5. How many different carboxylic acids have the molecular formula C 5 H 10 O 2? A) 2 B) 3 C) 4 D) More than 4

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1 1. This compound is the product of the reaction of: (Woods) Ch-15 & CH 3 CH 2 COONa A) a carboxylic acid with an alcohol C) a carboxylic acid with NaOH B) an alcohol with a ketone D) an ester with HCl and water 2. To prepare this compound we could: A) oxidize a primary alcohol C) react a carboxylic acid with a secondary alcohol B) react a carboxylic acid with a primary alcohol D) oxidize a secondary alcohol 3. Consider the following structures: O I. CH 3 CH 2 COCH 2 CH 3 II. CH 3 CH 2 CH 2 CH 2 COOH III. CH 3 CH 2 OCH=CHCH 2 OH IV. CH 3 COOCH(CH 3 ) 2 A) I and III only are the same compound. B) II and III only are constitutional isomers. C) I and IV only are constitutional isomers. D) I, II, III, and IV are all different compounds that are constitutional isomers. 4. These compounds are: OH I. CH 3 CH 2 CHOCH 2 CH 3 II. CH 3 CH 2 CH 2 CH 2 COOH A) the same C) different compounds that are geometrical isomers B) different compounds that are constitutional isomers D) different compounds that are not isomers 5. How many different carboxylic acids have the molecular formula C 5 H 10 O 2? A) 2 B) 3 C) 4 D) More than 4 6. Which compound can form a carboxylic acid if the proper reagent and proper conditions are chosen? I. CH 3 CH 2 CHOHCH 3 II. (CH 3 ) 2 CHOH III. (CH 3 ) 3 COH A) I only B) II only C) III only D) None of the compounds oxidize to carboxylic acids. 7. Treatment of 1-hexanol with potassium permanganate will yield: A) only hexanal B) 1-hexanone C) 2-hexanone D) primarily hexanoic acid 8. Treatment of 3-pentanol with potassium dichromate will yield: A) only pentanal B) 3-pentanone C) 2-pentanone D) primarily pentanoic acid 9. Treatment of hexanal with potassium permanganate will yield: A) primarily hexanol B) 1-hexanone C) 2-hexanone D) primarily hexanoic acid 10. The IUPAC name of this compound is: (CH 3 ) 2 CHCH 2 COOH A) isobutylcarboxylic acid B) 3-methylbutanoic acid C) isobutanoic acid D) 3-methylpentanoic acid 11. The IUPAC name of this compound is: (CH 3 ) 3 CCH 2 COOH A) isobutylcarboxylic acid B) isopentanoic acid C) 3,3-dimethylbutanoic acid D) 2,2-dimethylbutanoic acid

2 (Woods) Ch-15 & The IUPAC name of this compound is: (CH 3 ) 2 CHCH 2 COOCH 3 A) isobutyl methyl ether C) methyl-3-methylbutanoic acid B) methyl isobutanoic ester D) methyl-3-methylbutanoate 13. Arrange these compounds in order of increasing boiling point. I. 1-butanol II. butanal III. propanoic acid A) I < II < III B) II < I < III C) III < I < II D) II < III < I 14. Arrange these compounds in order of increasing boiling point. I. CH 3 CH 2 CH 2 COOH II. CH 3 CH 2 COOCH 3 III. (CH 3 ) 2 CHCH 2 CH 2 OH A) I < II < III B) I < III < II C) II < III < I D) III < I < II 15. An unknown compound may be: I. 1-propanol II. propanoic acid III. propanal The unknown does not turn blue litmus paper red. Which statement is true? B) The unknown must be II. D) The unknown could be I or III, but not II. 16. Arrange these compounds in order of increasing melting point. I. sodium propanoate II. propanoic acid III. 2-methyl-1-butanol A) I < II < III B) II < III < I C) I < III < II D) III < II < I 17. Arrange these compounds in order of increasing solubility in water. I. sodium propanoate II. propanoic acid III. 2-methyl-1-butanol A) I < III < II B) II < III < I C) I < II < III D) III < II < I 18. An unknown compound may be: I. phenol II. potassium propanoate III. pentanal The unknown turns blue litmus paper red. Which statement is true? B) The unknown must be II. D) The unknown could be I or II, but not III. 19. An unknown compound may be: I. potassium ethanoate II. butanol III. butanoic acid The unknown does not turn blue litmus paper red. Which statement is true? B) The unknown must be II. D) The unknown could be I or II, but not III. 20. Which compound is a soap? A) CH 3 (CH 2 ) 2 COONa B) CH 3 (CH 2 ) 2 COOH C) CH 3 (CH 2 ) 14 COONa D) CH 3 (CH 2 ) 14 COOH 21. Which compounds react together to form an ester? I. aldehyde II. ketone III. phenol IV. alcohol A) I and II only B) I and III only C) III and IV only D) No combination of these compounds will react to form an ester. 22. Which compounds react together to form an ester? I. CH 3 CH 2 OH II. CH 3 CH 2 CHO III. CH 3 CH 2 COOH IV. CH 3 CH 2 COCH 3 A) I and IV only B) II and III only C) I and III only D) Both I and II and I and IV would produce esters.

3 23. Which compounds react together to form an ester? I. (CH 3 ) 3 CCH 2 OH II. CH 3 CH 2 COOH III. CH 3 CH 2 CH 2 OH IV. CH 3 CH 2 COCH 3 A) I and II only B) I and IV only C) II and III only D) There are two possible combinations: I and II, and II and III. (Woods) Ch-15 & Name the carboxylic acid and the alcohol that react to produce this compound. (CH 3 ) 3 CCH 2 COOCH(CH 3 ) 2 A) t-butyl acid and isopropyl alcohol C) 3,3-dimethylbutanoic acid and 2-propanol B) isopropyl acid and t-butyl alcohol D) 2-propanoic acid and 3,3-dimethylbutanol 25. What is the IUPAC name of this compound? (CH 3 ) 2 CHCH 2 COO(CH 2 ) 5 CH 3 A) hexyl-3-methylbutanoate B) hexyl-4-methylpentanoate C) hexyl-isobutyl ester D) hexylisobutyric acid 26. What is the IUPAC name of this compound? CH 3 CH 3 CH 2 CHCOOCH 2 CH(CH 3 ) 2 A) 2-methylpropyl 3-methylbutanoate C) isobutyl isopentanoate B) 2-methylpropyl 2-methylbutanoate D) isobutyl s-pentyl ester 27. What are the products of the acid hydrolysis of s-butyl benzoate? A) butanoic acid and phenol C) 2-butanol and phenolic acid B) s-butyl alcohol and benzoic acid D) 3-butanol and benzoic acid 28. What is the IUPAC name of this compound? O O C 6 H 5 -C-O-C-C 6 H 5 A) benzylic anhydride B) benzoic anhydride C) benzoic ether D) benzoic ester 29. An unknown compound is either an ester or a carboxylic acid. Which simple chemical diagnostic test can be used to identify the functional group? A) Use Tollen's reagent to form a silver mirror with the ester. B) Add a drop of a solution of bromine dissolved in carbon tetrachloride to the unknown. The color will disappear if the unknown is an acid. C) Add NaOH solution. A reaction will occur with an ester, but not with a carboxylic acid. D) Add a drop of the unknown to blue litmus paper. The unknown is the carboxylic acid if the litmus paper changes color to red. 30. Saponification is the name for the: A) neutralization of an acid with NaHCO 3. C) hydrolysis of an acid anhydride. B) hydrolysis of an acetal. D) basic hydrolysis of an ester. 31. Arrange these one carbon compounds in order of decreasing oxidation number. I HCOOH II HCHO III CH 3 OH IV CO 2 A) III > II > I > IV B) IV > II > III > I C) IV > I > II > III D) I > II > III > IV 32. Which compound is paired with the correct oxidation number of its carbon atom? A) CH 4 (O.N. of C = +4) B) HCOOH (O.N. of C = +2) C) CH 3 OH (O.N. of C = -1) D) HCHO (O.N. of C = +1)

4 33. What are the names of these compounds? I. NH 2 CH 2 CH 2 CH 2 CH 2 NH 2 II. (CH 3 ) 2 CHN(CH 3 ) 2 A) I is 1,5-pentanediamine, and II is tetramethylamine. B) I is 1,4-butanediamine, and II is isopropylmethyamine. C) I is 1,4-butanediamine, and II is isopropyldimethylamine. D) I is 4-amino-1-butylamine, and II is isopropylmethylamine. (Woods) Ch-15 & The name p-nitroaniline indicates that: A) the NH 2 group is in the 1-position, and the nitro group is in the 2-position on a benzene ring. B) the NH 2 group is in the 1-position, and the nitro group is in the 3-position on a benzene ring. C) the NH 2 group is in the 1-position, and the nitro group is in the 4-position on a benzene ring. D) the NH 2 group is in the 1-position, and the nitro group is in the 5-position on a benzene ring. 35. Arrange these compounds in order of increasing boiling point: I. butane II. 2-methylpropane III. trimethylamine IV. propylamine V. 1-propanol A) II < I < III < IV < V B) II < I < IV < III < V C) V < IV < III < II < I D) I < II < IV < III < V 36. Which statement about these compounds is true? I. butylamine II. 1-butanol A) I has a lower boiling point than II. C) I is more soluble in water than II. B) I and II have about the same boiling point. D) I and II have about the same solubility in water. 37. Which amine can hydrogen bond to itself? I. ethylamine II. diethylamine III. triethylamine A) I and II only B) II and III only C) I and III only D) I, II, and III 38. Arrange these compounds in order of increasing basicity: I. propylamine II. KOH III. aniline IV. 1-propanol A) II < IV < III < II B) III < I < IV < II C) IV < III < I < II D) IV < I < III < II 39. Which compound will have no effect on the color of blue litmus paper? I. propylamine II. 1-propanol III. phenol A) I only B) II only C) II and III only D) I and II only 40. This compound is: CH 3 (CH 2 ) 3 CONHCH 3 A) a secondary amine B) a secondary amide C) a primaryamide D) a tertiary amide 41. Which compounds will react with propylamine? I NaOH II HCl III CH 3 COOH A) I only B) II and III C) III only D) I and III 42. Which compound dissolves in water to produce an alkaline solution? A) CH 3 NH 2 B) CH 3 COOH C) CH 3 CONH 2 D) CH 3 COOCH An unknown is either butylamine or butylammonium chloride. The unknown turns blue litmus paper red. Which statement is correct? A) The unknown is butylamine, because it is a base and bases turn blue litmus paper red. B) The unknown is butylammonium chloride, because it is a base and bases turn blue litmus paper red. C) The unknown is butylamine, because it is an acid and acids turn blue litmus paper red. D) The unknown is butylammonium chloride, because it is an acid and acids turn blue litmus paper red.

5 44. Which compounds react at a temperature greater than 100 C to form this product? (Woods) Ch-15 & I. II. H 2 NCH 2 CH 3 III. IV. H 2 NCH 2 CH 2 CH 3 V. C 6 H 5 NH 2 A) I and IV B) I and II C) I and III D) III and V 45. Hydrolysis of an amide in basic solution produces: A) the anion of a carboxylic acid and an amine C) a carboxylic acid and an amine B) a carboxylic acid and a protonated amine D) a ketone and an amine