Organic Chemistry 6th Edition Brown Foote Iverson Test bank

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Organic Chemistry 6th Edition Brown Foote Iverson Test bank

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CHAPTER 14MASS SPECTROMETRY
Student: ___________________________________________________________________________
1. What is the principle that allows us to use mass spectrometry to determine the molecular weight of a compound? A. higher molecular weight compounds are less volatileB. higher molecular weight compounds are more denseC. a beam of higher molecular weight cations is deflected less by a magnetic fieldD. ions with higher molecular weight absorb higher frequencies of light
 
2. In mass spectrometry, which of the following phrases is shortened to the acronym FAB? A. flight averaged bumpingB. fast atom bombardmentC. fragmented atom beamD. flying atom bashing
 
3. In mass spectrometry, which of the following phrases is shortened to the acronym EI? A. electron injectionB. electron impactC. energy initiatedD. energy insertion
 
4. In mass spectrometry, which of the following phrases is shortened to the acronym MALDI? A. mass analysis by light-detected ionsB. matrix assisted laser desorption ionizationC. many atom loss-detecting ionizationD. molecular and light detecting instrument
 
5. What is the x-axis of a mass spectrum? A. massB. mass/energyC. mass/chargeD. charge
 
6. What is the y-axis of a mass spectrum? A. massB. energyC. abundanceD. field strength
 
7. Which of the following is the definition of the base peak of a mass spectrum? A. the peak corresponding to the most abundant ionB. the peak corresponding to the ion with lowest m/eC. the peak corresponding to the molecular ion peakD. the peak corresponding to the ion arising to loss of a proton from the molecular ion
 
8. Which of the following corresponds to the molecular ion in EI mass spectrometry? A. the most abundant ionB. the ion with the smallest m/eC. the ion formed by removal of an electron from the moleculeD. any ion formed by fragmentation of the molecule
 
9. What are products of the collision between high energy electrons and methane? A. CH4- + 2 e-B. CH3- + HC. CH4+ + 2 e-D. CH3 + H+ + 2 e-
 
10. Which of the following sets of molecular ions does an alkyl bromide possess? A. two molecular ions in a 2:1 ratio separated by two mass unitsB. two molecular ions in a 1:1 ratio separated by two mass unitsC. three molecular ions in a 1:2:1 ratio separated by two mass unitsD. two molecular ions in a 3:1 ratio separated by two mass units
 
11. Which of the following sets of molecular ions does an alkyl chloride possess? A. two molecular ions in a 2:1 ratio separated by two mass unitsB. two molecular ions in a 1:1 ratio separated by two mass unitsC. three molecular ions in a 1:2:1 ratio separated by two mass unitsD. two molecular ions in a 3:1 ratio separated by two mass units
 
12. Which of the following sets of molecular ions does a dibromoalkane possess? A. two molecular ions in a 2:1 ratio separated by two mass unitsB. two molecular ions in a 1:1 ratio separated by two mass unitsC. three molecular ions in a 1:2:1 ratio, separated by two mass unitsD. two molecular ions in a 3:1 ratio separated by two mass units
 
13. Which of the following is most consistent with a molecule having a molecular ion with m/e of 77? A. the molecule contains bromineB. the molecule contains nitrogenC. the molecule is an alcoholD. the molecule is a hydrocarbon
 
14. How many carbon atoms are present in a molecule which gives an M+1 peak that is 5.74% of the intensity of the molecular ion? A. 5B. 6C. 11D. 12
 
15. How many carbon atoms are present in a molecule which gives an M+1 peak that is 11.48% of the intensity of the molecular ion? A. 5B. 6C. 11D. 12
 
16. Which of the molecules gives rise to a molecular ion with an odd value of m/e? A. C6H12Cl2B. C7H10N2C. C8H13ND. C8H14Br2
 
17. Which of the molecules gives rise to a molecular ion with an odd value of m/e? A. C6H12O2B. C7H10ClNC. C8H18N2D. C8H12
 
18. What are the most common products of the fragmentation of a molecular ion? A. two radicalsB. an anion and a cationC. a radical and a cationD. two cations
 
19. Which of the following is not prominent in the mass spectrum of 2-methyl-2-butanol? A. M 29B. M 18C. M 15D. M 12
 
20. Which of the following bonds of the octane radical cation is least subject to fragmentation? A. iB. iiC. iiiD. iv
 
21. Which of the following gives rise to a prominent M 18 peak in the mass spectrum? A. hexaneB. 1-chloropentaneC. 1-pentanolD. 3-methylpentane
 
22. Which of the following gives rise to a prominent M 15 peak in the mass spectrum? A. hexaneB. 1-chloropentaneC. 1-pentanolD. 3-methylpentane
 
23. Which of the following gives rise to a prominent peak in the mass spectrum at m/z of 39? A. 1-octyneB. 4-octyneC. 5-methyl-3-octyneD. 2,2-dimethyl-3-heptyne
 
24. Which of the following does not give rise to a prominent M 41 peak in the mass spectrum? A. 1-hexeneB. 3-methyl-1-hexeneC. 4-methyl-1-hexeneD. 5-methyl-1-hexene
 
25. Which of the following is not prominent in the mass spectrum of 2-methyl-2-butanol? A. M 15B. M 18C. M 21D. M 29
 
26. Which of the following alcohols does not give a prominent M 15 ion? A. isopropyl alcoholB. tert-butyl alcoholC. 2-hexanolD. 3-pentanol
 
27. Which of the following gives rise to a prominent M 18 peak in the mass spectrum? A. cyclohexaneB. cyclohexeneC. 1-chlorocyclohexaneD. cyclohexanol
 
28. Which of the following gives rise to a prominent M 15 peak in the mass spectrum? A. cyclopentaneB. cyclopenteneC. cyclopentanolD. methylcyclopentane
 
29. Which of the following gives rise to a prominent peak in the mass spectrum with m/z of 41? A. 1-hexeneB. 2-hexyneC. 3-hexanolD. 2-chlorohexane
 
30. Which of the following gives rise to a prominent peak in the mass spectrum with m/z of 43? A. 1-hexanolB. 2-hexanolC. hexanalD. hexanoic acid
 
31. Which of the following gives rise to a prominent peak in the mass spectrum with m/z of 45? A. 1-hexanolB. 2-hexanolC. hexanalD. hexanoic acid
 
32. Which of the following gives rise to a prominent peak in the mass spectrum with m/z of 60? A. 1-hexanolB. 2-hexanolC. hexanalD. hexanoic acid
 
33. Which of the following gives rise to a prominent peak in the mass spectrum with m/z of M 31? A. 2-methylhexanoic acidB. methyl hexanoateC. ethyl hexanoateD. hexanoic acid
 
34. Which of the following gives rise to a prominent peak in the mass spectrum with m/z of 91? A. 1-octeneB. 1-hexanamine, CH3CH2CH2CH2CH2CH2NH2C. benzeneD. ethylbenzene
 
35. Which of the following gives rise to a prominent peak in the mass spectrum with m/z of 30? A. 1-hexanamine, CH3CH2CH2CH2CH2CH2NH2B. 1,1-dimethyl-1-butanamine, CH3CH2CH2C(CH3)2NH2C. 1-hexanolD. hexanal
 
36. What is the most likely molecular formula of a compound that has a molecular ion in the EI mass spectrum with m/z of 97 and an M+1 peak that is 6.6% of the intensity of the molecular ion peak? 
 
 
 
 
 
37. What is the most likely moleuclar formula of a compound (that contains only C, H and O) which has a molecular ion in the EI mass spectrum with m/z of 104 and an M+1 peak that is 5.5% of the intensity of the molecular ion peak? 
 
 
 
 
 
38. What is the most likely molecular formula of a compound that has a molecular ion in the EI mass spectrum with m/z of 136, with a M+1 and M+2 peaks that are 4.4% and 49% of the intensity of the molecular ion peak, respectively. 
 
 
 
 
 
39. What is the most likely moleuclar formula of a compound that has a molecular ion in the EI mass spectrum with m/z of 120, with a M+1 and M+2 peaks that are 6.6% and 24% of the intensity of the molecular ion peak, respectively. 
 
 
 
 
 
40. Provide the mass of the three most prominant fragment peaks that are observed in the EI mass spectrum of 2-hexanone, CH3CH2CH2CH2COCH3 (molecular ion m/z = 100) and describe the processes that lead to each of these fragments. 
 
 
 
 
 
41. Provide the mass of the three most prominant fragment peaks that are observed in the EI mass spectrum of methyl pentanoate, CH3CH2CH2CH2CO2CH3 (molecular ion m/z = 116) and describe the processes that lead to each of these fragments. 
 
 
 
 
 
42. Which C5H12O compound give the following EI mass spectrum? 
 
 
 
 
 
43. Which C5H12O compound give the following EI mass spectrum? 
 
 
 
 
 
44. Which C6H12O carbonyl-containing compound shows a molecular ion peak at m/z 100 and significant fragment peaks at m/z 85, 58, 57, 43 and 42 in the EI mass spectrum? 
 
 
 
 
 
45. Which C6H12O carbonyl-containing compound shows a molecular ion peak at m/z 100 and significant fragment peaks at m/z 71, 58, 57, 43 and 29 in the EI mass spectrum? 
 
 
 
 
 

CHAPTER 14MASS SPECTROMETRY Key 
1. What is the principle that allows us to use mass spectrometry to determine the molecular weight of a compound? A. higher molecular weight compounds are less volatileB. higher molecular weight compounds are more denseC. a beam of higher molecular weight cations is deflected less by a magnetic fieldD. ions with higher molecular weight absorb higher frequencies of light
 
2. In mass spectrometry, which of the following phrases is shortened to the acronym FAB? A. flight averaged bumpingB. fast atom bombardmentC. fragmented atom beamD. flying atom bashing
 
3. In mass spectrometry, which of the following phrases is shortened to the acronym EI? A. electron injectionB. electron impactC. energy initiatedD. energy insertion
 
4. In mass spectrometry, which of the following phrases is shortened to the acronym MALDI? A. mass analysis by light-detected ionsB. matrix assisted laser desorption ionizationC. many atom loss-detecting ionizationD. molecular and light detecting instrument
 
5. What is the x-axis of a mass spectrum? A. massB. mass/energyC. mass/chargeD. charge
 
6. What is the y-axis of a mass spectrum? A. massB. energyC. abundanceD. field strength
 
7. Which of the following is the definition of the base peak of a mass spectrum? A. the peak corresponding to the most abundant ionB. the peak corresponding to the ion with lowest m/eC. the peak corresponding to the molecular ion peakD. the peak corresponding to the ion arising to loss of a proton from the molecular ion
 
8. Which of the following corresponds to the molecular ion in EI mass spectrometry? A. the most abundant ionB. the ion with the smallest m/eC. the ion formed by removal of an electron from the moleculeD. any ion formed by fragmentation of the molecule
 
9. What are products of the collision between high energy electrons and methane? A. CH4- + 2 e-B. CH3- + HC. CH4+ + 2 e-D. CH3 + H+ + 2 e-
 
10. Which of the following sets of molecular ions does an alkyl bromide possess? A. two molecular ions in a 2:1 ratio separated by two mass unitsB. two molecular ions in a 1:1 ratio separated by two mass unitsC. three molecular ions in a 1:2:1 ratio separated by two mass unitsD. two molecular ions in a 3:1 ratio separated by two mass units
 
11. Which of the following sets of molecular ions does an alkyl chloride possess? A. two molecular ions in a 2:1 ratio separated by two mass unitsB. two molecular ions in a 1:1 ratio separated by two mass unitsC. three molecular ions in a 1:2:1 ratio separated by two mass unitsD. two molecular ions in a 3:1 ratio separated by two mass units
 
12. Which of the following sets of molecular ions does a dibromoalkane possess? A. two molecular ions in a 2:1 ratio separated by two mass unitsB. two molecular ions in a 1:1 ratio separated by two mass unitsC. three molecular ions in a 1:2:1 ratio, separated by two mass unitsD. two molecular ions in a 3:1 ratio separated by two mass units
 
13. Which of the following is most consistent with a molecule having a molecular ion with m/e of 77? A. the molecule contains bromineB. the molecule contains nitrogenC. the molecule is an alcoholD. the molecule is a hydrocarbon
 
14. How many carbon atoms are present in a molecule which gives an M+1 peak that is 5.74% of the intensity of the molecular ion? A. 5B. 6C. 11D. 12
 
15. How many carbon atoms are present in a molecule which gives an M+1 peak that is 11.48% of the intensity of the molecular ion? A. 5B. 6C. 11D. 12
 
16. Which of the molecules gives rise to a molecular ion with an odd value of m/e? A. C6H12Cl2B. C7H10N2C. C8H13ND. C8H14Br2
 
17. Which of the molecules gives rise to a molecular ion with an odd value of m/e? A. C6H12O2B. C7H10ClNC. C8H18N2D. C8H12
 
18. What are the most common products of the fragmentation of a molecular ion? A. two radicalsB. an anion and a cationC. a radical and a cationD. two cations
 
19. Which of the following is not prominent in the mass spectrum of 2-methyl-2-butanol? A. M 29B. M 18C. M 15D. M 12
 
20. Which of the following bonds of the octane radical cation is least subject to fragmentation? A. iB. iiC. iiiD. iv
 
21. Which of the following gives rise to a prominent M 18 peak in the mass spectrum? A. hexaneB. 1-chloropentaneC. 1-pentanolD. 3-methylpentane
 
22. Which of the following gives rise to a prominent M 15 peak in the mass spectrum? A. hexaneB. 1-chloropentaneC. 1-pentanolD. 3-methylpentane
 
23. Which of the following gives rise to a prominent peak in the mass spectrum at m/z of 39? A. 1-octyneB. 4-octyneC. 5-methyl-3-octyneD. 2,2-dimethyl-3-heptyne
 
24. Which of the following does not give rise to a prominent M 41 peak in the mass spectrum? A. 1-hexeneB. 3-methyl-1-hexeneC. 4-methyl-1-hexeneD. 5-methyl-1-hexene
 
25. Which of the following is not prominent in the mass spectrum of 2-methyl-2-butanol? A. M 15B. M 18C. M 21D. M 29
 
26. Which of the following alcohols does not give a prominent M 15 ion? A. isopropyl alcoholB. tert-butyl alcoholC. 2-hexanolD. 3-pentanol
 
27. Which of the following gives rise to a prominent M 18 peak in the mass spectrum? A. cyclohexaneB. cyclohexeneC. 1-chlorocyclohexaneD. cyclohexanol
 
28. Which of the following gives rise to a prominent M 15 peak in the mass spectrum? A. cyclopentaneB. cyclopenteneC. cyclopentanolD. methylcyclopentane
 
29. Which of the following gives rise to a prominent peak in the mass spectrum with m/z of 41? A. 1-hexeneB. 2-hexyneC. 3-hexanolD. 2-chlorohexane
 
30. Which of the following gives rise to a prominent peak in the mass spectrum with m/z of 43? A. 1-hexanolB. 2-hexanolC. hexanalD. hexanoic acid
 
31. Which of the following gives rise to a prominent peak in the mass spectrum with m/z of 45? A. 1-hexanolB. 2-hexanolC. hexanalD. hexanoic acid
 
32. Which of the following gives rise to a prominent peak in the mass spectrum with m/z of 60? A. 1-hexanolB. 2-hexanolC. hexanalD. hexanoic acid
 
33. Which of the following gives rise to a prominent peak in the mass spectrum with m/z of M 31? A. 2-methylhexanoic acidB. methyl hexanoateC. ethyl hexanoateD. hexanoic acid
 
34. Which of the following gives rise to a prominent peak in the mass spectrum with m/z of 91? A. 1-octeneB. 1-hexanamine, CH3CH2CH2CH2CH2CH2NH2C. benzeneD. ethylbenzene
 
35. Which of the following gives rise to a prominent peak in the mass spectrum with m/z of 30? A. 1-hexanamine, CH3CH2CH2CH2CH2CH2NH2B. 1,1-dimethyl-1-butanamine, CH3CH2CH2C(CH3)2NH2C. 1-hexanolD. hexanal
 
36. What is the most likely molecular formula of a compound that has a molecular ion in the EI mass spectrum with m/z of 97 and an M+1 peak that is 6.6% of the intensity of the molecular ion peak? 
C6H11N
 
37. What is the most likely moleuclar formula of a compound (that contains only C, H and O) which has a molecular ion in the EI mass spectrum with m/z of 104 and an M+1 peak that is 5.5% of the intensity of the molecular ion peak? 
C5H12O2
 
38. What is the most likely molecular formula of a compound that has a molecular ion in the EI mass spectrum with m/z of 136, with a M+1 and M+2 peaks that are 4.4% and 49% of the intensity of the molecular ion peak, respectively. 
C4H9Br
 
39. What is the most likely moleuclar formula of a compound that has a molecular ion in the EI mass spectrum with m/z of 120, with a M+1 and M+2 peaks that are 6.6% and 24% of the intensity of the molecular ion peak, respectively. 
C6H13Cl
 
40. Provide the mass of the three most prominant fragment peaks that are observed in the EI mass spectrum of 2-hexanone, CH3CH2CH2CH2COCH3 (molecular ion m/z = 100) and describe the processes that lead to each of these fragments. 
85: loss of CH3 (15) by a-cleavage72: loss of CH2=CH2 (28) by McLaferty rearrangement43: loss of C4H9 (57) by a-cleavage
 
41. Provide the mass of the three most prominant fragment peaks that are observed in the EI mass spectrum of methyl pentanoate, CH3CH2CH2CH2CO2CH3 (molecular ion m/z = 116) and describe the processes that lead to each of these fragments. 
88: loss of CH2=CH2 (28) by McLaferty rearrangement85: loss of CH3O (31) by a-cleavage59: loss of C4H9 (57) by a-cleavage
 
42. Which C5H12O compound give the following EI mass spectrum? 
2-pentanol
 
43. Which C5H12O compound give the following EI mass spectrum? 
2-methyl-2-butanol
 
44. Which C6H12O carbonyl-containing compound shows a molecular ion peak at m/z 100 and significant fragment peaks at m/z 85, 58, 57, 43 and 42 in the EI mass spectrum? 
4-methyl-2-pentanone
 
45. Which C6H12O carbonyl-containing compound shows a molecular ion peak at m/z 100 and significant fragment peaks at m/z 71, 58, 57, 43 and 29 in the EI mass spectrum? 
2-methylpentanal
 

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