5. For the following molecules, draw the fragments based on the peaks listed. Consider the molecular ion and fragmentation patterns found in Ch. 13 of your lab textbook. m/z 162, 120, 105, 77
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- Model 3: Ionization and Fragmentation Most mass spectrometers accelerate a molecule by first turning it into an ion, then using an electric field to accelerate it toward the detector. During standard ionization, a molecule loses one electron, the electron that is easiest to remove. The following is a hierarchy of electrons from easiest to hardest to remove: Electron in a lone pair (easiest) Electron that is part of a double bond (pi bond) Electron in a single bond (hardest) Knocking off an electron to make a +1 ion can be a harsh process. This harsh treatment often results in a broken bond, generating two smaller pieces, a +1 ion and a neutral fragment. (Note that only the ion is accelerated and detected.) ● 7. ● Critical Thinking Questions 6. If acetone is ionized, which electron is most likely to be knocked off? Replace this electron with a + (to indicate the missing electron) on the structure of acetone → The ion you drew above is called the "molecular ion" of acetone. It is…1. Which one of the given compounds is consistent with the mass spectrum below? 100 40 20 10 20 25 30 35 40 5o 55 45 60 65 70 75 m/z Courtesy of SDBS: National Institute of Advanced Industrial Science and Technology A. CH,CH,CH(CH,), В. CH,CHOHCH,CH, C. CH,CH,OCH,CH, D. CH,CH,NHCH,CH, E. CH,CH,CH,CH, Relative htensityD10) 1.Give an advantage and a disadvantage of the spectra obtained from an electron impact (EI) mass spectrometer? 2. What is the base peak in an electron impact mass spectrum? Name one property of the positive fragment that gives rise to this signal? 3. Explain why the mass-to-charge ratio of ions in the EI mass spectrometer are usually equal to the masses of the ions
- For each of the following molecules, draw the most likely molecular ions (always a radical cation) that you would expect to be formed in an EI-MS experiment. For each case, calculate the m/z value for the molecular ion on the most abundant isotopomer. (C = 12, N = 14, O = 16, Cl = 35, Br = 79)Show a possible stepwise synthesis of 2, 3-dichlerapentane starting with ethanol and propanol as the only sources of carbon atoms and any other inorganic reagents, solvents and laboratory equipment. Name the type of reaction that is occurring in each step of the synthesis. а. A mass spectrum was measured of 2, 3-dichloropentane, At what m/z values would the molecular ion peak and the isotope peaks appear? What would be the relative abundances of these peaks? b. a.27. The rule you generated in Question 14b for finding the [M] peak on the mass spectrum of an unknown molecule does not work very well if there is a Br or Cl in the molecule. Shown below are spectra of various compounds containing one Br or Cl. a. Find the [M] and [M+2]* peak on each spectrum. Relative Intensity 100- Relative Intensity 80- 60 20- 0-mmm 100- 80 60- 40 18--8163 20- 25 HS-NU-2127 0-forttitor 10 20 b. 30 50 40 50 Br pretztenyeregtelefongum 75 m/z 60 m/z Bri 70 100 (2) one Br atom. 125 effleyttim 90 80 ||||||| 100 110 Relative Intensity 100 Relative Intensity 80 60- 40 20 0-m 100- 80 60 40 20 15-MM-0968 0- spatepragning 25 115--1439 25 50 50 75 NH₂ 100 m/z mn||| 75 m/z 125 100 150 125 Write a rule for quickly identifying from a mass spectrum if an unknown molecule has... (1) one Cl atom. Note: The mass spectrum of a molecule with more than one Cl or Br can be quite complex, so we will limit cases to one Cl or Br. Write a new rule for finding the [M]* peak that takes into…
- 4. The following is the mass spectrum of tert-butylbenzene. a) label the molecular ion peak on the spectrum b) label the base peak on the spectrum c) draw the fragmentation of the molecular ion to produce the base peak fragmentation 100 119 80 60 40 134 20 0.0+ 0.0 40 80 120 160 m/z Rel. IntensityGuide Question: 1. Draw the molecular structure of aspirin. Identify the molecular ion peak and base peak based on the mass spectrum of aspirin. 2. Analyze the mass spectrum of aspirin. Identify the structure of the fragment ions for the three tallest peaks. 3. Assign the following M+ peak (molecular formula). Write down the C, H, O atoms (note: separated by a comma). 180 m/z 138 m/z 120 m/z 92 m/z 64 m/z 43 m/z2. The mass spectrum of a hydrocarbon is shown below. Use the Rule of 13 to determine a molecular formula and use the formula to calculate units of unsaturation. Assume that the peak at m/z 120 is the molecular ion. What are possible structures for this compound? 100 80 60- 40 20 10 20 30 40 50 60 70 80 90 100 110 120 m/z Relative Intensity
- 2) One of the rules in determining molecular formulas from mass spectroscopy is the nitrogen rule. a. Below are four different molecules containing nitrogen. Write the molecular formula and then determine what the expected m/z is. Molecular formula: m/z: OH NH2 NH2 ∞eç NH HN. NH₂ NH₂ b. What pattern do you notice relating the number of nitrogens to the mass of each molecule? Based on this pattern, write the nitrogen rule in your own words.6) Which compound would show major fragment ions at both m/z = 73 and m/z = 59? Bubble in your answer completely. OH ОН ОН ОН7. The ir and MS for a compound are shown below. Identify the compound. Clearly show your reasoning. b. 100 83 41 162||164 20 40 60 80 100 120 140 160