{"id":3870,"date":"2018-05-25T19:04:45","date_gmt":"2018-05-25T23:04:45","guid":{"rendered":"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/?post_type=chapter&p=3870"},"modified":"2019-05-14T18:09:51","modified_gmt":"2019-05-14T22:09:51","slug":"9-x-end-of-chapter-problems-langara","status":"publish","type":"chapter","link":"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/chapter\/9-x-end-of-chapter-problems-langara\/","title":{"raw":"10.8 End of Chapter Problems","rendered":"10.8 End of Chapter Problems"},"content":{"raw":"
\r\n\r\n1. Draw the line bond structure for the following compounds:\r\n\r\na) Br[CH(CH3<\/sub>)]4<\/sub>COCH(CH3<\/sub>)CH2<\/sub>CH3<\/sub>\r\n\r\nb) CH3<\/sub>(CH)8<\/sub>CH2<\/sub>COOH\r\n\r\nc) CH3<\/sub>CH2<\/sub>CH(CHO)(CH2<\/sub>)2<\/sub>CH(CH3<\/sub>)CH2<\/sub>Br\r\n\r\nd) (HO)2<\/sub>CH(CH2<\/sub>)2<\/sub>O(CH2<\/sub>)3<\/sub>COOH\r\n\r\n2. For the following compounds, give the chemical formula and the condensed structure:\r\n\r\n\"\"\r\n\r\n3. Answer the following questions for each of these compounds.\r\n\r\na) Name the circled functional groups: A = ?, \u00a0B = ?, C = ?\r\n\r\nb) What is the chemical formula of the compound?\r\n\r\nc) How many lone pairs are there in the compound?\r\n\r\nPhenylalanine\u00a0<\/strong>is an \u03b1-amino acid.\r\n\r\n\"\"\r\n\r\nAspirin<\/strong>, also known as acetylsalicylic acid<\/strong>, is often used\u00a0to relieve minor aches and pains, and\u00a0to reduce fever.\r\n\r\n\"\"\r\n\r\nTetracycline\u00a0<\/strong>is an antibiotic used against many bacterial infections.\r\n\r\n\"\"\r\n\r\nAmpicillin\u00a0<\/strong>is an antibiotic used against many bacterial infections\u00a0since 1961.\r\n\r\n\"\"\r\n\r\nForskolin<\/strong> is a natural product produced by the Indian Coleus plant\u00a0(Coleus forskohlii<\/em>).\r\n\r\n\"\"\r\n

4. 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

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

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

7. 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?<\/span><\/p>\r\n

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

9. 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.<\/span><\/p>\r\n\r\n<\/div>\r\n

\r\n
\"ex_19_tnt\"<\/a><\/div>\r\n
10. Draw the smallest molecule that can have a separate aldehyde and carboxylic acid group.<\/span><\/div>\r\n
11. Name the functional group(s) in the following structure:<\/span><\/div>\r\n<\/div>\r\n
\r\n
\"ex_28\"<\/a><\/div>\r\n
12. Ethyl acetate is a common ingredient in nail-polish remover because it is a good solvent. Its IUPAC name is ethyl ethanoate.\u00a0 Draw the structure of ethyl acetate.<\/span><\/div>\r\n
13. Draw the structure of diethyl ether, once used as an anesthetic.<\/span><\/div>\r\n
14. Write the chemical reaction of HCl with trimethylamine.<\/span><\/div>\r\n<\/div>\r\n
15.Give the IUPAC name the following organic compounds.<\/span><\/span><\/div>\r\n
\"\"<\/div>\r\n
\"\"<\/div>\r\n
<\/div>\r\n
<\/div>\r\n
\r\n

Answers<\/strong><\/h2>\r\n<\/div>\r\n1.\"\"\r\n\r\n2.\u00a0\u00a0a) C8<\/sub>H12<\/sub>O4<\/sub>\u00a0 \u00a0 \u00a0 HOOCCH2<\/sub>COCH2<\/sub>CO(CH2<\/sub>)2<\/sub>CH3<\/sub>\r\n\r\nb) C8<\/sub>H10<\/sub>O3<\/sub>\u00a0 \u00a0 \u00a0 \u00a0 \u00a0HOC(CH)4<\/sub>(CH2<\/sub>)2<\/sub>COOH\r\n\r\nc) C14<\/sub>H28 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0<\/sub>CH3<\/sub>(CH)2<\/sub>CH(CH[CH3<\/sub>]CH2<\/sub>CH3<\/sub>)(CH2<\/sub>)5<\/sub>CH3<\/sub>\r\n\r\nd) C9<\/sub>H17<\/sub>Cl \u00a0 \u00a0 \u00a0 \u00a0Cl(CH2<\/sub>)2<\/sub>C(CHCH2<\/sub>CH3<\/sub>)(CH2<\/sub>)2<\/sub>CH3<\/sub>\r\n\r\n3.\u00a0Phenylalanine\u00a0<\/strong>a) A = Arene, B = Carboxylic Acid, C = Primary Amine\r\n\r\nb) C9<\/sub>H11<\/sub>NO2<\/sub>\r\n\r\nc) 5 lone pairs \u2013 one on the nitrogen and two on each oxygen,\r\n\r\nAspirin<\/strong>\u00a0a) A = Ester, B = Arene, C = Carboxylic Acid\r\n\r\nb) C9<\/sub>H8<\/sub>O4<\/sub>\r\n\r\nc) 8 lone pairs \u2013 two on each oxygen,\r\n\r\nTetracycline<\/strong>\u00a0a) A = Tertiary Alcohol, B = Tertiary Amine, C = Ketone\r\n\r\nb) C22<\/sub>H24<\/sub>N2<\/sub>O8<\/sub>\r\n\r\nc) 18 lone pairs \u2013 one on each nitrogen and two on each oxygen\r\n\r\nAmpicillin \u00a0<\/strong>a) A = Tertiary Amide, B = Carboxylic Acid, C = Arene\r\n\r\nb) C16<\/sub>H19<\/sub>N3<\/sub>O4<\/sub>S\r\n\r\nc) 13 lone pairs \u2013 one on each nitrogen, two on each oxygen and two on the sulfur\r\n\r\nForskolin<\/strong>\u00a0a) A = Secondary Alcohol, B = Ether, C = Ketone\r\n\r\nb) C22<\/sub>H34<\/sub>O7<\/sub>\r\n\r\nc) 14 lone pairs \u2013two on each oxygen,\r\n\r\n4.\u00a0cyclopropane, cyclobutane, and cyclopentane\r\n\r\n5.\r\n\"ex_3_sol\"<\/a>\r\n\r\n6.\r\n\r\n\"ex_5_sol\"<\/a>\r\n\r\n7.\u00a0two\r\n\r\n8.\r\n\r\n\"\"<\/a>\r\n\r\n \r\n\r\n \r\n\r\n \r\n\r\n \r\n\r\n9.\r\n\r\n\"ex_19_sol\"<\/a>\r\n\r\n10.\r\n\"ex_27_sol\"<\/a>\r\n\r\n11. alcohol (or more specifically phenol), arene, ketone, primary amine\r\n\r\n12.\r\n\r\n\"ex_29_sol\"<\/a>\r\n\r\n13.\r\n\r\n\"ex_31_sol\"<\/a>\r\n\r\n14. Triethylamine is a base and HCl is an acid, therefore you get an acid-base reaction.\r\n\r\n(CH3<\/sub>)3<\/sub>N +\u00a0HCl $latex \\longrightarrow$<\/span><\/span> (CH3<\/sub>)3<\/sub>NHCl\r\n\r\n15.\u00a0a) 4-ethyloctane\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 b) 3-ethyl-2,4-dimethylhexane\r\n\r\nc) 2,4-dibromo-1-chloro-3-methylpentane \u00a0 \u00a0 \u00a0 \u00a0d) 5,5-dimethyl-3-propyl-1-heptene\r\n\r\ne) 4-methyl-4-octene \u00a0 \u00a0 \u00a0f)\u00a0 2-ethyl-1,6-heptadiene \u00a0 \u00a0 \u00a0 g) 3-ethyl-1,4-hexadiene\r\n\r\nh) 4-ethyl-2,5-octadiene \u00a0 \u00a0 i) 3,3-dimethyl-4-octyne \u00a0 \u00a0 \u00a0 j) 4-methyl-2-hexyne","rendered":"
\n

1. Draw the line bond structure for the following compounds:<\/p>\n

a) Br[CH(CH3<\/sub>)]4<\/sub>COCH(CH3<\/sub>)CH2<\/sub>CH3<\/sub><\/p>\n

b) CH3<\/sub>(CH)8<\/sub>CH2<\/sub>COOH<\/p>\n

c) CH3<\/sub>CH2<\/sub>CH(CHO)(CH2<\/sub>)2<\/sub>CH(CH3<\/sub>)CH2<\/sub>Br<\/p>\n

d) (HO)2<\/sub>CH(CH2<\/sub>)2<\/sub>O(CH2<\/sub>)3<\/sub>COOH<\/p>\n

2. For the following compounds, give the chemical formula and the condensed structure:<\/p>\n

\"\"<\/p>\n

3. Answer the following questions for each of these compounds.<\/p>\n

a) Name the circled functional groups: A = ?, \u00a0B = ?, C = ?<\/p>\n

b) What is the chemical formula of the compound?<\/p>\n

c) How many lone pairs are there in the compound?<\/p>\n

Phenylalanine\u00a0<\/strong>is an \u03b1-amino acid.<\/p>\n

\"\"<\/p>\n

Aspirin<\/strong>, also known as acetylsalicylic acid<\/strong>, is often used\u00a0to relieve minor aches and pains, and\u00a0to reduce fever.<\/p>\n

\"\"<\/p>\n

Tetracycline\u00a0<\/strong>is an antibiotic used against many bacterial infections.<\/p>\n

\"\"<\/p>\n

Ampicillin\u00a0<\/strong>is an antibiotic used against many bacterial infections\u00a0since 1961.<\/p>\n

\"\"<\/p>\n

Forskolin<\/strong> is a natural product produced by the Indian Coleus plant\u00a0(Coleus forskohlii<\/em>).<\/p>\n

\"\"<\/p>\n

4. 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

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

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

7. 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?<\/span><\/p>\n

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

9. 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.<\/span><\/p>\n<\/div>\n

\n
\"ex_19_tnt\"<\/a><\/div>\n
10. Draw the smallest molecule that can have a separate aldehyde and carboxylic acid group.<\/span><\/div>\n
11. Name the functional group(s) in the following structure:<\/span><\/div>\n<\/div>\n
\n
\"ex_28\"<\/a><\/div>\n
12. Ethyl acetate is a common ingredient in nail-polish remover because it is a good solvent. Its IUPAC name is ethyl ethanoate.\u00a0 Draw the structure of ethyl acetate.<\/span><\/div>\n
13. Draw the structure of diethyl ether, once used as an anesthetic.<\/span><\/div>\n
14. Write the chemical reaction of HCl with trimethylamine.<\/span><\/div>\n<\/div>\n
15.Give the IUPAC name the following organic compounds.<\/span><\/span><\/div>\n
\"\"<\/div>\n
\"\"<\/div>\n
<\/div>\n
<\/div>\n
\n

Answers<\/strong><\/h2>\n<\/div>\n

1.\"\"<\/p>\n

2.\u00a0\u00a0a) C8<\/sub>H12<\/sub>O4<\/sub>\u00a0 \u00a0 \u00a0 HOOCCH2<\/sub>COCH2<\/sub>CO(CH2<\/sub>)2<\/sub>CH3<\/sub><\/p>\n

b) C8<\/sub>H10<\/sub>O3<\/sub>\u00a0 \u00a0 \u00a0 \u00a0 \u00a0HOC(CH)4<\/sub>(CH2<\/sub>)2<\/sub>COOH<\/p>\n

c) C14<\/sub>H28 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0 \u00a0<\/sub>CH3<\/sub>(CH)2<\/sub>CH(CH[CH3<\/sub>]CH2<\/sub>CH3<\/sub>)(CH2<\/sub>)5<\/sub>CH3<\/sub><\/p>\n

d) C9<\/sub>H17<\/sub>Cl \u00a0 \u00a0 \u00a0 \u00a0Cl(CH2<\/sub>)2<\/sub>C(CHCH2<\/sub>CH3<\/sub>)(CH2<\/sub>)2<\/sub>CH3<\/sub><\/p>\n

3.\u00a0Phenylalanine\u00a0<\/strong>a) A = Arene, B = Carboxylic Acid, C = Primary Amine<\/p>\n

b) C9<\/sub>H11<\/sub>NO2<\/sub><\/p>\n

c) 5 lone pairs \u2013 one on the nitrogen and two on each oxygen,<\/p>\n

Aspirin<\/strong>\u00a0a) A = Ester, B = Arene, C = Carboxylic Acid<\/p>\n

b) C9<\/sub>H8<\/sub>O4<\/sub><\/p>\n

c) 8 lone pairs \u2013 two on each oxygen,<\/p>\n

Tetracycline<\/strong>\u00a0a) A = Tertiary Alcohol, B = Tertiary Amine, C = Ketone<\/p>\n

b) C22<\/sub>H24<\/sub>N2<\/sub>O8<\/sub><\/p>\n

c) 18 lone pairs \u2013 one on each nitrogen and two on each oxygen<\/p>\n

Ampicillin \u00a0<\/strong>a) A = Tertiary Amide, B = Carboxylic Acid, C = Arene<\/p>\n

b) C16<\/sub>H19<\/sub>N3<\/sub>O4<\/sub>S<\/p>\n

c) 13 lone pairs \u2013 one on each nitrogen, two on each oxygen and two on the sulfur<\/p>\n

Forskolin<\/strong>\u00a0a) A = Secondary Alcohol, B = Ether, C = Ketone<\/p>\n

b) C22<\/sub>H34<\/sub>O7<\/sub><\/p>\n

c) 14 lone pairs \u2013two on each oxygen,<\/p>\n

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

5.
\n\"ex_3_sol\"<\/a><\/p>\n

6.<\/p>\n

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

7.\u00a0two<\/p>\n

8.<\/p>\n

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

 <\/p>\n

 <\/p>\n

 <\/p>\n

 <\/p>\n

9.<\/p>\n

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

10.
\n\"ex_27_sol\"<\/a><\/p>\n

11. alcohol (or more specifically phenol), arene, ketone, primary amine<\/p>\n

12.<\/p>\n

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

13.<\/p>\n

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

14. Triethylamine is a base and HCl is an acid, therefore you get an acid-base reaction.<\/p>\n

(CH3<\/sub>)3<\/sub>N +\u00a0HCl [latex]\\longrightarrow[\/latex]<\/span><\/span> (CH3<\/sub>)3<\/sub>NHCl<\/p>\n

15.\u00a0a) 4-ethyloctane\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0\u00a0 b) 3-ethyl-2,4-dimethylhexane<\/p>\n

c) 2,4-dibromo-1-chloro-3-methylpentane \u00a0 \u00a0 \u00a0 \u00a0d) 5,5-dimethyl-3-propyl-1-heptene<\/p>\n

e) 4-methyl-4-octene \u00a0 \u00a0 \u00a0f)\u00a0 2-ethyl-1,6-heptadiene \u00a0 \u00a0 \u00a0 g) 3-ethyl-1,4-hexadiene<\/p>\n

h) 4-ethyl-2,5-octadiene \u00a0 \u00a0 i) 3,3-dimethyl-4-octyne \u00a0 \u00a0 \u00a0 j) 4-methyl-2-hexyne<\/p>\n","protected":false},"author":330,"menu_order":9,"template":"","meta":{"pb_show_title":"on","pb_short_title":"10.8 End of Chapter Problems","pb_subtitle":"","pb_authors":[],"pb_section_license":"cc-by-nc-sa"},"chapter-type":[],"contributor":[],"license":[54],"class_list":["post-3870","chapter","type-chapter","status-publish","hentry","license-cc-by-nc-sa"],"part":1829,"_links":{"self":[{"href":"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-json\/pressbooks\/v2\/chapters\/3870","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-json\/pressbooks\/v2\/chapters"}],"about":[{"href":"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-json\/wp\/v2\/types\/chapter"}],"author":[{"embeddable":true,"href":"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-json\/wp\/v2\/users\/330"}],"version-history":[{"count":15,"href":"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-json\/pressbooks\/v2\/chapters\/3870\/revisions"}],"predecessor-version":[{"id":4040,"href":"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-json\/pressbooks\/v2\/chapters\/3870\/revisions\/4040"}],"part":[{"href":"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-json\/pressbooks\/v2\/parts\/1829"}],"metadata":[{"href":"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-json\/pressbooks\/v2\/chapters\/3870\/metadata\/"}],"wp:attachment":[{"href":"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-json\/wp\/v2\/media?parent=3870"}],"wp:term":[{"taxonomy":"chapter-type","embeddable":true,"href":"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-json\/pressbooks\/v2\/chapter-type?post=3870"},{"taxonomy":"contributor","embeddable":true,"href":"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-json\/wp\/v2\/contributor?post=3870"},{"taxonomy":"license","embeddable":true,"href":"https:\/\/pressbooks.bccampus.ca\/chem1114langaracollege\/wp-json\/wp\/v2\/license?post=3870"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}