? A) reduction B) hydration C) hydrolysis D) esterification E) dissolution Answer: C Objective: 16.5 Global Outcomes: GO2 55) Which part of a soap is responsible for its ability to dissolve fats and oily dirt? A) the hydrophilic end B) the hydrophobic end C) the carboxylate D) the ionized oxygen 17 Copyright © 2016 Pearson Education, Inc E) the carbonyl group Answer: B Objective: 16.5 Global Outcomes: GO2 56) What is the name of the structure formed when a soap coats an oily particle to make it water soluble? A) micelle B) cluster C) liposome D) dimer E) lipid Answer: A Objective: 16.5 Global Outcomes: GO2 16.2 True-False Questions 1) Carboxylic acids are responsible for the sweet taste of fruits and vegetables Answer: FALSE Objective: 16.1 Global Outcomes: GO7 2) The major acidic component of vinegar is formic acid Answer: FALSE Objective: 16.1 Global Outcomes: GO7 3) Alpha-hydroxy acids should be used at concentrations under 10% in skin care products Answer: TRUE Objective: 16.1 Global Outcomes: GO7 4) It is always safe to use any commercial skin care product without doing a test patch first Answer: FALSE Objective: 16.1 Global Outcomes: GO7 5) Benzoic acid is an aromatic carboxylic acid Answer: TRUE Objective: 16.1 Global Outcomes: GO2 18 Copyright © 2016 Pearson Education, Inc 6) The IUPAC name of this compound is propanoic acid Answer: FALSE Objective: 16.1 Global Outcomes: GO2 7) Carboxylic acids with more than five carbons are very water soluble Answer: FALSE Objective: 16.2 Global Outcomes: GO2 8) The boiling points of carboxylic acids are lower than the corresponding alcohols Answer: FALSE Objective: 16.2 Global Outcomes: GO2 9) Carboxylic acids with four or fewer carbons are very water soluble Answer: TRUE Objective: 16.2 Global Outcomes: GO2 10) Sodium propionate is a common disinfectant Answer: FALSE Objective: 16.2 Global Outcomes: GO7 11) When in solution, carboxylic acids are mostly in their ionized forms Answer: FALSE Objective: 16.2 Global Outcomes: GO2 12) Sodium benzoate is a common preservative Answer: TRUE Objective: 16.2 Global Outcomes: GO6 13) Citric acid is an important part of glycolysis Answer: FALSE Objective: 16.2 Global Outcomes: GO6 14) The Krebs cycle is a process that the cell uses to produce energy Answer: TRUE Objective: 16.2 Global Outcomes: GO6 19 Copyright © 2016 Pearson Education, Inc 15) The Krebs cycle and the citric acid cycle are different processes Answer: FALSE Objective: 16.2 Global Outcomes: GO6 16) Carboxylic acids are strong acids Answer: FALSE Objective: 16.2 Global Outcomes: GO2 17) When benzoic acid is neutralized by sodium hydroxide, sodium benzoate is formed Answer: TRUE Objective: 16.2 Global Outcomes: GO2 18) Esters are formed from the reaction of an ether with a carboxylic acid Answer: FALSE Objective: 16.3 Global Outcomes: GO2 19) An ester is derived from an alcohol and a carboxylic acid Answer: TRUE Objective: 16.3 Global Outcomes: GO2 20) Methyl salicylate (oil of wintergreen) is used therapeutically as a counter-irritant Answer: TRUE Objective: 16.3 Global Outcomes: GO7 21) Polyesters are plastics that are used to make fabrics, bottles, and medical devices such as heart valves Answer: TRUE Objective: 16.3 Global Outcomes: GO7 22) Butyl alcohol is one of the reactants used to make methyl butyrate Answer: FALSE Objective: 16.3 Global Outcomes: GO2 23) The ester formed from butyl alcohol and acetic acid is called butyl acetate Answer: TRUE Objective: 16.4 Global Outcomes: GO2 20 Copyright © 2016 Pearson Education, Inc 24) The IUPAC name of this compound is methyl butanoate Answer: TRUE Objective: 16.4 Global Outcomes: GO2 25) Long chain carboxylic acids are also known as fatty acids Answer: TRUE Objective: 16.5 Global Outcomes: GO2 26) Aspirin that has a smell of vinegar has broken down by hydrolysis Answer: TRUE Objective: 16.5 Global Outcomes: GO2 27) Soaps are salts of long chain fatty acids Answer: TRUE Objective: 16.5 Global Outcomes: GO2 21 Copyright © 2016 Pearson Education, Inc 16.3 Matching Questions Identify the family for each of the following compounds A) ketone B) carboxylic acid C) ester 1) O CH3 - C - CH3 Objective: 16.1, 16.3 Global Outcomes: GO2 2) O CH3 - CH2 - C - OH Objective: 16.1, 16.3 Global Outcomes: GO2 3) O CH3 - CH2 - C - O - CH3 Objective: 16.1, 16.3 Global Outcomes: GO2 Answers: 1) A 2) B 3) C 22 Copyright © 2016 Pearson Education, Inc Select the correct name for the following A) ethyl formate B) sodium formate C) formic acid 4) O H - C - OH Objective: 16.1, 16.4 Global Outcomes: GO2 5) O H - C - O - CH2 - CH3 Objective: 16.1, 16.4 Global Outcomes: GO2 6) O H - C - O- Na+ Objective: 16.1, 16.4 Global Outcomes: GO2 Answers: 4) C 5) A 6) B 23 Copyright © 2016 Pearson Education, Inc ... CH3 - C - CH3 Objective: 16. 1, 16. 3 Global Outcomes: GO2 2) O CH3 - CH2 - C - OH Objective: 16. 1, 16. 3 Global Outcomes: GO2 3) O CH3 - CH2 - C - O - CH3 Objective: 16. 1, 16. 3 Global Outcomes: GO2... Objective: 16. 3 Global Outcomes: GO2 42) The alcohol and carboxylic acid required to form propyl ethanoate are A) methanol and propionic acid B) ethanol and propionic acid C) propanol and propanoic... - O - CH2 - CH3 Objective: 16. 1, 16. 4 Global Outcomes: GO2 6) O H - C - O- Na+ Objective: 16. 1, 16. 4 Global Outcomes: GO2 Answers: 4) C 5) A 6) B 23 Copyright © 2 016 Pearson Education, Inc