{"id":1026,"date":"2016-01-11T20:02:39","date_gmt":"2016-01-11T20:02:39","guid":{"rendered":"https:\/\/opentextbc.ca\/introductorychemistryclone\/chapter\/end-of-chapter-material-32\/"},"modified":"2020-04-20T16:44:00","modified_gmt":"2020-04-20T16:44:00","slug":"end-of-chapter-16-material","status":"publish","type":"chapter","link":"https:\/\/opentextbc.ca\/introductorychemistryclone\/chapter\/end-of-chapter-16-material\/","title":{"raw":"End-of-Chapter Material","rendered":"End-of-Chapter Material"},"content":{"raw":"
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Additional Exercises<\/h3>\r\n
    \r\n \t
  1. \r\n
    \r\n

    Cycloalkanes are named based on the number of C atoms in them, just like regular alkanes, but with the prefix cyclo<\/em>- on the name. What are the names of the three smallest cycloalkanes?<\/p>\r\n\r\n<\/div><\/li>\r\n \t

  2. \r\n
    \r\n

    Cycloalkenes are named similarly to cycloalkanes (see Exercise 1). What are the names of the cycloalkenes with five, six, and seven C atoms?<\/p>\r\n\r\n<\/div><\/li>\r\n \t

  3. \r\n
    \r\n

    Draw the bond-line structure\u00a0of all noncyclic alkanes with only four C atoms.<\/p>\r\n\r\n<\/div><\/li>\r\n \t

  4. \r\n
    \r\n

    Draw the bond-line structure\u00a0of all noncyclic alkanes with only five C atoms.<\/p>\r\n\r\n<\/div><\/li>\r\n \t

  5. \r\n
    \r\n

    Cyclic alkanes can also have substituent groups on the ring. Draw the bond-line structure\u00a0of all cyclic alkanes with only four C atoms.<\/p>\r\n\r\n<\/div><\/li>\r\n \t

  6. \r\n
    \r\n

    Cyclic alkanes can also have substituent groups on the ring. Draw the bond-line structure\u00a0of all cyclic alkanes with only five C atoms.<\/p>\r\n\r\n<\/div><\/li>\r\n \t

  7. \r\n
    \r\n

    Draw and name all possible isomers of pentene.<\/p>\r\n\r\n<\/div><\/li>\r\n \t

  8. \r\n
    \r\n

    Draw and name all possible normal (that is, straight-chain) isomers of heptyne.<\/p>\r\n\r\n<\/div><\/li>\r\n \t

  9. \r\n
    \r\n

    Polyunsaturated alkenes have more than one C\u2013C double bond. Draw the carbon backbone of all possible noncyclic polyunsaturated alkenes with four C atoms and two double bonds. What are the complete molecular formulas for each possible molecule?<\/p>\r\n\r\n<\/div><\/li>\r\n \t

  10. \r\n
    \r\n

    Draw the carbon backbone of all possible five-carbon cyclic alkenes with two double bonds, assuming no substituents on the ring.<\/p>\r\n\r\n<\/div><\/li>\r\n \t

  11. \r\n
    \r\n

    If a hydrocarbon is combined with enough halogen, all the H atoms will eventually be substituted with that halogen atom. Write the balanced chemical reaction between ethane and excess chlorine.<\/p>\r\n\r\n<\/div><\/li>\r\n \t

  12. \r\n
    \r\n

    If a hydrocarbon is combined with enough halogen, all the H atoms will eventually be substituted with that halogen atom. Write the balanced chemical reaction between butane and excess bromine.<\/p>\r\n\r\n<\/div><\/li>\r\n \t

  13. \r\n
    \r\n

    Molecules with multiple double bonds can also participate in addition reactions. Draw the structure of the product when butadiene, CH2<\/sub>=CH\u2013CH=CH2<\/sub>, reacts with chlorine.<\/p>\r\n\r\n<\/div><\/li>\r\n \t

  14. \r\n
    \r\n

    Draw the structure of the product when allene, CH2<\/sub>=C=CH2<\/sub>, reacts with bromine.<\/p>\r\n\r\n<\/div><\/li>\r\n \t

  15. \r\n
    \r\n

    What is the maximum number of methyl groups that can be on a propane backbone before the molecule cannot be named as a propane compound?<\/p>\r\n\r\n<\/div><\/li>\r\n \t

  16. \r\n
    \r\n

    Explain why cycloethane cannot exist as a real molecule.<\/p>\r\n\r\n<\/div><\/li>\r\n \t

  17. \r\n
    \r\n

    In the gasoline industry, what is called isooctane<\/em> is actually 2,2,4-trimethylpentane. Draw the structure of isooctane.<\/p>\r\n\r\n<\/div><\/li>\r\n \t

  18. \r\n
    \r\n

    Isooctane (see Exercise 17) is an isomer of what straight-chain alkane?<\/p>\r\n\r\n<\/div><\/li>\r\n \t

  19. \r\n
    \r\n

    The actual name for the explosive TNT is 2,4,6-trinitrotoluene. If the structure of TNT is as shown below,\u00a0propose the structure of the parent compound toluene.<\/p>\r\n\r\n

    \"ex_19_tnt\"<\/a><\/div>\r\n<\/div><\/li>\r\n \t
  20. \r\n
    \r\n

    Phenol is hydroxybenzene, the simplest aromatic alcohol. Picric acid is an explosive derivative of phenol whose formal name is 2,4,6-trinitrophenol. With reference to Exercise 19, draw the structure of picric acid.<\/p>\r\n\r\n<\/div><\/li>\r\n \t

  21. \r\n
    \r\n

    Draw the structures of all possible straight-chain isomers of bromopentane.<\/p>\r\n\r\n<\/div><\/li>\r\n \t

  22. \r\n
    \r\n

    Draw the structures of all the possible isomers of butanol. Include branched isomers.<\/p>\r\n\r\n<\/div><\/li>\r\n \t

  23. \r\n
    \r\n

    What is the final product of the double<\/em> elimination of HCl from 1,1-dichloroethane?<\/p>\r\n\r\n<\/div><\/li>\r\n \t

  24. \r\n
    \r\n

    Draw the structure of the final product of the double<\/em> elimination of 1,3-dibromopropane.<\/p>\r\n\r\n<\/div><\/li>\r\n \t

  25. \r\n
    \r\n

    Draw the structure of and name the alcohol whose double elimination would yield the same product as in Exercise 23. Name the molecule as a hydroxyl-substituted compound.<\/p>\r\n\r\n<\/div><\/li>\r\n \t

  26. \r\n
    \r\n

    Draw the structure of and name the alcohol whose double elimination would yield the same product as in Exercise 24. Name the molecule as a hydroxyl-substituted compound.<\/p>\r\n\r\n<\/div><\/li>\r\n \t

  27. \r\n
    \r\n

    Draw the smallest molecule that can have a separate aldehyde and carboxylic acid group.<\/p>\r\n\r\n<\/div><\/li>\r\n \t

  28. \r\n
    \r\n

    Name the functional group(s) in the following structure:<\/p>\r\n\r\n

    \"ex_28\"<\/a><\/div>\r\n<\/div><\/li>\r\n \t
  29. \r\n
    \r\n

    Ethyl acetate is a common ingredient in nail-polish remover because it is a good solvent. Draw the structure of ethyl acetate.<\/p>\r\n\r\n<\/div><\/li>\r\n \t

  30. \r\n
    \r\n

    A lactone is an ester that has its ester functional group in a ring. Draw the structure of the smallest possible lactone. (It is called acetolactone, which might give you a hint about its structure.)<\/p>\r\n\r\n<\/div><\/li>\r\n \t

  31. \r\n
    \r\n

    Draw the structure of diethyl ether, once used as an anesthetic.<\/p>\r\n\r\n<\/div><\/li>\r\n \t

  32. \r\n
    \r\n

    The smallest cyclic ether is called an epoxide. Draw its structure.<\/p>\r\n\r\n<\/div><\/li>\r\n \t

  33. \r\n
    \r\n

    Write the chemical reaction of HCl with trimethylamine.<\/p>\r\n\r\n<\/div><\/li>\r\n \t

  34. \r\n
    \r\n

    Putrescine and cadaverine are molecules with two amine groups on the opposite ends of a butane backbone and a pentane backbone, respectively. They are both emitted by rotting corpses. Draw their structures and determine their molecular formulas.<\/p>\r\n\r\n<\/div><\/li>\r\n \t

  35. \r\n
    \r\n

    With four monomers, draw two possible structures of a copolymer composed of ethylene and propylene.<\/p>\r\n\r\n<\/div><\/li>\r\n \t

  36. \r\n
    \r\n

    With four monomers, draw two possible structures of a copolymer composed of ethylene and styrene.<\/p>\r\n\r\n<\/div><\/li>\r\n \t

  37. \r\n
    \r\n

    Draw the silicone that can be made from this monomer:<\/p>\r\n

    \"Question<\/a><\/p>\r\n\r\n

    <\/div>\r\n<\/div><\/li>\r\n \t
  38. \r\n
    \r\n

    One of the ingredients in the original Silly Putty was a silicone polymer with two methyl groups on each Si atom. Draw this silicone.<\/p>\r\n\r\n<\/div><\/li>\r\n<\/ol>\r\n<\/div>\r\n<\/div>\r\n

    \r\n
    \r\n

    Answers<\/h3>\r\n1.\u00a0cyclopropane, cyclobutane, and cyclopentane\r\n\r\n3.\r\n\r\n\"ex_3_sol\"<\/a>\r\n\r\n5.\r\n\r\n\"ex_5_sol\"<\/a>\r\n\r\n7.\r\n\r\n\"ex_7_sol\"<\/a>\r\n\r\n9.\r\n
    \"ex_9_sol\"<\/a><\/div>\r\nBoth molecular formulas are C4<\/sub>H6<\/sub>.\r\n\r\n11.\u00a0C2<\/sub>H6<\/sub> +\u00a06 Cl2<\/sub> \u2192\u00a0C2<\/sub>Cl6<\/sub> +\u00a06 HCl\r\n\r\n13.\r\n\r\n\"ex_13_sol\"<\/a>\r\n\r\n15.\u00a0two\r\n\r\n17.\r\n\r\n\"ex_17_sol\"<\/a>\r\n\r\n19.\r\n\r\n\"ex_19_sol\"<\/a>\r\n\r\n21.\r\n\r\n\"ex_21_sol\"<\/a>\r\n\r\n23.\u00a0ethyne\r\n\r\n\"ex_23_sol\"<\/a>\r\n\r\n25.\u00a0The names are 1,2-dihydroxyethane and 1,1-dihydroxyethane, respectively.\r\n\r\n27.\r\n\r\n\"ex_27_sol\"<\/a>\r\n\r\n29.\r\n\r\n\"ex_29_sol\"<\/a>\r\n\r\n31.\r\n\r\n\"ex_31_sol\"<\/a>\r\n\r\n33.\u00a0(CH3<\/sub>)3<\/sub>N +\u00a0HCl \u2192\u00a0(CH3<\/sub>)3<\/sub>NHCl\r\n\r\n35.\u00a0(answers will vary)\r\n\r\n\"ex_35_sol\"<\/a>\r\n\r\n37.\r\n\r\n\"Answer<\/a>\r\n\r\n<\/div>\r\n<\/div>\r\n<\/div>","rendered":"
    \n
    \n
    \n

    Additional Exercises<\/h3>\n
      \n
    1. \n
      \n

      Cycloalkanes are named based on the number of C atoms in them, just like regular alkanes, but with the prefix cyclo<\/em>– on the name. What are the names of the three smallest cycloalkanes?<\/p>\n<\/div>\n<\/li>\n

    2. \n
      \n

      Cycloalkenes are named similarly to cycloalkanes (see Exercise 1). What are the names of the cycloalkenes with five, six, and seven C atoms?<\/p>\n<\/div>\n<\/li>\n

    3. \n
      \n

      Draw the bond-line structure\u00a0of all noncyclic alkanes with only four C atoms.<\/p>\n<\/div>\n<\/li>\n

    4. \n
      \n

      Draw the bond-line structure\u00a0of all noncyclic alkanes with only five C atoms.<\/p>\n<\/div>\n<\/li>\n

    5. \n
      \n

      Cyclic alkanes can also have substituent groups on the ring. Draw the bond-line structure\u00a0of all cyclic alkanes with only four C atoms.<\/p>\n<\/div>\n<\/li>\n

    6. \n
      \n

      Cyclic alkanes can also have substituent groups on the ring. Draw the bond-line structure\u00a0of all cyclic alkanes with only five C atoms.<\/p>\n<\/div>\n<\/li>\n

    7. \n
      \n

      Draw and name all possible isomers of pentene.<\/p>\n<\/div>\n<\/li>\n

    8. \n
      \n

      Draw and name all possible normal (that is, straight-chain) isomers of heptyne.<\/p>\n<\/div>\n<\/li>\n

    9. \n
      \n

      Polyunsaturated alkenes have more than one C\u2013C double bond. Draw the carbon backbone of all possible noncyclic polyunsaturated alkenes with four C atoms and two double bonds. What are the complete molecular formulas for each possible molecule?<\/p>\n<\/div>\n<\/li>\n

    10. \n
      \n

      Draw the carbon backbone of all possible five-carbon cyclic alkenes with two double bonds, assuming no substituents on the ring.<\/p>\n<\/div>\n<\/li>\n

    11. \n
      \n

      If a hydrocarbon is combined with enough halogen, all the H atoms will eventually be substituted with that halogen atom. Write the balanced chemical reaction between ethane and excess chlorine.<\/p>\n<\/div>\n<\/li>\n

    12. \n
      \n

      If a hydrocarbon is combined with enough halogen, all the H atoms will eventually be substituted with that halogen atom. Write the balanced chemical reaction between butane and excess bromine.<\/p>\n<\/div>\n<\/li>\n

    13. \n
      \n

      Molecules with multiple double bonds can also participate in addition reactions. Draw the structure of the product when butadiene, CH2<\/sub>=CH\u2013CH=CH2<\/sub>, reacts with chlorine.<\/p>\n<\/div>\n<\/li>\n

    14. \n
      \n

      Draw the structure of the product when allene, CH2<\/sub>=C=CH2<\/sub>, reacts with bromine.<\/p>\n<\/div>\n<\/li>\n

    15. \n
      \n

      What is the maximum number of methyl groups that can be on a propane backbone before the molecule cannot be named as a propane compound?<\/p>\n<\/div>\n<\/li>\n

    16. \n
      \n

      Explain why cycloethane cannot exist as a real molecule.<\/p>\n<\/div>\n<\/li>\n

    17. \n
      \n

      In the gasoline industry, what is called isooctane<\/em> is actually 2,2,4-trimethylpentane. Draw the structure of isooctane.<\/p>\n<\/div>\n<\/li>\n

    18. \n
      \n

      Isooctane (see Exercise 17) is an isomer of what straight-chain alkane?<\/p>\n<\/div>\n<\/li>\n

    19. \n
      \n

      The actual name for the explosive TNT is 2,4,6-trinitrotoluene. If the structure of TNT is as shown below,\u00a0propose the structure of the parent compound toluene.<\/p>\n

      \"ex_19_tnt\"<\/a><\/div>\n<\/div>\n<\/li>\n
    20. \n
      \n

      Phenol is hydroxybenzene, the simplest aromatic alcohol. Picric acid is an explosive derivative of phenol whose formal name is 2,4,6-trinitrophenol. With reference to Exercise 19, draw the structure of picric acid.<\/p>\n<\/div>\n<\/li>\n

    21. \n
      \n

      Draw the structures of all possible straight-chain isomers of bromopentane.<\/p>\n<\/div>\n<\/li>\n

    22. \n
      \n

      Draw the structures of all the possible isomers of butanol. Include branched isomers.<\/p>\n<\/div>\n<\/li>\n

    23. \n
      \n

      What is the final product of the double<\/em> elimination of HCl from 1,1-dichloroethane?<\/p>\n<\/div>\n<\/li>\n

    24. \n
      \n

      Draw the structure of the final product of the double<\/em> elimination of 1,3-dibromopropane.<\/p>\n<\/div>\n<\/li>\n

    25. \n
      \n

      Draw the structure of and name the alcohol whose double elimination would yield the same product as in Exercise 23. Name the molecule as a hydroxyl-substituted compound.<\/p>\n<\/div>\n<\/li>\n

    26. \n
      \n

      Draw the structure of and name the alcohol whose double elimination would yield the same product as in Exercise 24. Name the molecule as a hydroxyl-substituted compound.<\/p>\n<\/div>\n<\/li>\n

    27. \n
      \n

      Draw the smallest molecule that can have a separate aldehyde and carboxylic acid group.<\/p>\n<\/div>\n<\/li>\n

    28. \n
      \n

      Name the functional group(s) in the following structure:<\/p>\n

      \"ex_28\"<\/a><\/div>\n<\/div>\n<\/li>\n
    29. \n
      \n

      Ethyl acetate is a common ingredient in nail-polish remover because it is a good solvent. Draw the structure of ethyl acetate.<\/p>\n<\/div>\n<\/li>\n

    30. \n
      \n

      A lactone is an ester that has its ester functional group in a ring. Draw the structure of the smallest possible lactone. (It is called acetolactone, which might give you a hint about its structure.)<\/p>\n<\/div>\n<\/li>\n

    31. \n
      \n

      Draw the structure of diethyl ether, once used as an anesthetic.<\/p>\n<\/div>\n<\/li>\n

    32. \n
      \n

      The smallest cyclic ether is called an epoxide. Draw its structure.<\/p>\n<\/div>\n<\/li>\n

    33. \n
      \n

      Write the chemical reaction of HCl with trimethylamine.<\/p>\n<\/div>\n<\/li>\n

    34. \n
      \n

      Putrescine and cadaverine are molecules with two amine groups on the opposite ends of a butane backbone and a pentane backbone, respectively. They are both emitted by rotting corpses. Draw their structures and determine their molecular formulas.<\/p>\n<\/div>\n<\/li>\n

    35. \n
      \n

      With four monomers, draw two possible structures of a copolymer composed of ethylene and propylene.<\/p>\n<\/div>\n<\/li>\n

    36. \n
      \n

      With four monomers, draw two possible structures of a copolymer composed of ethylene and styrene.<\/p>\n<\/div>\n<\/li>\n

    37. \n
      \n

      Draw the silicone that can be made from this monomer:<\/p>\n

      \"Question<\/a><\/p>\n

      <\/div>\n<\/div>\n<\/li>\n
    38. \n
      \n

      One of the ingredients in the original Silly Putty was a silicone polymer with two methyl groups on each Si atom. Draw this silicone.<\/p>\n<\/div>\n<\/li>\n<\/ol>\n<\/div>\n<\/div>\n

      \n
      \n

      Answers<\/h3>\n

      1.\u00a0cyclopropane, cyclobutane, and cyclopentane<\/p>\n

      3.
      \n
      \n\"ex_3_sol\"<\/a><\/p>\n

      5.<\/p>\n

      \"ex_5_sol\"<\/a><\/p>\n

      7.<\/p>\n

      \"ex_7_sol\"<\/a><\/p>\n

      9.<\/p>\n

      \"ex_9_sol\"<\/a><\/div>\n

      Both molecular formulas are C4<\/sub>H6<\/sub>.<\/p>\n

      11.\u00a0C2<\/sub>H6<\/sub> +\u00a06 Cl2<\/sub> \u2192\u00a0C2<\/sub>Cl6<\/sub> +\u00a06 HCl<\/p>\n

      13.<\/p>\n

      \"ex_13_sol\"<\/a><\/p>\n

      15.\u00a0two<\/p>\n

      17.<\/p>\n

      \"ex_17_sol\"<\/a><\/p>\n

      19.<\/p>\n

      \"ex_19_sol\"<\/a><\/p>\n

      21.<\/p>\n

      \"ex_21_sol\"<\/a><\/p>\n

      23.\u00a0ethyne<\/p>\n

      \"ex_23_sol\"<\/a><\/p>\n

      25.\u00a0The names are 1,2-dihydroxyethane and 1,1-dihydroxyethane, respectively.<\/p>\n

      27.
      \n
      \n\"ex_27_sol\"<\/a><\/p>\n

      29.<\/p>\n

      \"ex_29_sol\"<\/a><\/p>\n

      31.<\/p>\n

      \"ex_31_sol\"<\/a><\/p>\n

      33.\u00a0(CH3<\/sub>)3<\/sub>N +\u00a0HCl \u2192\u00a0(CH3<\/sub>)3<\/sub>NHCl<\/p>\n

      35.\u00a0(answers will vary)<\/p>\n

      \"ex_35_sol\"<\/a><\/p>\n

      37.<\/p>\n

      \"Answer<\/a><\/p>\n<\/div>\n<\/div>\n<\/div>\n","protected":false},"author":124,"menu_order":7,"template":"","meta":{"pb_show_title":"on","pb_short_title":"","pb_subtitle":"","pb_authors":[],"pb_section_license":""},"chapter-type":[],"contributor":[],"license":[],"class_list":["post-1026","chapter","type-chapter","status-publish","hentry"],"part":819,"_links":{"self":[{"href":"https:\/\/opentextbc.ca\/introductorychemistryclone\/wp-json\/pressbooks\/v2\/chapters\/1026","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/opentextbc.ca\/introductorychemistryclone\/wp-json\/pressbooks\/v2\/chapters"}],"about":[{"href":"https:\/\/opentextbc.ca\/introductorychemistryclone\/wp-json\/wp\/v2\/types\/chapter"}],"author":[{"embeddable":true,"href":"https:\/\/opentextbc.ca\/introductorychemistryclone\/wp-json\/wp\/v2\/users\/124"}],"version-history":[{"count":2,"href":"https:\/\/opentextbc.ca\/introductorychemistryclone\/wp-json\/pressbooks\/v2\/chapters\/1026\/revisions"}],"predecessor-version":[{"id":1445,"href":"https:\/\/opentextbc.ca\/introductorychemistryclone\/wp-json\/pressbooks\/v2\/chapters\/1026\/revisions\/1445"}],"part":[{"href":"https:\/\/opentextbc.ca\/introductorychemistryclone\/wp-json\/pressbooks\/v2\/parts\/819"}],"metadata":[{"href":"https:\/\/opentextbc.ca\/introductorychemistryclone\/wp-json\/pressbooks\/v2\/chapters\/1026\/metadata\/"}],"wp:attachment":[{"href":"https:\/\/opentextbc.ca\/introductorychemistryclone\/wp-json\/wp\/v2\/media?parent=1026"}],"wp:term":[{"taxonomy":"chapter-type","embeddable":true,"href":"https:\/\/opentextbc.ca\/introductorychemistryclone\/wp-json\/pressbooks\/v2\/chapter-type?post=1026"},{"taxonomy":"contributor","embeddable":true,"href":"https:\/\/opentextbc.ca\/introductorychemistryclone\/wp-json\/wp\/v2\/contributor?post=1026"},{"taxonomy":"license","embeddable":true,"href":"https:\/\/opentextbc.ca\/introductorychemistryclone\/wp-json\/wp\/v2\/license?post=1026"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}