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1 Chapter 2 - Alkanes: The Nature of Organic Compounds 1. Which of the following functional group classifications do not contain oxygen? A. ether B. thiol C. aldehyde D. ester E. amide 2. To which functional group classification does the following molecule belong? A. ester B. ketone C. alcohol D. carboxylic acid E. both b and c 3. One of the functional group classifications is characterized by the presence of an sp 2 hybridized carbon atom. This functional group could be: A. alkyl halide B. sulfide C. alcohol D. aldehyde E. alkyne 4. The carbon atoms within the functional group of the following classifications are: alkene ester carboxylic acid amide A. sp B. sp 2 C. sp 3 D. sp 2 and sp 3
2 5. 4-ethyl-3,3,4-trimethylheptane could be classified as: A. an alkane B. saturated C. aliphatic D. a paraffin E. all of these 6. 4-ethyl-3,3,4-trimethylheptane contains: A. two quaternary carbon atoms B. two tertiary carbon atoms C. four secondary carbon atoms D. a and c E. all of these 7. Circle and name each functional group in the following structure. cortisone acetate (active ingredient in steroid skin cream)
3 8. Label the following pair of compounds as: A. identical B. constitutional isomers C. stereoisomers D. unrelated 9. Provide a skeletal structure for 5-tert-butyl-2,3-dimethyloctane. 10. Provide a proper IUPAC name for the compound given below.
4 11. Draw the structure of a five carbon ketone containing one tertiary carbon atom. 12. Which hydrogen atom(s) in the following compound is (are) classified as tertiary? A. a B. b C. c D. both a and c E. There are no tertiary hydrogen atoms. 13. Instructions: Label each pair of compounds below as: 1. constitutional isomers 2. identical, but differing in conformation
5 14. How many constitutional isomers are there with the molecular formula C6H14? A. 3 B. 4 C. 5 D What is the IUPAC name of the following compound? A. 2-ethyl-4-methylpentane B. 2,4-dimethylhexane C. 3,5-dimethylhexane D. 1,1,3-trimethylpentane 16. Which of the following alkanes is the most likely to be a liquid at room temperature? A. propane B. butane C. pentane D. hexane 17. Name these groups (left to right). where represents the parent chain. A. sec-propyl, sec-butyl, isobutyl B. isopropyl, isobutyl, sec-butyl C. sec-propyl, tert-butyl, isobutyl D. isopropyl, tert-butyl, isobutyl E. isopropyl, tert-butyl, sec-butyl
6 18. Designate each carbon as primary, secondary, tertiary, or quaternary. 19. Instructions: Label each pair of compounds below as: 1. stereoisomers 2. identical 20. Provide the proper IUPAC name for the compound below.
7 21. Draw and name the seven constitutional isomers for cycloalkane, C6H Instructions: Refer to the structure below to answer the following question(s). Refer to instructions. Which of the labeled groups in the structure are equatorial?
8 23. Instructions: Refer to the structure below to answer the following question(s). Refer to instructions. Which of the labeled groups is trans to b? 24. Instructions: Refer to the structure below to answer the following question(s). Refer to instructions. Which groups have a 1,3-diaxial interaction with each other?
9 25. Instructions: For each disubstituted cyclohexane below, draw its ring-flip isomer. Circle the most stable conformation and label the substituent groups as axial or equatorial. Draw and label: 26. Instructions: For each disubstituted cyclohexane below, draw its ring-flip isomer. Circle the most stable conformation and label the substituent groups as axial or equatorial. Draw and label: 27. Instructions: Label each pair of compounds below as: a. identical b. stereoisomers c. constitutional isomers d. identical, but differing in conformation
10 Where stereoisomers are present, label the isomers as cis and trans. Label: and 28. Instructions: Label each pair of compounds below as: a. identical b. stereoisomers c. constitutional isomers d. identical, but differing in conformation Where stereoisomers are present, label the isomers as cis and trans. Label: and
11 29. Which of the following cycloalkanes has the most ring strain? A. cyclopropane B. cyclobutane C. cyclopentane D. cyclohexane 30. In which of the following compounds would the carbon-carbon bond angle diverge the greatest from 109? A. cyclodecane B. cyclooctane C. cyclopentane D. cyclopropane 31. Substitution of which of the following groups on a cycloalkane would result in the greatest amount of steric strain? A. bromo B. ethyl C. isopropyl D. hydroxyl 32. Which of the following structures represents trans-1,3-dimethylcyclohexane? A. B. C. D.
12 33. Which of the following structures represents trans-1,2-dimethylcyclohexane? A. B. C. D. 34. Which of the following is the most stable conformation of cis-1-isopropyl-3-methylcyclohexane? A. B. C. D.
13 35. Which of the following is the most stable conformation of trans-1-ethyl-3-methylcyclohexane? A. B. C. D. 36. Instructions: (-)-Menthol is responsible for the characteristic flavor and taste of peppermint. The structure of (-)-menthol is shown below. Use this information to answer the following question. Refer to instructions. On the chair template provided below, draw the two chair conformations that are in equilibrium for (-)-menthol.
14 37. D-Pinitol is an interesting hexahydroxycyclohexane, whose structure is shown below. On the templates provided, draw the two chair conformations that are in equilibrium for D-pinitol. Circle the most stable conformation. 38. Draw two isomeric alcohols with the formula C4H10O.
15 39. This skeletal structure corresponds to the molecular formula: a. C5H6O6 b. C7H10O6 c. C6H6O6 d. C6H8O6
16 40. Instructions: MATCH a structure below to each of the following descriptions and place the letter corresponding to the structure in the blank. Refer to Instructions. is an amino aldehyde.
17 41. Instructions: MATCH a structure below to each of the following descriptions and place the letter corresponding to the structure in the blank. Refer to Instructions. is an aromatic ketone.
18 42. Instructions: MATCH a structure below to each of the following descriptions and place the letter corresponding to the structure in the blank. Refer to Instructions. is a tertiary chloride.
19 43. Instructions: MATCH a structure below to each of the following descriptions and place the letter corresponding to the structure in the blank. Refer to Instructions. is a cyclic alkane with two cis methyl groups. 44. Draw a structure corresponding to the following name: cis-1-sec-butyl-2-ethylcyclopentane
20 45. Instructions: Full file at Consider the conformations of 2-methylbutane shown below to answer the following questions. Refer to Instructions. Which of the structures represents the most stable conformation of 2-methylbutane? 46. Instructions: Consider the conformations of 2-methylbutane shown below to answer the following questions. Refer to Instructions. Which of the structures represents the least stable conformation of 2-methylbutane?
21 47. Draw the Newman projection for the specified conformations for rotation about the C-C bond of 1,2-dichloroethane. There are two staggered conformations of 1,2-dichloroethane. Draw them. 48. Draw the Newman projection for the specified conformations for rotation about the C-C bond of 1,2-dichloroethane. There are two eclipsed conformations of 1,2-dichloroethane. Draw them.
22 Chapter 2 - Alkanes: The Nature of Organic Compounds Key 1. Which of the following functional group classifications do not contain oxygen? A. ether B. thiol C. aldehyde D. ester E. amide 2. To which functional group classification does the following molecule belong? A. ester B. ketone C. alcohol D. carboxylic acid E. both b and c 3. One of the functional group classifications is characterized by the presence of an sp 2 hybridized carbon atom. This functional group could be: A. alkyl halide B. sulfide C. alcohol D. aldehyde E. alkyne 4. The carbon atoms within the functional group of the following classifications are: alkene ester carboxylic acid amide A. sp B. sp 2 C. sp 3 D. sp 2 and sp 3
23 5. 4-ethyl-3,3,4-trimethylheptane could be classified as: A. an alkane B. saturated C. aliphatic D. a paraffin E. all of these 6. 4-ethyl-3,3,4-trimethylheptane contains: A. two quaternary carbon atoms B. two tertiary carbon atoms C. four secondary carbon atoms D. a and c E. all of these 7. Circle and name each functional group in the following structure. cortisone acetate (active ingredient in steroid skin cream)
24 8. Label the following pair of compounds as: A. identical B. constitutional isomers C. stereoisomers D. unrelated 9. Provide a skeletal structure for 5-tert-butyl-2,3-dimethyloctane.
25 10. Provide a proper IUPAC name for the compound given below. 3-methyl-5-isopropyloctane or 3-methyl-5-(1-methylethyl)octane 11. Draw the structure of a five carbon ketone containing one tertiary carbon atom. 12. Which hydrogen atom(s) in the following compound is (are) classified as tertiary? A. a B. b C. c D. both a and c E. There are no tertiary hydrogen atoms.
26 13. Instructions: Label each pair of compounds below as: 1. constitutional isomers 1 2. identical, but differing in conformation How many constitutional isomers are there with the molecular formula C6H14? A. 3 B. 4 C. 5 D What is the IUPAC name of the following compound? A. 2-ethyl-4-methylpentane B. 2,4-dimethylhexane C. 3,5-dimethylhexane D. 1,1,3-trimethylpentane 16. Which of the following alkanes is the most likely to be a liquid at room temperature? A. propane B. butane C. pentane D. hexane
27 17. Name these groups (left to right). where represents the parent chain. A. sec-propyl, sec-butyl, isobutyl B. isopropyl, isobutyl, sec-butyl C. sec-propyl, tert-butyl, isobutyl D. isopropyl, tert-butyl, isobutyl E. isopropyl, tert-butyl, sec-butyl 18. Designate each carbon as primary, secondary, tertiary, or quaternary. 19. Instructions: Label each pair of compounds below as: 1. stereoisomers 2 2. identical 1
28 20. Provide the proper IUPAC name for the compound below. trans-1-tert-butyl-4-ethylcyclohexane or trans-1-(1,1-dimethylethyl)-4-ethylcyclohexane 21. Draw and name the seven constitutional isomers for cycloalkane, C6H12. cyclohexane methylcyclopentane 1,2-dimethylc yclobutane 1,2-dimethylcyclobutane 1,1-dimethylcyclobutane 1,2,3-trimethylcyclop ropane 1,1,2-trimethyl cyclopropane 22. Instructions: Refer to the structure below to answer the following question(s). Refer to instructions. Which of the labeled groups in the structure are equatorial? a and d
29 23. Instructions: Refer to the structure below to answer the following question(s). e Refer to instructions. Which of the labeled groups is trans to b? 24. Instructions: Refer to the structure below to answer the following question(s). Refer to instructions. Which groups have a 1,3-diaxial interaction with each other? b and c 25. Instructions: For each disubstituted cyclohexane below, draw its ring-flip isomer. Circle the most stable conformation and label the substituent groups as axial or equatorial. Draw and label: conformations are of equal stability
30 26. Instructions: For each disubstituted cyclohexane below, draw its ring-flip isomer. Circle the most stable conformation and label the substituent groups as axial or equatorial. Draw and label: 27. Instructions: Label each pair of compounds below as: a. identical b. stereoisomers c. constitutional isomers d. identical, but differing in conformation Where stereoisomers are present, label the isomers as cis and trans. Label: and b trans cis
31 28. Instructions: Label each pair of compounds below as: a. identical b. stereoisomers c. constitutional isomers d. identical, but differing in conformation Where stereoisomers are present, label the isomers as cis and trans. Label: and a 29. Which of the following cycloalkanes has the most ring strain? A. cyclopropane B. cyclobutane C. cyclopentane D. cyclohexane 30. In which of the following compounds would the carbon-carbon bond angle diverge the greatest from 109? A. cyclodecane B. cyclooctane C. cyclopentane D. cyclopropane 31. Substitution of which of the following groups on a cycloalkane would result in the greatest amount of steric strain? A. bromo B. ethyl C. isopropyl D. hydroxyl
32 32. Which of the following structures represents trans-1,3-dimethylcyclohexane? A. B. C. D. 33. Which of the following structures represents trans-1,2-dimethylcyclohexane? A. B. C. D.
33 34. Which of the following is the most stable conformation of cis-1-isopropyl-3-methylcyclohexane? A. B. C. D. 35. Which of the following is the most stable conformation of trans-1-ethyl-3-methylcyclohexane? A. B. C. D.
34 36. Instructions: (-)-Menthol is responsible for the characteristic flavor and taste of peppermint. The structure of (-)-menthol is shown below. Use this information to answer the following question. Refer to instructions. On the chair template provided below, draw the two chair conformations that are in equilibrium for (-)-menthol.
35 37. D-Pinitol is an interesting hexahydroxycyclohexane, whose structure is shown below. On the templates provided, draw the two chair conformations that are in equilibrium for D-pinitol. Circle the most stable conformation. 38. Draw two isomeric alcohols with the formula C4H10O.
36 39. This skeletal structure corresponds to the molecular formula: a. C5H6O6 b. C7H10O6 c. C6H6O6 d. C6H8O6 d 40. Instructions: MATCH a structure below to each of the following descriptions and place the letter corresponding to the structure in the blank. B Refer to Instructions. is an amino aldehyde.
37 41. Instructions: MATCH a structure below to each of the following descriptions and place the letter corresponding to the structure in the blank. E Refer to Instructions. is an aromatic ketone. 42. Instructions: MATCH a structure below to each of the following descriptions and place the letter corresponding to the structure in the blank. C Refer to Instructions. is a tertiary chloride.
38 43. Instructions: MATCH a structure below to each of the following descriptions and place the letter corresponding to the structure in the blank. C Refer to Instructions. is a cyclic alkane with two cis methyl groups. 44. Draw a structure corresponding to the following name: cis-1-sec-butyl-2-ethylcyclopentane
39 45. Instructions: Full file at Consider the conformations of 2-methylbutane shown below to answer the following questions. A Refer to Instructions. Which of the structures represents the most stable conformation of 2-methylbutane? 46. Instructions: Consider the conformations of 2-methylbutane shown below to answer the following questions. B Refer to Instructions. Which of the structures represents the least stable conformation of 2-methylbutane? 47. Draw the Newman projection for the specified conformations for rotation about the C-C bond of 1,2-dichloroethane. There are two staggered conformations of 1,2-dichloroethane. Draw them.
40 48. Draw the Newman projection for the specified conformations for rotation about the C-C bond of 1,2-dichloroethane. There are two eclipsed conformations of 1,2-dichloroethane. Draw them.
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