hem 201 Page 1 of 20 24 TE UNIVERSITY F ALGARY FAULTY F SIENE EMISTRY 201 FALL 2015 FINAL EXAMINATIN Written Mark Written Mark Q19 Q22 Q20 Q23 Q21 DATE: Dec 14 th, 2015 TIME: 3 ours FIRST NAME: LAST NAME: ID: Lecture Section: Please check one, then fill in ID # on next page! L01 MWF 1:00 pm Dr. E. Sullivan L02 MWF 2:00 pm Dr. V. Mozol L03 TR 9:30 am Dr. E. Sullivan Statement about the use of electronic devices / examination aids: This is a closed-book examination. The use of camera devices, MP3 Players and headphones, or wireless access devices such as cell phones, Blackberries, etc., during the examination will not be allowed. nly nonprogrammable calculators and model kits are permitted for this examination. A hemical Data Sheet is provided. Instructions: This test consists of 18 multiple choice questions worth 2 marks each (total 36 marks) and 5 long answer questions (total 51 marks). The total value for the test is 87 marks. The exam has 20 pages make sure you have all 20 pages. All questions must be answered to obtain full marks. The answers to the multiple choice section must be entered on the optical score sheet. The time limit includes the time necessary to fill in the answers on the optical score sheet. The answers to the long answer questions must be written in the space provided on the question sheets AND all work must be shown. AT TE END F TE EXAMINATIN, AND IN TE PTIAL SRE SEET AND TE ENTIRE EXAM PAPER Failing to encode this Exam Booklet or your ptical Score Sheet correctly, for your name, ID and lecture section, will result in the loss of two marks 24
hem 201 Page 6 of 20 28 8) Rank the following molecules in order of increasing N N bond order: N 2 4, N 2 & N 3. a) N 2 4 < N 2 < N 3 b) N 2 < N 3 < N 2 4 c) N 2 < N 2 4 < N 3 d) N 2 4 < N 3 < N 2 e) N 3 < N 2 < N 2 4 9) Which of the following shows an acceptable VSEPR structure? i) ii) iii) iv) Si a) i only b) ii only c) iv only d) i and iv only e) None of the VSEPR structures above are correct. 28
hem 201 Page 7 of 20 29 10) Which of the following rows is/are possible for an element in the 2 nd row of the periodic table? VSEPR Molecular Shape Bond angles Energy diagram for hybridized central atom a) 180 b) <120 c) 120 d) All of the above e) None of the above 11) Which of the following correctly identifies the relationship between the molecules given? a) Same Molecule b) Geometric Isomers F F c) onstitutional Isomers N d) onformational Isomers e) None of the above 29
hem 201 Page 9 of 20 31 Vitamin B5 is used to synthesize and metabolize proteins, carbohydrates and fats. It is found in most foods, especially avocados. Use the structure given to answer Questions 14 to 17. N 14) Which of the following functional groups are present in vitamin B5? a) ester c) amine e) All are present b) amide d) ketone 15) Vitamin B5 can have. a) only constitutional isomers b) both optical and constitutional isomers c) both optical and conformational isomers d) both conformational and constitutional isomers e) optical, conformational and constitutional isomers. 16) Which of the following energy diagrams represent the hybridization of the oxygen atom of vitamin B5 indicated by the arrow? a) b) c) d) e) None of the above. 17) Which of the following statements is correct about vitamin B5? a) There are 4 -electrons in this molecule. b) ne can draw at least one other equivalent resonance structure. c) There are five sp 2 hybridized carbon atoms in vitamin B5. d) All of the above statements are correct. e) None of the above statements are correct. 31
hem 201 Page 10 of 20 32 18) onsider the following three compounds to answer the question below: N N N Which of the following is/are correct? i) all 3 compounds are constitutional isomers of each other. ii) all have the amine functional group. iii) structure 1 will have the highest boiling point iv) all have hydrogen bonding a) i only b) iii only c) i & ii only d) i & iii only e) iv only *******END F MULTIPLE IE QUESTIN SETIN******* 32
hem 201 Page 12 of 20 34 QUESTIN 20 VALUE 11.5 MARKS a) What is the condensed formula for 2-methylpentan-3-one? b) What is the IUPA name for the structure to the right? :.. c) What is the IUPA name for the structure shown to the right? d) Next to the structure in c) draw - and show arrow pushing to how it can be deprotonated to give 3 () - and 2. e) 3 () - displays resonance. Draw the resonance structures with arrows to show how they can interconvert. f) Draw the resulting resonance hybrid 34
hem 201 Page 13 of 20 35 g) Draw the best VSEPR structure for a non-polar molecule with the molecular formula 2 2 l 2. Give a constitutional isomer of the VSEPR you drew above that is polar. h) Identify and circle the chiral center in the molecule given to the right. l i) Draw the optical isomer for the molecule in h). 35
hem 201 Page 14 of 20 36 QUESTIN 21 VALUE 12 MARKS a) The condensed formula of the molecule shown below is b) Add all missing atoms and lone pairs to the structure to the right. l c) Fill the table below. If the name/value cannot be determined, write N/A. VSEPR electronpair geometry around this atom Molecular shape around this atom Atom 1 Atom 2 Atom 3 ybridization 36
hem 201 Page 18 of 20 40 QUESTIN 23 VALUE 12.5 MARKS Bromine triflouride, BF 3, will react with ammonia, N 3, to yield F 3 B N 3.. : : F :.... F B : F.. : + : N.. : : :.... F B : F + N BF 3 N 3 F 3 B N 3 F..: a) Draw curved arrow(s) on the reactants to show how they are interacting with one another to make the product. b) Draw the 3D VSEPR drawings for the reactants. c) BF 3 is a species. N 3 is a species. (polar / non-polar) (polar / non-polar) d) If 10.0 g of N 3 reacted with 34.0 g of BF 3 and produced 4.20 g of F 3 B N 3, what was the percent yield of this reaction? Show all your work. 40
hem 201 Page 19 of 20 41 e) N 3 can also react with 3 () 3 Draw the VSEPR structure f) Identify δ + and δ on your VSEPR structure above. g) 3 () 3 is a species. (polar / non-polar) h) List the intermolecular forces you see occurring between 3 () 3 and N 3. i) Draw the most favourable intermolecular interaction between 3 () 3 and N 3 if the resulting product formed from the interaction is: N *******END F WRITTEN ANSWER SETIN******* 41
hem 201 Page 1 of 21 5 TE UNIVERSITY F ALGARY FAULTY F SIENE EMISTRY 201 FALL 2016 FINAL EXAMINATIN Written Mark Written Mark Q19 Q23 Q20 Q24 Q21 Q25 Q22 DATE: Dec 19 th, 2016 TIME: 3 ours FIRST NAME: LAST NAME: Lecture Section: Please check one, then fill in ID # on next page! L01 MWF 1:00 pm Dr. V. Iosub L02 MWF 2:00 pm Dr. V. Iosub L03 TR 9:30 am Dr. E. Sullivan Statement about the use of electronic devices / examination aids: This is a closed-book examination. The use of camera devices, MP3 Players and headphones, or wireless access devices such as cell phones, Blackberries, etc., during the examination will not be allowed. nly nonprogrammable calculators and model kits are permitted for this examination. A hemical Data Sheet is provided. Instructions: This test consists of 18 multiple choice questions worth 2 marks each (total 36 marks) and 7 long answer questions (total 64 marks). The total value for the test is 100 marks. The exam has 21 pages make sure you have all 21 pages. All questions must be answered to obtain full marks. The answers to the multiple choice section must be entered on the optical score sheet. The time limit includes the time necessary to fill in the answers on the optical score sheet. The answers to the long answer questions must be written in the space provided on the question sheets AND all work must be shown. AT TE END F TE EXAMINATIN, AND IN TE PTIAL SRE SEET AND TE ENTIRE EXAM PAPER Failing to encode this Exam Booklet or your ptical Score Sheet correctly, for your name, ID and lecture section, will result in the loss of two marks 5
hem 201 Student ID#: Page 5 of 21 8 6) Which of the following VSEPR structures are drawn correctly? i) ii) iii) iv) a) All are drawn correctly b) nly i is correct c) nly i and iii are correct d) nly ii and iii are correct e) nly iii is correct 7) Which of the following are resonance structures of each other? 2 3 3 2 3 2 3 3 i ii iii iv a) i and ii only b) i and iii only c) ii and iv only d) iii and iv only e) All are resonance structures of each other 8) Which of the following statements is/are correct? a) All molecules can have equivalent resonance structures b) Electrons in resonance move through hybridized orbitals c) Electrons in resonance move through unhybridized p-orbitals d) Electrons in resonance only ever move between a lone pair and a multiple bond e) All of the above statements are correct 8
hem 201 Student ID#: Page 6 of 21 9 9) Rank the following molecules in order of increasing bond order:, 2 & 3. a) < 2 < 3 b) 2 < 3 < c) 2 < < 3 d) < 3 < 2 e) 3 < 2 < 10) Which of the following is/are valid VSEPR structures for 2 (l) 2 l? i) 2 l ii) l iii) l l l l iv) l l a) i only b) ii only c) iii only d) iv only e) None of the VSEPR structures above. 9
hem 201 Student ID#: Page 7 of 21 10 11) Which of the following rows is/are possible for an element in the 2 nd row of the periodic table? Structure Bond angles around central atom Energy diagram for hybridized central atom a) 180 b) 120 c) 109.5 d) All of the above e) None of the above 12) Which of the following correctly identifies the relationship between the molecules given? a) Same Molecule b) c) Geometric Isomers onstitutional Isomers l l l N 2 l ptical d) Isomers e) None of the above 10
hem 201 Student ID#: Page 8 of 21 11 Use the structure of Adrenaline to answer Questions 13 to 18. 13) Which of the following functional group(s) is/are present in Adrenaline? a) Alcohol c) Ester e) All are present b) Amide d) Aldehyde 14) Adrenaline can have... a) only constitutional isomers b) both optical and constitutional isomers c) both optical and conformational isomers d) both conformational and constitutional isomers e) optical, conformational and constitutional isomers. 15) Which of the following energy diagrams represent the hybridization of the nitrogen atom in Adrenaline? a) b) c) d) e) None of the above. 16) Which of the following statements is/are correct about Adrenaline? a) Adrenaline has one chiral centre. b) There are three pi-electrons in Adrenaline. c) The molecular shape around the nitrogen in Adrenaline is trigonal planar. d) All of the above. e) None of the above. 11
hem 201 Student ID#: Page 9 of 21 12 17) What types of orbitals do the lone pair(s) of the heteroatoms in the box occupy? a) N sp 3, sp 3 b) N sp 2, sp 2 c) N sp 3, sp 2 d) N sp 2, sp 3 e) N 2p, 2p 18) What term best describes the relationship between the two Adrenaline structures below: a) geometric isomers b) mirror images c) constitutional isomers d) conformational isomers e) optical isomers N N *******END F MULTIPLE IE QUESTIN SETIN******* 12
hem 201 Student ID#: Page 12 of 21 15 QUESTIN 21 VALUE 10 MARKS a) ircle and name two functional groups present in innamaldehyde. b) The geometry about the double bond not part of the benzene ring is. c) What is the strongest type of intermolecular forces present in innamaldehyde? d) The structure of Nicotine is shown to the right; what is the strongest type of intermolecular forces present in Nicotine? N N e) innamaldehyde is mixed with Nicotine, what is the strongest type of intermolecular force between these two species? Draw a picture of the interaction to rationalize your answer. 15
hem 201 Student ID#: Page 13 of 21 16 f) Between innamaldehyde and Nicotine, which do you feel would be more soluble in water? Briefly rationalize your answer. g) Looking above at the atoms labelled i-iii, fill in the table below. VSEPR electronpair geometry around this atom Molecular shape around this atom i ii iii ybridization 16
hem 201 Student ID#: Page 17 of 21 20 e) Use the diagram in b) to rank the following by increasing bond length: 2 2-, 2 & 2 2+ f) Potassium carbide, K 2 2, can react with water to form potassium hydroxide and ethyne. Draw the Lewis for each and show how the reaction occurs with curly arrows. g) What is the overall balanced equation for the reaction of K 2 2 and water? 20
hem 201 Student ID#: Page 18 of 21 21 QUESTIN 24 VALUE 6 MARKS Boric acid, B() 3, will react with water to yield () 3 B 2 as shown in the reaction below: B + B Boric Acid Product a) Draw curved arrow(s) on the reactants to show how they are interacting with one another to make the product. b) Draw the 3D VSEPR drawings for the reactants. c) The hybridization of B in B() 3 is. d) There are unhybridized p orbitals for B in B() 3. e) The hybridization of B in the product is. f) There are unhybridized p orbitals for B in the product. 21
hem 201 Student ID#: Page 19 of 21 22 QUESTIN 25 VALUE 9 MARKS a) omplete the following Table below, by filling each row. If something is not possible write N/A: Structure IUPA Name Draw a(n) onstitutional isomer i Ethyl propanoate ptical isomer ii onformational isomer iii 3 2 3 Geometric isomer iv b) If one or more of the isomers above are not possible please explain your reasoning for each. 22
hem 201 Student ID#: Page 20 of 21 23 c) nly one of the species above would react with Br 2, which would it be? d) l 2 has a boiling point of 34.04, Br 2 has a boiling point of 58.8 while I 2 has a boiling point of 184.3. Explain the differences in boiling points for l 2, Br 2 and I 2. *******END F WRITTEN ANSWER SETIN******* 23