DEPARTMENT OF CHEMISTRY AND CHEMICAL ORGANIC CHEMISTRY II 202-BZG-05 03

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1 DEPARTMENT OF CHEMISTRY AND CHEMICAL TECHNOLOGY ORGANIC CHEMISTRY II 202-BZG TEST 1 11 MARCH 2010 INSTRUCTOR: I. DIONNE PRINT YOUR NAME: Answers INSTRUCTIONS: Answer all questions in the space provided. 1. Duration of the exam is 75 minutes. 2. Answer all questions in the space provided. 3. Answer the questions in ink in order to preserve the right to grieve. 4. In order to obtain full credit for your answers, you must clearly show your work. 5. Calculators may not be shared. Programmable calculators are not permitted. 6. No books or extra paper are permitted. 7. Your attention is drawn to the College policy on cheating. This policy will be enforced.

2 PROBLEM 1 (a) The mass spectrum of an alkyl halide is shown below: (2 marks) i. What is the molecular mass of the alkyl halide? Answer: 108 ii. What halide is present? Answer: Br iii. On the spectrum, label the base peak and the molecular ion peak. Base peak M + (b) The mass spectrum of an unknown liquid shows a molecular ion peak at m/z = 78, with a relative intensity of The relative intensities of the isotopic peaks are as follows: (2 marks) m/z Relative intensity What is the molecular formula of this unknown? (Show your work) Answer: C 3 H 7 Cl m/z intensity % M M M M + 1: 3.35 / 1.1= carbons M + : M + 2 ratio 100 : 32.0, presence of Cl (3)(12) + (1)(35) = = 7 3 carbons, 1 chlorine, 7 hydrogens Page 2

3 (c) The mass spectra of two very stable cycloalkanes both show a molecular ion peak at m/z = 98. One spectrum shows a base peak at m/z = 69, the other shows a base peak at m/z = 83. Identify the cycloalkanes (draw structures). Show your work. (4 marks) Answers: mass of 98 98/12 = 8.17 probably 7 carbons = 29 loss CH 2 CH = 15 loss CH 3 stable radical cation m/z 69 stable radical cation m/z 83 69/12 = carbons 83/12 = carbons and loss CH 2 CH 3 and loss CH 3 PROBLEM 2 (3 marks) Answer all of the following questions: (a) In UV-Visible spectroscopy, the value of λ max increases as the extent of conjugation increases or decreases? Answer: increases (b) In IR spectroscopy, i. Which is higher in energy per photon, electromagnetic radiation with wavenumber 100 cm 1 or with wavenumber 2000 cm 1? Answer: 2000 cm 1 ii. Which would be expected to be more intense (stronger), the stretching vibration of a C=O bond or the stretching vibration of a C=C bond? Answer: C=O iii. Which will occur at a larger wavenumber, a C H stretch or a C H bend? Anwer: C H stretch iv Assuming that the force constants are the same, which will occur at a smaller wavenumber, a C O stretch or a C Cl stretch? Answer: C Cl stretch v. Which will occur at a larger wavenumber, a C N stretch or a C=N stretch? Answer: C=N stretch Page 3

4 PROBLEM 3 (6 marks) Assign three diagnostic bands (functional groups that are present) in the following IR spectra (write directly on the spectra). (a) C (sp 2 ) H C=C (b) O H C O (c) C C C (sp) H Page 4

5 PROBLEM 4 (a) Give reasonable structures for: (6 marks) i. A compound of the formula C 3 H 3 Cl 3 that shows only one signal in its 1 H and 13 C NMR spectra. Answer: ii A compound of the formula C 8 H 10 which shows the following absorptions in its proton NMR spectrum triplet, δ1.2, integral 7.8 cm Answer: quartet, δ2.6, integral 5.2 cm broad singlet, δ7.1, integral 13.0 cm (b) In the following molecule, which proton NMR signal would be the most downfield? (1 mark) Answer: C (c) How many signals would you expect to see in the 1 H NMR and 13 C NMR spectra of the following compound? (2 marks) Answer: 3 signals in the 1 H NMR 6 signals in the 13 C NMR Page 5

6 (d) For the compound below: (6 marks) a b c i. Give the spin-spin splitting (multiplicity) that would be observed for each of the protons sets in the 1 H NMR spectrum. Answer: H a, triplet H b quartet and H c singlet ii. Predict the approximate chemical shift (Shoolery) of each set of non-equivalent protons in the 1 H NMR spectrum. Answer: H a, 1.22 ppm H b 2.56 ppm and H c 4.76 ppm 0.6 ppm % ppm % ppm % PROBLEM 5 (8 marks) Write a structural formula for the compound whose molecular formula is C 7 H 14 O 2 that is consistent with the following spectroscopic data. Write directly onto the spectra. The more thoroughly your analysis is, the higher your grade will be. The answer itself is only part of the grade. Place your final structure in the box below. Answer: Page 6

7 no O H no C N no C C C O C = O e 5 different types of H a a b c d e c a doublet b multiplet c..doublet d..quartet (near oxygen) e triplet d a b O 1 O different carbons 1 / 8 2 / 3 3 / 6 4 / 15 5 / 8 / 40 Page 7

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