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html Multiple choice questions Try the following multiple choice questions to test your knowledge of this chapter. For each question there is one correct answer. The periodic table, physical constants and relative atomic masses needed for these problems are given on the inside covers of Chemistry, fourth edition by C.E. Housecroft and E.C. Constable. Once you have answered the questions, click on 'Submit Answers for Grading' to get your results. If your lecturer has requested that you send your results, please complete the routing information found at the bottom of your graded page and then click on the 'E-Mail Results' button. Please do not forward your results unless your lecturer has specifically requested that you do so. This activity contains 18 questions.

For a nucleus with nuclear spin quantum number I = , what are the values of mI? +, 0 +, +1 0, +1 +,

Which list below gives only spin active nuclei?


1

H, 13C, 19F H, 2H, 12C H, 12C, 19F H, 12C, 19F

Which carbon environment and 13C chemical shift range are correctly matched in the pairs below? aliphatic group RCH2X; +100 to +150 ppm alkene R2C=CR2; +50 to +80 ppm nitrile CN; +50 to +100 ppm ketone R2C=O; +190 to +230 ppm

What do you expect to observe in the 1H NMR spectrum of chloroethane CH3CH2Cl? A doublet and a triplet. A doublet and a quartet. A triplet and a quartet. Two doublets.

What signals do you expect to see in the 1H NMR spectrum of 1,1-dichloroethane CH3CHCl2? A singlet and a doublet. A doublet and a quartet. A doublet and a triplet. A singlet and a quartet.

How many signals do you expect to see in the 1H NMR spectra of 2-bromopropane (CH3)2CHBr and 1-

bromopropane CH3CH2CH2Br? 1-Bromopropane: 3; 2-bromopropane: 2. 1-Bromopropane: 2; 2-bromopropane: 2. 1-Bromopropane: 3; 2-bromopropane: 3. 1-Bromopropane: 2; 2-bromopropane: 3.

The 13C NMR spectrum of a compound A contains two signals and in the 1H NMR spectrum there is a singlet. Which compound is consistent with these data? Ethanol. Acetone. Dichloromethane. Bromoethane.

The 1H NMR spectrum of a compound B shows a doublet and a septet. Which of the following statements is true? The spectroscopic data are consistent with B containing a propyl (CH3CH2CH2) group. The spectroscopic data are consistent with B being (CH3)2CHCl. The spectroscopic data are consistent with B containing a CH3CH2 group. The spectroscopic data are consistent with B being (CH3)2CCl2.

A 1H NMR spectrum of compound C contains a singlet, a triplet and a quartet. Which of the following compounds might C be? CH3CHClCHClCH3 CH3CCl2CH2CH3 CH3CH2CH2CHCl2 CH3CH2CHClCHCl2

The 13C NMR spectrum of a compound D shows three signals, all in the region +10 to +60 ppm. Based on these data, which conclusion is incorrect? Compound D does not contain a ketone functional group. Compound D is not a carboxylic acid. Compound D is likely to contain aliphatic C atoms. Compound D contains three C atoms.

Which of the following compounds contains one or more protons that could undergo exchange with protons in water? CH3OH CH3Br (CH3)2O (CH3)3N

A 1H NMR spectrum of CH3CHBr2 shows two signals. What are the multiplicities and assignments of these signals? A quartet assigned to the CH3 group and a doublet assigned to the CH group. A doublet assigned to the CH3 group and a quartet assigned to the CH group. A triplet assigned to the CH3 group and a singlet assigned to the CH group. Two singlets, one assigned to each of the CH3 and CH groups.

In the IR spectrum of a compound X, there is a strong absorption at 1718 cm1 in addition to bands at 2978 and 2940 cm1 and bands below 1500 cm1. The 1H NMR spectrum contains two signals: a quartet and a triplet with relative integrals of 2 : 3. Of the following compounds, which is X most likely to be? CH3CH2OCH2CH3 CH3CH2OH CH3CH2CO2H CH3CH2COCH2CH3

A compound A analyses as containing 69.52 % C and 10.21 % H. Among other absorptions, the IR spectrum of A contains a sharp band at 2250 cm1. The 1H NMR spectrum (recorded in CDCl3), two triplets ( 2.34, 1.08 ppm) and a sextet ( 1.70 ppm) are observed. Compound A is: CH3CH2CH2CHO CH3CH2CH2NH2 CH3CH2CH2CN (CH3)2CHCN

The 13C{1H} NMR spectrum of a CDCl3 solution of an ether Z exhibits signals at 71.9 and 59.0 ppm, while in the 1H NMR spectrum there are two singlets at 3.55 and 3.39 ppm (relative integrals 3 : 2). Which of the following compounds is Z most likely to be? CH3OCH2CH2OCH3 CH3CH2OCH2OCH2CH3 CH3OCH2OCH3 CH3CH2OCH2CH3

Vicinal coupling is: coupling between 1H nuclei attached to the same C atom. coupling between 1H nuclei attached to adjacent C atoms. coupling between 1H nuclei in an alkene. coupling between 1H nuclei in an alkane.

Which statement corresponds to the case where the chemical shift difference between two coupling protons is less than 5-times the coupling constant? A first-order spectrum is expected. An AX pattern is observed. An AB pattern is observed.

An undistorted binomial splitting pattern is expected.

A 1H-1H coupling constant for a doublet in a compound X is measured as 5.0 Hz on a 500 MHz NMR spectrometer. Which of the following statements is incorrect? The difference for the two components of this doublet depends on the field strength of the spectrometer. For this doublet, the coupling constant is 5.0 Hz when the spectrum of X is recorded on a 250 MHz NMR spectrometer. The difference for the two components of this doublet is 0.05 ppm when measured on a 100 MHz spectrometer. For this doublet, the coupling constant measured in Hz depends on the field strength of the spectrometer.

1.

For a nucleus with nuclear spin quantum number I = , what are the values of mI? Your Answer: +,

2.

Which list below gives only spin active nuclei?


1 Your Answer: H, 13

C,

19

3.

Which carbon environment and

13

C chemical shift range are correctly matched in the pairs below?

Your Answer: aliphatic group RCH2X; +100 to +150 ppm Correct Answer: ketone R2C=O; +190 to +230 ppm

4.

What do you expect to observe in the 1H NMR spectrum of chloroethane CH3CH2Cl? Your Answer: A doublet and a triplet. Correct Answer: A triplet and a quartet.

5.

What signals do you expect to see in the 1H NMR spectrum of 1,1-dichloroethane CH3CHCl2? Your Answer: A doublet and a quartet.

6.

How many signals do you expect to see in the 1H NMR spectra of 2-bromopropane (CH3)2CHBr and 1bromopropane CH3CH2CH2Br? Your Answer: 1-Bromopropane: 2; 2-bromopropane: 2.

Correct Answer: 1-Bromopropane: 3; 2-bromopropane: 2.

7.

The 13C NMR spectrum of a compound A contains two signals and in the 1H NMR spectrum there is a singlet. Which compound is consistent with these data? Your Answer: Acetone.

8.

The 1H NMR spectrum of a compound B shows a doublet and a septet. Which of the following statements is true? Your Answer: The spectroscopic data are consistent with B being (CH3)2CHCl.

9.

A 1H NMR spectrum of compound C contains a singlet, a triplet and a quartet. Which of the following compounds might C be? Your Answer: CH3CH2CH2CHCl2 Correct Answer: CH3CCl2CH2CH3

10.

The 13C NMR spectrum of a compound D shows three signals, all in the region +10 to +60 ppm. Based on these data, which conclusion is incorrect? Your Answer: Compound D is likely to contain aliphatic C atoms. Correct Answer: Compound D contains three C atoms.

11.

Which of the following compounds contains one or more protons that could undergo exchange with protons in water? Your Answer: (CH3)2O Correct Answer: CH3OH

12.

A 1H NMR spectrum of CH3CHBr2 shows two signals. What are the multiplicities and assignments of these signals? Your Answer: A triplet assigned to the CH3 group and a singlet assigned to the CH group. Correct Answer: A doublet assigned to the CH3 group and a quartet assigned to the CH group.

13.

In the IR spectrum of a compound X, there is a strong absorption at 1718 cm1 in addition to bands at 2978 and 2940 cm1 and bands below 1500 cm1. The 1H NMR spectrum contains two signals: a quartet and a triplet with relative integrals of 2 : 3. Of the following compounds, which is X most likely to be? Your Answer: CH3CH2OH Correct Answer: CH3CH2COCH2CH3

14.

A compound A analyses as containing 69.52 % C and 10.21 % H. Among other absorptions, the IR spectrum of A contains a sharp band at 2250 cm1. The 1H NMR spectrum (recorded in CDCl3), two triplets ( 2.34, 1.08 ppm) and a sextet ( 1.70 ppm) are observed. Compound A is: Your Answer: CH3CH2CH2CHO Correct Answer: CH3CH2CH2CN

15.

The 13C{1H} NMR spectrum of a CDCl3 solution of an ether Z exhibits signals at 71.9 and 59.0 ppm, while in the 1H NMR spectrum there are two singlets at 3.55 and 3.39 ppm (relative integrals 3 : 2). Which of the following compounds is Z most likely to be? Your Answer: CH3CH2OCH2OCH2CH3 Correct Answer: CH3OCH2CH2OCH3

16.

Vicinal coupling is:


1 Your Answer: coupling between H nuclei attached to adjacent C atoms.

17.

Which statement corresponds to the case where the chemical shift difference between two coupling protons is less than 5-times the coupling constant? Your Answer: An AX pattern is observed. Correct Answer: An AB pattern is observed.

18.

A 1H-1H coupling constant for a doublet in a compound X is measured as 5.0 Hz on a 500 MHz NMR spectrometer. Which of the following statements isincorrect? Your Answer: For this doublet, the coupling constant is 5.0 Hz when the spectrum of X is recorded on a 250 MHz NMR spectrometer. Correct Answer: For this doublet, the coupling constant measured in Hz depends on the field strength of the spectrometer.

http://chemistry.boisestate.edu/people/richardbanks/organic/mc/vol3/mcquestions317c.htm

Organic Chemistry Practice Multiple Choice Question Set 3


1. Which of the following nuclei will have a magnetic moment?

2. How many absorptions will the following compound have in its carbon NMR spectrum?

(a) (b) (c) (d)

3 4 5 6

3. The CMR spectrum of an unknown compound shows 6 absorptions and the PMR spectrum shows 5 absorptions. Which of the following compounds is the unknown compound?

4. The CMR spectrum of an unknown compound shows 4 absorptions and the PMR spectrum shows 4 absorptions. Which of the following compounds is the unknown compound?

5. What is the multiplicity expected in the hydrogen NMR spectrum for the hydrogen atoms marked by a "star" in the following compound?

(a) (b) (c) (d)

singlet triplet quartet heptet

6. Which of the following compounds best fits the PMR spectrum shown below. The table shows the chemical shift for groups attached to a bromine atom or a cyano group measured to the center of the multiplet.

7. Which of the following alkyl groups would show the multiplet pattern depicted in the diagram?

Copyright August 2000 by Richard C. Banks...all rights reserved.

1a - You are correct! Nuclei that have an odd atomic number, odd atomic mass or both will have magnetic moments. 1b -This answer is not correct. Nuclei that have an odd atomic number, odd atomic mass or both will have magnetic moments. This nucleus has an even atomic number and an even atomic mass. 1c This answer is not correct. Nuclei that have an odd atomic number, odd atomic mass or both will have magnetic moments. This nucleus has an even atomic number and an even atomic mass. 1d This answer is not correct. Nuclei that have an odd atomic number, odd atomic mass or both will have magnetic moments. This nucleus has an even atomic number and an even atomic mass.

2a -This answer is not correct. Remember that each unique position of an atom will have a unique absorption. Think about the geometry of the compound and the neighboring atoms. 2b -This answer is not correct. Perhaps you thought that all of the methyl groups were equivalent in the structure. Remember that each unique position of an atom will have a unique absorption. Think about the geometry of the compound and the neighboring atoms. 2c This answer is not correct. The mistake that you made is thinking that the geminal methyl groups were equivalent. Double bonds are not free to rotate and one of the methyl groups is on the side of the double bond with the ethyl group whereas the other methyl group is on the side of the double bond with the hydrogen atom. 2d - You are correct!

3a This answer is not correct. Every carbon atom has a hydrogen atom bonded to it so the number of hydrogen absorptions must equal the number of carbon absorptions. There are 4 absorptions for both spectra for this compound. Think about the unique positions of the groups...their neighboring atoms...and try another selection. 3b You are correct! 3c This answer is not correct. Perhaps you thought that only 2 of the 3 methyl groups on the left side of the molecule were equivalent. They are all the same and should be counted as 1 absorption. See if you can find a better answer with this thought in mind. 3d This answer is not correct. Every carbon atom has a hydrogen atom bonded to it so the number of hydrogen absorptions must equal the number of carbon absorptions. There are 5 absorptions for both spectra for this compound. Think about the unique positions of the groups...their neighboring atoms...and try another selection.

4a You are correct! There should be equal numbers of absorptions in both spectra and there are 4 unique positions in the molecule. Note that the molecule is symmetrical with respect to the red line...

4b This answer is not correct. There should be equal numbers of absorptions in both spectra for this compound and there are 5 unique positions in the molecule. Note that the molecule is symmetrical with respect to the red line...

4c This answer is not correct. There should be 4 hydrogen absorptions and 5 carbon absorptions for this molecule. Remember that there is no hydrogen atom on the carbon atom with the geminal methyl groups. Note that the molecule is symmetrical with respect to the red line...

4d This answer is not correct. There should be equal numbers of absorptions in both spectra for this compound and there are only 3 unique positions in the molecule. Note that the molecule is symmetrical with respect to the red line...

5a This answer is not correct. The hydrogen atoms on adjacent carbon atoms can "couple" with these hydrogen atoms and split the absorption into multiple lines (multiplet). The formula for calculating the lines for a multiplet based on adjacent hydrogen atoms having a spin quantum number of is...the number of lines = n+1 where "n" = the number of hydrogen atoms on adjacent carbon atoms. How many hydrogen atoms are on adjacent carbon atoms?

5bThis answer is not correct. The hydrogen atoms on adjacent carbon atoms can "couple" with these hydrogen atoms and split the absorption into multiple lines (multiplet). The formula for calculating the lines for a multiplet based on adjacent hydrogen atoms having a spin quantum number of is...the number of lines = n+1 where "n" = the number of hydrogen atoms on adjacent carbon atoms. How many hydrogen atoms are on adjacent carbon atoms?

5c You are correct! The number of hydrogen atoms on the adjacent carbon atom is 3. The formula then give 3+1=4.

5d This answer is not correct. Perhaps you thought that the methyl group attached to the carbonyl group coupled with the methylene hydrogen atoms. These hydrogen atoms are too far distant to show coupling. Only hydrogen atoms on adjacent carbon atoms can "couple" with these hydrogen atoms. With this in mind, select another answer.

6c This answer is not correct. The chemical shift for a methylene group attached to a cyano group is 2.9 ppm but the downfield multiplet in the spectrum is at 3.4 ppm. See if another answer better fits the data.

6d This answer is not correct. The chemical shift for a methine group attached to a cyano group should be 2.9 ppm whereas the downfield multiplet in the spectrum is at 3.4 ppm. The isopropyl group should also show an upfield doublet and a downfield heptet and the multiplets in the spectrum are a triplet and a quartet. Think about both the chemical shift and the group pattern and try again.

7a You are correct! The isobutyl group will show a large upfield doublet for the 2 methyl groups, a small downfield doublet for the methylene group and a "triplet of heptets" for the methine group.

7bThis answer is not correct. This group will show a very large upfield singlet for the 3 methyl groups, a small downfield triplet for the terminal methylene group and another triplet for the other methylene group. 7c This answer is not correct. The secondary butyl group will show 4 unique absorptions instead of 3 and the multiplicities of the groups will be completely different than the pattern shown. Think about the number of absorptions and also the number of hydrogen atoms on adjacent carbon atoms and try again. 7d This answer is not correct. The 1-propyl group will show 3 absorptions but the downfield absorption will be a triplet as will the upfield absorption. The central methylene group will be a triplet of quartets...it will look a lot like a hextet.

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Introduction to spectroscopy
Multiple choice questions
Try the following multiple choice questions to test your knowledge of this chapter. For each question there is one correct answer. The periodic table, physical constants and relative atomic masses needed for these problems are given on the inside covers of Chemistry, fourth edition by C.E. Housecroft and E.C. Constable. Once you have answered the questions, click on 'Submit Answers for Grading' to get your results. If your lecturer has requested that you send your results, please complete the routing information found at the bottom of your graded page and then click on the 'E-Mail Results' button. Please do not forward your results unless your lecturer has specifically requested that you do so.
This activity contains 18 questions.

The wavenumber of a transition is 2000 cm1. In what part of the electromagnetic spectrum does this come?
Infrared. Radiowave. Microwave. Ultraviolet-visible.

The frequency of a transition is 5.4 1015 Hz. What is the corresponding wavelength?
560 nm 180 000 cm1 5.6 106 m 5.6 108 m

According to the Beer-Lambert Law, on which of the following does absorbance not depend?
Extinction coefficient of the sample. Colour of the solution. Solution concentration. Distance that the light has travelled through the sample.

What is the name of an instrument used to measure the absorbance of a coloured compound in solution?
Colourmeter. Coulometer. Colorimeter. Calorimeter.

A solution of X of concentration 0.010 mol dm3 gives an absorbance of 0.5. What concentration is a

solution of X which gives an absorbance reading of 0.25? Assume that the same optical cell is used for both readings.
0.050 mol dm3 0.010 mol dm3 0.0050 mol dm3 0.020 mol dm3

Compound Z absorbs light of wavelength 320 nm. A 1.0 103 mol dm3 solution of a compound Z gives an absorbance reading of 0.15 when placed in a solution cell of path length 1 cm. What is the value of the molar extinction (absorption) coefficient of Z?
15 dm3 mol1 cm1 1500 dm3 mol1 cm1 150 dm3 mol1 cm1 1.5 104 mol dm3 cm1

The dichromate ion absorbs light of wavelength close to 500 nm. Based on this information, what can you conclude?
The dichromate ion absorbs in the ultraviolet region. The dichromate ion absorbs within the visible region. Solutions of the dichromate ion are colourless. The dichromate ion absorbs outside the visible region.

A solution of a dye absorbs light of wavelength 480 nm, and for this absorption, the extinction coefficient is 18600 dm3 mol1 cm1. A sample of the dye of unknown concentration is placed in an optical cell of path length 1 cm and the absorbance reading is 0.18. What is the concentration of the solution?
2.0 108 mol dm3 9.7 106 mol dm3 3.0 104 mol dm3 0.026 mol dm3

The wavelength of an absorption is 495 nm. In what part of the electromagnetic spectrum does this lie?
Radiowave. Infrared. Microwave. Ultraviolet-visible.

The frequency of a transition is 3.1 1010 Hz. What is the energy of this transition?
2.1 1044 kJ 2.1 1044 J 2.0 1023 J 2.0 1023 kJ

Which of the following statements is correct?


Infrared radiation has a shorter wavelength than visible light. Microwave radiation possesses more energy than infrared radiation. Infrared radiation has a lower wavenumber than visible light. Ultraviolet radiation has a longer wavelength than infrared radiation.

A solution of compound Z absorbs light of wavelength 256 nm, and for this absorption, log = 3.3. What is the concentration of a solution of Z (in an optical cell of path length 1 cm) that gives the absorbance reading is 0.21?
5.0 104mol dm3 1.1 104 mol dm3 2.4 103 mol dm3 0.064 mol dm3

Which statement is correct?


Wavelength is directly proportional to energy. Wavenumber is directly proportional to wavelength. Wavenumber is directly proportional to energy. Wavelength is directly proportional to frequency.

Aqueous KMnO4 solutions are purple. A plot of absorbance against concentration is:
linear with a negative gradient. linear with a positive gradient. an exponential curve. non-linear.

A shift to lower wavenumber for an absorption in a spectrum corresponds to:


a shift to higher energy. a loss of intensity. a shift to lower wavelength. a shift to lower frequency.

An absorption in an electronic spectrum is recorded at 17 000 cm1. What does this correspond to in nm?
59 nm 5900 nm 590 nm 59 000 nm

A 0.100 mol dm3 aqueous solution of a nickel(II) salt shows three absorbances, one of which has a value of = 2.95 dm3 mol1cm1. What is the corresponding absorbance, if the path length of the solution cell used for the measurement is 1.00 cm?
0.0340 0.295 0.340 29.5

A copper(II) sulfate solution of unknown concentration is placed in a colorimeter and an absorbance reading of 0.46 is recorded. Using the same solution cell, a 0.055 solution of copper(II) sulfate gives an absorbance reading of 0.34. What is the concentration of the first solution?
0.041 mol dm3 8.60 103 mol dm3 0.074 mol dm3 0.35 mol dm3

Results for: "Multiple choice questions"

1.

The wavenumber of a transition is 2000 cm1. In what part of the electromagnetic spectrum does this come? Your Answer: Infrared.

2.

The frequency of a transition is 5.4 1015 Hz. What is the corresponding wavelength?

1 Your Answer: 180 000 cm 8 Correct Answer: 5.6 10 m

3.

According to the Beer-Lambert Law, on which of the following does absorbance not depend? Your Answer: Extinction coefficient of the sample. Correct Answer: Colour of the solution.

4.

What is the name of an instrument used to measure the absorbance of a coloured compound in solution? Your Answer: Colorimeter.

5.

A solution of X of concentration 0.010 mol dm3 gives an absorbance of 0.5. What concentration is a solution of X which gives an absorbance reading of 0.25? Assume that the same optical cell is used for both readings.
3 Your Answer: 0.0050 mol dm

6.

Compound Z absorbs light of wavelength 320 nm. A 1.0 10 3 mol dm3 solution of a compound Z gives an absorbance reading of 0.15 when placed in a solution cell of path length 1 cm. What is the value of the molar extinction (absorption) coefficient of Z?
3 1 1 Your Answer: 1500 dm mol cm 3 1 1 Correct Answer: 150 dm mol cm

7.

The dichromate ion absorbs light of wavelength close to 500 nm. Based on this information, what can you conclude? Your Answer: The dichromate ion absorbs in the ultraviolet region. Correct Answer: The dichromate ion absorbs within the visible region.

8.

A solution of a dye absorbs light of wavelength 480 nm, and for this absorption, the extinction coefficient is 18600 dm3 mol1 cm1. A sample of the dye of unknown concentration is placed in an optical cell of path length 1 cm and the absorbance reading is 0.18. What is the concentration of the solution?
6 3 Your Answer: 9.7 10 mol dm

9.

The wavelength of an absorption is 495 nm. In what part of the electromagnetic spectrum does this lie? Your Answer: Microwave. Correct Answer: Ultraviolet-visible.

10.

The frequency of a transition is 3.1 1010 Hz. What is the energy of this transition?
23 J Your Answer: 2.0 10

11.

Which of the following statements is correct? Your Answer: Infrared radiation has a lower wavenumber than visible light.

12.

A solution of compound Z absorbs light of wavelength 256 nm, and for this absorption, log = 3.3. What is the concentration of a solution of Z (in an optical cell of path length 1 cm) that gives the absorbance reading is 0.21?
4 3 Your Answer: 5.0 10 mol dm 4 3 Correct Answer: 1.1 10 mol dm

13.

Which statement is correct? Your Answer: (blank)

14.

Aqueous KMnO4 solutions are purple. A plot of absorbance against concentration is: Your Answer: linear with a positive gradient.

15.

A shift to lower wavenumber for an absorption in a spectrum corresponds to: Your Answer: a loss of intensity. Correct Answer: a shift to lower frequency.

16.

An absorption in an electronic spectrum is recorded at 17 000 cm1. What does this correspond to in nm? Your Answer: 590 nm

17.

A 0.100 mol dm3 aqueous solution of a nickel(II) salt shows three absorbances, one of which has a value of = 2.95 dm3 mol1 cm1. What is the corresponding absorbance, if the path length of the solution cell used for the measurement is 1.00 cm? Your Answer: 0.295

18.

A copper(II) sulfate solution of unknown concentration is placed in a colorimeter and an absorbance reading of 0.46 is recorded. Using the same solution cell, a 0.055 solution of copper(II) sulfate gives an absorbance reading of 0.34. What is the concentration of the first solution?
3 Your Answer: 0.074 mol dm

================================ Vibrational Rotational Spectroscopy


Multiple choice questions
Try the following multiple choice questions to test your knowledge of this chapter. For each question there is one correct answer. The periodic table, physical constants and relative atomic masses needed for these problems are given on the inside covers of Chemistry, fourth edition by C.E. Housecroft and E.C. Constable. Once you have answered the questions, click on 'Submit Answers for Grading' to get your results. If your lecturer has requested that you send your results, please complete the routing information found at the bottom of your graded page and then click on the 'E-Mail Results' button. Please do not forward your results unless your lecturer has specifically requested that you do so.
This activity contains 18 questions.

Which statement is correct about the vibrational ground state of an H2 molecule?


The molecule is in its lowest vibrational level but is not vibrating. In its vibrational ground state, the molecule has no vibrational energy. The molecule is static in its ground state. The molecule is vibrating.

Which value is the correct reduced mass of HF?


6.30 1026 kg 1.59 1027 kg 1.75 1027 kg 5.72 1026 kg

The force constants for CO and CS are 1902 and 849 N m1 respectively. Which statement is incorrect?
The wavenumber associated with the stretching of CO is higher than that of CS. Stretching the bond in CO requires less energy than stretching the bond in CS. Less energy is required to dissociate CS than CO. The trend in bond energies for CO and CS follows the trend in force constants.

Which statement is incorrect about CO2?


The IR spectrum of CO2 shows four absorptions. CO2 has two degenerate bending modes of vibration. CO2 is linear. CO2 has two stretching modes of vibration.

Which statement is incorrect about H2O?


H2O is non-linear. H2O has four degrees of vibrational freedom. H2O undergoes symmetric and asymmetric stretching modes of vibration. H2O has three IR active modes of vibration.

Match the molecular formula to the number of degrees of vibrational freedom. Which pair is correct?
CO2; 3. CS2; 3. H2S; 4. SO2; 3.

In the IR spectrum of a ketone (R2C=O), in what approximate region would you expect to find an absorption assigned to the C=O stretch?

2000-2100 cm1 1900-2000 cm1 1400-1500 cm1 1700-1750 cm1

Which is the correct sequence of wavenumbers associated with the stretching of the following bonds?
CI > CCl < C=O < CN CI < CCl < C=O < CN CI > CCl > C=O > CN CI > CCl > C=O < CN

The IR spectrum of methanol (CH3OH) shows strong absorptions at 3340 (broad), 2945, 2833 and 1030 cm1. Which band is assigned to the OH stretch?
1030 cm1 2833 cm1 2945 cm1 3340 cm1

Hex-1-yne is a hydrocarbon with a terminal HCC (alkyne) group. The remaining part of the molecule contains CH2 groups and a terminal CH3 group. The IR spectrum of hex-1-yne shows relatively strong absorptions at 3311, 2962, 2937, 2876 and 2120 cm 1as well as absorptions below 1500 cm1. Which bands are assigned to the CC and terminal HC(alkyne) stretches?
CC, 2120 cm1; HC(alkyne), 3311 cm1 CC, 3311 cm1; HC(alkyne), 2120 cm1 CC, 2120 cm1; HC(alkyne), 2876 cm1 CC, 2962 cm1; HC(alkyne), 3311 cm1

n-Propylbenzene contains C(sp2)H and C(sp3)H bonds. The IR spectrum of propylbenzene contains strong or medium absorptions at 3085, 3064, 3028, 2960, 2931 and 2873 cm 1 as well as bands below 1600 cm1. Which statement is incorrect?
Absorptions at 3085, 3064 and 3028 cm1 are assigned to the stretching of the C(sp2)H bonds. Stretching of the C(sp3)H bonds gives rise to absorptions at lower wavenumbers than stretching of the C( sp2)H bonds. Each absorption can be assigned to the stretching mode of a particular bond in the propylbenzene molecule. Absorptions at 2960, 2931 and 2873 cm1 are assigned to the stretching of the C(sp3)H bonds.

The IR spectrum of CBr4 has a strong absorption at 667 cm1. Which is the correct assignment of this absorption?
The stretching of one CBr bond. A bending mode. The asymmetric stretching of the four C Br bonds. The symmetric stretching of the four CBr bonds.

The force constant for the bond in NO is 1595 N m1. Where will you observe an absorption in the IR spectrum of NO assigned to the stretching mode?
1903 cm1 1193 cm1 190 cm1 2170 cm1

The IR spectrum of liquid cyclohexanol contains a broad band at 3331 cm1. Which of the following statements correctly describes what happens if the IR spectrum is re-recorded after D2O has been added to the alcohol?
A new band near to 3800 cm1 is observed. The absorption at 3331 cm1 becomes very sharp. The absorption at 3331 cm1 becomes more intense. A new band near to 2500 cm1 is observed.

What is the moment of inertia, IB, of 1H79Br if the bond distance is 142 pm? Atomic masses are: 1H = 1.008, 79Br = 78.92.
3.33 1047 kg m2 3.00 1046 kg m2 2.34 1037 kg m2 1.22 107 kg m2

Which of the following statements is correct about the principal moments of inertia of an XY molecule that lies on the A axis?
IA = IB, and IC = 0 IA > IB, and IB = IC IA = 0, and IB = IC IA = IB = IC

For which of the following molecules could a pure rotational spectrum not be observed in the gas phase?
N2 HCl CO NO

Which of the following transitions between rotational energy levels is not allowed?
J=1J=3 J=0J=1 J=1 J=0 J=1J=2

Results for: "Multiple choice questions"

1.

Which statement is correct about the vibrational ground state of an H2 molecule? Your Answer: In its vibrational ground state, the molecule has no vibrational energy. Correct Answer: The molecule is vibrating.

2.

Which value is the correct reduced mass of HF?


27 kg Your Answer: 1.75 10 27 kg Correct Answer: 1.59 10

3.

The force constants for CO and CS are 1902 and 849 N m1 respectively. Which statement is incorrect? Your Answer: Stretching the bond in CO requires less energy than stretching the bond in CS.

4.

Which statement is incorrect about CO2? Your Answer: The IR spectrum of CO2 shows four absorptions.

5.

Which statement is incorrect about H2O? Your Answer: H2O undergoes symmetric and asymmetric stretching modes of vibration. Correct Answer: H2O has four degrees of vibrational freedom.

6.

Match the molecular formula to the number of degrees of vibrational freedom. Which pair is correct? Your Answer: H2S; 4. Correct Answer: SO2; 3.

7.

In the IR spectrum of a ketone (R2C=O), in what approximate region would you expect to find an absorption assigned to the C=O stretch?
1 Your Answer: 2000-2100 cm 1 Correct Answer: 1700-1750 cm

8.

Which is the correct sequence of wavenumbers associated with the stretching of the following bonds? Your Answer: CI > CCl > C=O > CN Correct Answer: CI < CCl < C=O < CN

9.

The IR spectrum of methanol (CH3OH) shows strong absorptions at 3340 (broad), 2945, 2833 and 1030 cm1. Which band is assigned to the OH stretch?
1 Your Answer: 2833 cm 1 Correct Answer: 3340 cm

10.

Hex-1-yne is a hydrocarbon with a terminal H CC (alkyne) group. The remaining part of the molecule contains CH2 groups and a terminal CH3 group. The IR spectrum of hex-1-yne shows relatively strong absorptions at 3311, 2962, 2937, 2876 and 2120 cm1 as well as absorptions below 1500 cm1. Which bands are assigned to the CC and terminal HC(alkyne) stretches?
1 1 Your Answer: CC, 3311 cm ; HC(alkyne), 2120 cm 1 1 Correct Answer: CC, 2120 cm ; HC(alkyne), 3311 cm

11.

n-Propylbenzene contains C(sp2)H and C(sp3)H bonds. The IR spectrum of propylbenzene contains strong or medium absorptions at 3085, 3064, 3028, 2960, 2931 and 2873 cm 1 as well as bands below 1600 cm1. Which statement is incorrect? Your Answer: Each absorption can be assigned to the stretching mode of a particular bond in the propylbenzene molecule.

12.

The IR spectrum of CBr4 has a strong absorption at 667 cm1. Which is the correct assignment of this absorption? Your Answer: The symmetric stretching of the four CBr bonds. Correct Answer: The asymmetric stretching of the four C Br bonds.

13.

The force constant for the bond in NO is 1595 N m1. Where will you observe an absorption in the IR spectrum of NO assigned to the stretching mode?
1 Your Answer: 1193 cm 1 Correct Answer: 1903 cm

14.

The IR spectrum of liquid cyclohexanol contains a broad band at 3331 cm 1. Which of the following statements correctly describes what happens if the IR spectrum is re-recorded after D2O has been added to the alcohol?
1 Your Answer: The absorption at 3331 cm becomes very sharp. 1 Correct Answer: A new band near to 2500 cm is observed.

15.

What is the moment of inertia, IB, of 1H79Br if the bond distance is 142 pm? Atomic masses are: 1H = 1.008, 78.92.
46 2 Your Answer: 3.00 10 kg m 47 kg m2 Correct Answer: 3.33 10

79

Br =

16.

Which of the following statements is correct about the principal moments of inertia of an XY molecule that lies on

the A axis? Your Answer: IA = 0, and IB = IC

17.

For which of the following molecules could a pure rotational spectrum not be observed in the gas phase? Your Answer: CO Correct Answer: N2

18.

Which of the following transitions between rotational energy levels is not allowed? Your Answer: J = 1 J = 3

Electronic Spectroscopy
Multiple choice questions
Try the following multiple choice questions to test your knowledge of this chapter. For each question there is one correct answer. The periodic table, physical constants and relative atomic masses needed for these problems are given on the inside covers of Chemistry, fourth edition by C.E. Housecroft and E.C. Constable. Once you have answered the questions, click on 'Submit Answers for Grading' to get your result s. If your lecturer has requested that you send your results, please complete the routing information found at the bottom of your graded page and then click on the 'E-Mail Results' button. Please do not forward your results unless your lecturer has specifically requested that you do so.
This activity contains 18 questions.

In which region of the electromagnetic spectrum does an absorption at 600 nm come?


Near -UV. Infrared. Visible. Vacuum-UV.

A solution of 0.001 mol dm3 NiSO4 is placed in an optical cell of pathlength 1 cm, and the absorption spectrum is recorded. The absorptions have characteristic max and max values. What are the correct units of max?
mol dm3 cm1 cm mol dm3 cm dm3 mol1 dm3 mol1 cm1

In which region of the electromagnetic spectrum does an absorption at 177 nm come?


Visible. Vacuum-UV. Near -UV.

Infrared.

What does the notation *n mean?


Absorption; transition from a quantum level n to * MO. Emission; transition from a quantum level n to * MO. Emission; transition from a non-bonding MO to * MO. Absorption; transition from a non-bonding MO to * MO.

How do values of max for the * transitions vary among a series of conjugated polyenes?
Values shift to longer wavelength as the number of C=C double bonds increases. Values vary very little. Values vary but in no particular pattern. Values shift to shorter wavelength as the number of C=C double bonds increases.

What is a red shift?


The shifting of an absorption towards the blue end of the spectrum. The shifting of an absorption to lower energy. The shifting of an absorption to higher energy. The shifting of an absorption to shorter wavelength.

What is a chromophore?
A group of atoms in a coloured compound. A group of atoms in a compound responsible for electromagnetic radiation. A coloured compound. A group of atoms in a compound responsible for the absorption of electromagnetic radiation.

Which of the following is the principal chromophore in an azo-dye?


N=N C=N NN CN

Lycopene (max = 469 nm) is present in tomatoes. What colour of light does lycopene absorb?
Red. Orange. Blue. Green.

In which of the following are the -electrons not delocalized?


Hepta-1,6-diene. An ,-unsaturated ketone. Buta-1,3-diene. Allyl anion.

All but one of the following groups can donate a lone pair of electrons into the carbon -system of a conjugated polyene. Which is the odd one out?
OMe Me SMe NMe2

Which statement is incorrect about the allyl anion and buta-1,3-diene?


Both have four -electrons. In both, the -bonding is delocalized. Both have four MOs. In both, the C atoms are all sp2 hybridized.

Which of the following arrangements of carbon-carbon double bonds along the backbone of a polyene does not correspond to a conjugated system?
C=CC=CC=C C=CC=CC=CC=C C=CCC=C C=CC=C

An aqueous solution of a dye has a strong absorption with max= 464 nm. The colour of the solution is:
green. colourless. orange. purple.

Which of the following absorption maxima is not in the visible range of the electronic spectrum?
max = 550 nm max = 250 nm max = 750 nm max = 480 nm

Which of the following statements is consistent with an electronic absorption being broad?
Hydrogen bonding causes an electronic absorption to be broad. Electronic transitions are always localized on a single atomic centre. An electronic absorption includes vibrational and rotational structure. The absorption of a photon is slower than the timescale of molecular vibrations.

Two solutions of the same compound were made up. Solution A was of concentration 0.98 10 4 mol dm3, and solution B was 1.66 102 mol dm3. The electronic spectrum of solution A contained one absorption at max = 230 nm, while the spectrum of solution B contained absorptions at max = 230 and 365 nm. The difference in the spectra was because:
max for the absorption at 365 nm is much smaller than max of the band at 230 nm. the value of max depends on concentration. electronic spectroscopic data are not always reproducible. the value of max depends on concentration.

A compound X is characterized in its electronic spectrum by an absorption with max = 217 nm (max = 21 000 dm3 mol1 cm1). Of the compounds given below, X is most likely to be:
-carotene. water. buta-1,3-diene. ethanol.

Results for: "Multiple choice questions"

1.

In which region of the electromagnetic spectrum does an absorption at 600 nm come? Your Answer: Infrared. Correct Answer: Visible.

2.

A solution of 0.001 mol dm3 NiSO4 is placed in an optical cell of pathlength 1 cm, and the absorption spectrum is recorded. The absorptions have characteristic max and max values. What are the correct units of max?
3 Your Answer: cm mol dm 3 1 1 Correct Answer: dm mol cm

3.

In which region of the electromagnetic spectrum does an absorption at 177 nm come? Your Answer: Visible. Correct Answer: Vacuum-UV.

4.

What does the notation *n mean? Your Answer: Emission; transition from a non-bonding MO to * MO. Correct Answer: Absorption; transition from a non-bonding MO to * MO.

5.

How do values of max for the * transitions vary among a series of conjugated polyenes? Your Answer: Values vary but in no particular pattern. Correct Answer: Values shift to longer wavelength as the number of C=C double bonds increases.

6.

What is a red shift? Your Answer: (blank)

7.

What is a chromophore? Your Answer: A coloured compound. Correct Answer: A group of atoms in a compound responsible for the absorption of electromagnetic radiation.

8.

Which of the following is the principal chromophore in an azo-dye? Your Answer: C=N Correct Answer: N=N

9.

Lycopene (max = 469 nm) is present in tomatoes. What colour of light does lycopene absorb? Your Answer: Blue.

10.

In which of the following are the -electrons not delocalized? Your Answer: Buta-1,3-diene. Correct Answer: Hepta-1,6-diene.

11.

All but one of the following groups can donate a lone pair of electrons into the carbon -system of a conjugated polyene. Which is the odd one out? Your Answer: SMe Correct Answer: Me

12.

Which statement is incorrect about the allyl anion and buta-1,3-diene? Your Answer: Both have four MOs.

13.

Which of the following arrangements of carbon-carbon double bonds along the backbone of a polyene does not correspond to a conjugated system? Your Answer: C=CC=CC=CC=C Correct Answer: C=CCC=C

14.

An aqueous solution of a dye has a strong absorption with max= 464 nm. The colour of the solution is: Your Answer: orange.

15.

Which of the following absorption maxima is not in the visible range of the electronic spectrum? Your Answer: max = 550 nm Correct Answer: max = 250 nm

16.

Which of the following statements is consistent with an electronic absorption being broad? Your Answer: An electronic absorption includes vibrational and rotational structure.

17.

Two solutions of the same compound were made up. Solution A was of concentration 0.98 104 mol dm3, and solution B was 1.66 102 mol dm3. The electronic spectrum of solution A contained one absorption at max = 230 nm, while the spectrum of solution B contained absorptions at max = 230 and 365 nm. The difference in the spectra was because: Your Answer: electronic spectroscopic data are not always reproducible. Correct Answer: max for the absorption at 365 nm is much smaller than max of the band at 230 nm.

18.

A compound X is characterized in its electronic spectrum by an absorption with max = 217 nm (max = 21 000 dm3 mol1 cm1). Of the compounds given below, X is most likely to be: Your Answer: buta-1,3-diene.

===================== http://www.indiabix.com/biochemistry/nmr-spectroscopy/
1. What is shielding in NMR? A. B. C. Using a curved piece of metal to block an opponents attack Putting metal around an Rf source When the magnetic moment of an atom blocks the full induced magnetic field from surrounding nuclei

D.

Blocking parts of a molecule from Rf radiation

Answer & Explanation

Answer: Option C

2.

What is used to cool the superconducting coil? A. B. C. D. Hydrogen Ice Dry ice Liquid helium

Answer & Explanation

Answer: Option D

3.

Coupling causes the peaks in 1H NMR spectra to be split into A. B. C. D. two peaks multiple peaks equal to the number of hydrogens on surrounding atoms multiple peaks equal to the number of surrounding carbon atoms multiple peaks equal to the number of hydrogen on surrounding atoms, plus one

Answer & Explanation

Answer: Option D

4.

When placed in a magnetic field, all the random spins of the nuclei A. B. C. D. stop reverse direction align with the magnetic field rotate to 90 away from the induced field

Answer & Explanation

Answer: Option C

5.

Better understanding of the nuclei is possible, A. with the help of wavelength spectrum

B. C. D.

with the help of frequencies ranges with the help of a mathematical translator called the fourier transfer algorithm none of the above

Answer & Explanation

Answer: Option C

6.

All hydrogen atoms A. B. C. D. have the same resonance frequency resonate at different frequencies depending on their environment. are attached to carbon resonate at about the same frequency as carbon

Answer & Explanation

Answer: Option B

7.

Why is it important to use a deuterated solvent? A. B. C. D. NMR uses least of this solvent So the spectrometer can lock onto the sample to prevent the spectrum from drifting during aquisition Expensive solvents work best with NMR They dissolve polymer the fastest

Answer & Explanation

Answer: Option B

http://highered.mcgraw-hill.com/sites/0072397462/student_view0/chapter15/multiple_choice_quiz.html
Multiple Choice Quiz

1 Which of the following statements is FALSE about the NMR experiment.


A) B) C) D) The energy required to flip the spin of a proton is in the infrared region of the electromagnetic spectrum. The energy difference between the two spin states depends on the strength of the magnetic field. When energy absorption occurs, the nuclei are said to be in resonance with the electromagnetic radiation. When a proton is aligned with the magnetic field, its energy is lower than when it is aligned against the magnetic field.

2 When an external magnetic field is applied, what happens to the protons in a sample?
A) B) C) D) All protons align with the field. All protons align opposite to the field. Some protons align with the field and some align opposite to it. All protons assume a random orientation

3 Which of the following statements about the energy of an applied magnetic field is FALSE?
A) B) C) D) This energy can flip a proton from alignment with the field to alignment opposite the field. Nuclei are in resonance when they absorb this energy. This energy is proportional to the magnetic field strength. This energy is supplied by radiation in the visible region of the spectrum.

4 Which of the following compounds has the MOST deshielded protons?


A) B) C) D) CH3Cl CH3I CH3Br CH4

5 Which of the following compounds has the MOST deshielded methyl protons?
A) B) C) tetramethylsilane methyl fluoride methanol methylamine

D)

6 What is the value of the chemical shift for an absorption at 1800 Hz from tetramethylsilane (TMS) using an NMR spectrometer with an
operating frequency of 300 MHz? A) B) C) D) 1.66 ppm 16.6 ppm 6.0 ppm 4.0 ppm

7 The chemical shift of the protons in acetone is 2.06. How many hertz downfield from TMS will the resonance appear in a spectrum taken on
a spectrometer operating at 300 MHz? A) B) C) D) 300 Hz 618 Hz 3000 Hz 6.18 x 108 Hz

8 Arrange the following compounds in order of decreasing chemical shift for the underlined hydrogens (largest value first, smallest value
last). CH3CH2CH3 CH3OCH2CH3 Cl2CHCH2CH3 ClCH2CH2CH3 a b c d

A) B) C) D)

b>c>a>d b>c>d>a c>b>a>d c>b>d>a

9 How many signals would the following molecule show in its

H NMR spectrum?

A) B) C) D)

5 1 6 8

10 An unknown molecule A has 4 signals in the


A)

H NMR spectrum. Which of the following corresponds to molecule A?

B)

C)

D)

11 How many nonequivalent protons does the following structure have?

A) B) C) D)

12 8 6 4

12 How many nonequivalent protons does the following structure have?

A) B) C) D)

6 5 4 3

13 How many sets of protons are equivalent in meta-xylene (1,3-dimethylbenzene)?

A) B) C) D)

2 3 4 5

14 Reading from left to right, what multiplicity would be found for the three nonequivalent sets of protons in the
following compound?

H NMR spectrum of the

A) B) C)

s, s, s d, d, s s, d, d

D)

s, s, d

15 What is the splitting pattern of the methylene protons in propane?


A) B) C) D) triplet quartet doublet septet

16 The signal for the methylene protons of butane is split into a


A) B) C) D) doublet. triplet. quartet. quintet.

17 Give the number of lines in the coupling pattern for each type of hydrogen.

A) B) C) D)

a=2, b=7, c=1, d=1 a=2, b=8, c=2, d=1 a=2, b=7, c=7, d=2 a =2, b=8,c=8, d=2

18 Propose a structure for the following compound.


1

H NMR spectrum of C5H8O2: 1.90 (multiplet, 4H) 2.40 (triplet, 2H) 4.26 (triplet, 2H) A)

B)

C)

D)

19 Which

H NMR spectrum represents the following compound?

A)

B)

C)

D)

H NMR spectrum 0.90 (quartet, 2H) 2.28 (triplet, 2H) 3.00 (triplet, 1H) 4.50 (triplet, 1H) 1 H NMR spectrum 1.50 (doublet, 4H) 3.80 (septet, 1H) 5.50 (triplet, 1H) 1 H NMR spectrum 1.00 (triplet, 3H) 1.20 (quartet, 1H) 2.00 (quartet, 2H) 1 H NMR spectrum 1.90 (quintet, 2H) 2.28 (triplet, 4H)
1

20 An unknown compound A has the molecular formula C H O . Based on the following


4 8 2

H NMR spectrum, what is the structure of compound A?

A)

B)

C)

D)

21 The

H NMR spectrum of a compound is shown below. What is the structure of the compound?

A)

B)

C)

D)

22 A compound of formula C H
5

12

gives 1 signal in the 1H NMR and 2 signals in the

13

C NMR. The compound is

A) B) C) D)

pentane. 2-methylbutane. 2,2-dimethylpropane. Cannot tell without more information.

23 There are several compounds with the molecular formula C H


5

10Br2.

Which isomer ad with this formula has the following 1H NMR spectrum?

(ppm) 1.0 (9H, singlet) 5.3 (1H, singlet)

A) B)

a b

C) D)

c d

24 How many methyl peaks would you expect to observe in the


A) B) C) D) 1 2 3 4

H NMR spectrum of cis-1,4-dimethylcyclohexane?

25 How many absorption bands will appear in the

13

C NMR spectrum for the following compound?

A) B) C) D)

4 6 7 8

26 How many absorption bands will appear in the

13

C NMR spectrum for the following compound?

A) B) C) D)

6 7 8 9

27 How many absorption bands will appear in the

13

C NMR spectrum for the following compound?

A) B) C) D)

5 7 8 9

28 How many resonances in the

13

C NMR spectrum would the following structure show?

A) B) C) D)

8 6 4 2

29 How many signals are expected in a


A) B) C) D) 4 5 6 7

13

C NMR spectrum of methylcyclohexane?

30 Deduce the structure of an unknown compound using the following


1

H NMR spectrum: 1.30 (triplet, 6H) 4.29 (quartet, 4H) 7.47.9 (multiplet, 4H)

H NMR spectrum, mass spectroscopy data, and IR spectrum.

Mass Spectrum:
m/e: 222 177 149 Intensity: (as % of base peak) 10% 38% 100%

IR Spectrum:
Intensity (peak): s m m s m-w m-w m m m s Frequency (cm1): 3100 2900 2800 1740 1600 1475 1465 1450 1375 13001000

A)

B)

C)

D)

Multiple Choice Quiz

Results Reporter
Out of 30 questions, you answered 6 correctly, for a final grade of 20%.

6 correct (20%) 22 incorrect (73%) 2 unanswered (7%)

Your Results:
The correct answer for each question is indicated by a .

INCORRECT

Which of the following statements is FALSE about the NMR experiment.

A)The energy required to flip the spin of a proton is in the infrared region of the electromagnetic spectrum.

B)The energy difference between the two spin states depends on the strength of the magnetic field.

C)When energy absorption occurs, the nuclei are said to be in resonance with the electromagnetic radiation.

D)When a proton is aligned with the magnetic field, its energy is lower than when it is aligned against the magnetic field.

CORRECT

When an external magnetic field is applied, what happens to the protons in a sample?

A)All protons align with the field.

B)All protons align opposite to the field.

C)Some protons align with the field and some align opposite to it.

D)All protons assume a random orientation

INCORRECT

Which of the following statements about the energy of an applied magnetic field is FALSE?

A)This energy can flip a proton from alignment with the field to alignment opposite the field.

B)Nuclei are in resonance when they absorb this energy.

C)This energy is proportional to the magnetic field strength.

D)This energy is supplied by radiation in the visible region of the spectrum.

CORRECT

Which of the following compounds has the MOST deshielded protons?

A)CH3Cl

B)CH3I

C)CH3Br

D)CH4

INCORRECT

Which of the following compounds has the MOST deshielded methyl protons?

A)tetramethylsilane

B)methyl fluoride

C)methanol

D)methylamine

UNANSWERED

What is the value of the chemical shift for an absorption at 1800 Hz from tetramethylsilane (TMS) using an NMR spectrometer with an operating frequency of 300 MHz?

A)1.66 ppm

B)16.6 ppm

C)6.0 ppm

D)4.0 ppm

INCORRECT

The chemical shift of the protons in acetone is 2.06. How many hertz downfield from TMS will the resonance appear in a spectrum taken on a spectrometer operating at 300 MHz?

A)300 Hz

B)618 Hz

C)3000 Hz

D)6.18 x 108 Hz

Arrange the following compounds in order of decreasing chemical shift for the underlined hydrogens (largest value first, smallest value last).

CORRECT

CH3CH2CH3 CH3OCH2CH3 Cl2CHCH2CH3 ClCH2CH2CH3 a b c d

A)b > c > a > d

B)b > c > d > a

C)c > b > a > d

D)c > b > d > a

How many signals would the following molecule show in its 1H NMR spectrum?

INCORRECT

A)5

B)1

C)6

D)8

10

CORRECT

An unknown molecule A has 4 signals in the 1H NMR spectrum. Which of the following corresponds to molecule A?

A)

B)

C)

D)

How many nonequivalent protons does the following structure have?

11

INCORRECT

A)12

B)8

C)6

D)4

How many nonequivalent protons does the following structure have?

12

CORRECT

A)6

B)5

C)4

D)3

How many sets of protons are equivalent in meta-xylene (1,3-dimethylbenzene)?

13

UNANSWERED

A)2

B)3

C)4

D)5

Reading from left to right, what multiplicity would be found for the three nonequivalent sets of protons in the 1H NMR spectrum of the following compound?

14

INCORRECT

A)s, s, s

B)d, d, s

C)s, d, d

D)s, s, d

15

CORRECT

What is the splitting pattern of the methylene protons in propane?

A)triplet

B)quartet

C)doublet

D)septet

16

INCORRECT

The signal for the methylene protons of butane is split into a

A)doublet.

B)triplet.

C)quartet.

D)quintet.

Give the number of lines in the coupling pattern for each type of hydrogen.

17

INCORRECT

A)a=2, b=7, c=1, d=1

B)a=2, b=8, c=2, d=1

C)a=2, b=7, c=7, d=2

D)a =2, b=8,c=8, d=2

18

INCORRECT

Propose a structure for the following compound. 1 H NMR spectrum of C5H8O2: 1.90 (multiplet, 4H) 2.40 (triplet, 2H) 4.26 (triplet, 2H)

A)

B)

C)

D)

Which 1H NMR spectrum represents the following compound?

19

INCORRECT

A)1H NMR spectrum 0.90 (quartet, 2H) 2.28 (triplet, 2H) 3.00 (triplet, 1H) 4.50 (triplet, 1H)

B)1H NMR spectrum 1.50 (doublet, 4H) 3.80 (septet, 1H) 5.50 (triplet, 1H)

C)1H NMR spectrum 1.00 (triplet, 3H) 1.20 (quartet, 1H) 2.00 (quartet, 2H)

D)1H NMR spectrum 1.90 (quintet, 2H) 2.28 (triplet, 4H)

An unknown compound A has the molecular formula C 4H8O2. Based on the following 1H NMR spectrum, what is the structure of compound A?

20

INCORRECT

A)

B)

C)

D)

21

INCORRECT

The 1H NMR spectrum of a compound is shown below. What is the structure of the compound?

A)

B)

C)

D)

22

INCORRECT

A compound of formula C5H12 gives 1 signal in the 1H NMR and 2 signals in the

13

C NMR. The compound is

A)pentane.

B)2-methylbutane.

C)2,2-dimethylpropane.

D)Cannot tell without more information.

There are several compounds with the molecular formula C 5H10Br2. Which isomer ad with this formula has the following 1H NMR spectrum? (ppm) 1.0 (9H, singlet) 5.3 (1H, singlet)

23

INCORRECT

A)a

B)b

C)c

D)d

24

INCORRECT

How many methyl peaks would you expect to observe in the 1H NMR spectrum of cis-1,4-dimethylcyclohexane?

A)1

B)2

C)3

D)4

How many absorption bands will appear in the

13

C NMR spectrum for the following compound?

25

INCORRECT

A)4

B)6

C)7

D)8

How many absorption bands will appear in the

13

C NMR spectrum for the following compound?

26

INCORRECT

A)6

B)7

C)8

D)9

How many absorption bands will appear in the

13

C NMR spectrum for the following compound?

27

INCORRECT

A)5

B)7

C)8

D)9

28

INCORRECT

How many resonances in the

13

C NMR spectrum would the following structure show?

A)8

B)6

C)4

D)2

29

INCORRECT

How many signals are expected in a

13

C NMR spectrum of methylcyclohexane?

A)4

B)5

C)6

D)7

Deduce the structure of an unknown compound using the following 1H NMR spectrum, mass spectroscopy data, and IR spectrum. 1 H NMR spectrum: 1.30 (triplet, 6H) 4.29 (quartet, 4H) 7.47.9 (multiplet, 4H)

Mass Spectrum: 30
INCORRECT m/e: 222 177 149 Intensity: (as % of base peak) 10% 38% 100%

IR Spectrum:
Intensity (peak): Frequency (cm1):

s m m s m-w m-w m m m s

3100 2900 2800 1740 1600 1475 1465 1450 1375 13001000

A)

B)

C)

D)

http://highered.mcgraw-hill.com/sites/0072397462/student_view0/chapter14/ 14
Mass Spectrometry and Infrared Spectroscopy

Multiple Choice Quiz

1 Not only the molecular ion peak, but all peaks in the mass spectrum of chlorobenzene are accompanied by a smaller peak one mass unit
higher. This peak is due to which of the following? A) B) C) D) capture of an H atom presence of a presence of a
13

C Cl

36

capture of a proton

2 Infrared spectroscopy provides valuable information about


A) B) C) D) molecular weight. melting point. conjugation. functional groups.

3 A strong signal at 1700 cm


A) B) C) D) alcohol ether carbonyl amine

in an IR spectrum indicates the presence of a(n)

4 A strong signal at 3400 cm


A) B) C) D) alcohol ether carbonyl amine

in an IR spectrum indicates the presence of a(n)

5 What is the exact mass (in atomic mass units: C, 12.0000; H, 1.0078; N, 14.0031; O, 15.9949) of the molecular ion of a compound with
molecular formula C3H8O? A) B) C) D) 60.0000 60.0573 60.0624 59.9949

6 Deduce the structure of an unknown compound with molecular formula C H


5

12O

using information given by its infrared spectrum.

Intensity (peak): Frequency (cm1): m m m m 3300 2900 2800 1465

m m

1450 1375

A)

B) C)

D)

7 Deduce the structure of an unknown compound with molecular formula C H Br using information given by an infrared spectrum.
3 3

Intensity (peak): Frequency (cm-1): m m-w m m m s 3300 2225 2800 1450 1375 667

A)

B)

C)

D)

8 Deduce the structure of an unknown compound with molecular formula C H


9

10O

using information given by its infrared spectrum.

Intensity (peak): Frequency (cm1): s m m s m-w m-w m m m 3100 2900 2800 1710 1600 1475 1465 1450 1375

A)

B)

C)

D)

9 Deduce the structure of an unknown compound with molecular formula C H O using information given by its infrared spectrum.
5 8

Intensity (peak): Frequency (cm1): m m s m-w m m 3100 2800 1705 1640 1450 1375

A)

B)

C)

D)

10 Which of the following bonds would be expected to have the highest frequency stretch?
A) B) C) D) carboncarbon single bond carboncarbon double bond carboncarbon triple bond carbonbromine single bond

11 Which of the following bonds would be expected to have the lowest frequency stretch?
A) B) C) D) C I CBr CCl C F

12 Which of the following compounds ad has an IR absorption at 1640 cm

A) B) C)

a b c

D)

13 Which of the following compounds ad has an IR absorption at 3300 cm

A) B) C) D)

a b c d

Results Reporter Your Results:


The correct answer for each question is indicated by a .

INCORRECT

Not only the molecular ion peak, but all peaks in the mass spectrum of chlorobenzene are accompanied by a smaller peak one mass unit higher. This peak is due to which of the following?

A)capture of an H atom

B)presence of a

13

C)presence of a

36

Cl

D)capture of a proton

INCORRECT Infrared spectroscopy provides valuable information about

A)molecular weight.

B)melting point.

C)conjugation.

D)functional groups.

1 INCORRECT A strong signal at 1700 cm in an IR spectrum indicates the presence of a(n)

A)alcohol

B)ether

C)carbonyl

D)amine

1 INCORRECT A strong signal at 3400 cm in an IR spectrum indicates the presence of a(n)

A)alcohol

B)ether

C)carbonyl

D)amine

INCORRECT

What is the exact mass (in atomic mass units: C, 12.0000; H, 1.0078; N, 14.0031; O, 15.9949) of the molecular ion of a compound with molecular formula C3H8O?

A)60.0000

B)60.0573

C)60.0624

D)59.9949

Deduce the structure of an unknown compound with molecular formula C 5H12O using information given by its infrared spectrum.

INCORRECT

Intensity (peak): Frequency (cm1): m 3300

m m m m m

2900 2800 1465 1450 1375

A)

B)

C)

D)

Deduce the structure of an unknown compound with molecular formula C 3H3Br using information given by an infrared spectrum. Intensity (peak): Frequency (cm-1): m m-w m m m s 3300 2225 2800 1450 1375 667

INCORRECT

A)

B)

C)

D)

Deduce the structure of an unknown compound with molecular formula C 9H10O using information given by its infrared spectrum. Intensity (peak): Frequency (cm1): s m m 3100 2900 2800 1710 1600 1475 1465 1450 1375

INCORRECT

s m-w m-w m m m

A)

B)

C)

D)

INCORRECT

Deduce the structure of an unknown compound with molecular formula C 5H8O using information given by its infrared spectrum.

Intensity (peak): Frequency (cm1): m m s m-w m m 3100 2800 1705 1640 1450 1375

A)

B)

C)

D)

10

INCORRECT Which of the following bonds would be expected to have the highest frequency stretch?

A)carboncarbon single bond

B)carboncarbon double bond

C)carboncarbon triple bond

D)carbonbromine single bond

11

INCORRECT Which of the following bonds would be expected to have the lowest frequency stretch?

A)CI

B)CBr

C)CCl

D)CF

Which of the following compounds ad has an IR absorption at 1640 cm1?

12

INCORRECT

A)a

B)b

C)c

D)d

Which of the following compounds ad has an IR absorption at 3300 cm1?

13

INCORRECT

A)a

B)b

C)c

D)d

==========

http://www.knockhardy.org.uk/sci_htm_files/mcspec.HTM

SPECTROSCOPY
MULTIPLE CHOICE QUESTIONS
1. The correct order for the basic features of a mass spectrometer is...

acceleration, deflection, detection, ionisation ionisation, acceleration, deflection, detection acceleration, ionisation, deflection, detection acceleration, deflection, ionisation, detection

2. Which one of the following statements about ionisation in a mass spectrometer is incorrect?

gaseous atoms are ionised by bombarding them with high energy electrons atoms are ionised so they can be accelerated atoms are ionised so they can be deflected it doesn't matter how much energy you use to ionise the atoms

3. The path of ions after deflection depends on...

only the mass of the ion only the charge on the ion both the charge and the mass of the ion neither the charge nor the mass of the ion

4. Which of the following species will be deflected to the greatest extent?


37

Na+ 35 Na+ 37 Na 35 Na2+

5. Which of the following is not a use for mass spectrometry?

calculating the isotopic abundance in elements investigating the elemental composition of planets confirming the presence of O-H and C=O in organic compounds calculating the molecular mass of organic compounds

6. Which one of the following statements about the mass spectrum of CH3Br is correct?

the last two peaks are of equal size and occur at m/z values of 94 and 96 the last two peaks have abundances in the ratio 3:1 and occur at m/z values of 94 and 96 there is just one peak for the molecular ion with an m/z value of 95 there is just one peak for the molecular ion with an m/z value of 44

7. Which one of the following pieces of information cannot be obtained from an infra-red spectrum?

the molecular mass the presence of C=O bonds the presence of O-H bonds the identity of a compound through comparison with other spectra

8. To check that a secondary alcohol has been completely oxidised to a ketone you can... check that the IR spectrum has absorptions at 3500cm-1 and 1650cm-1 check that the IR spectrum has no absorption around 3500cm-1 check that the IR spectrum has no absorption around 1650cm-1 check that the IR spectrum no absorptions at 3500cm-1 and 1650cm-1

9. The region of an infra-red spectrum where many absorptions take place is known as the...

thumbprint region handprint region footprint region fingerprint region

10. Proton nmr is useful for investigating the structure of organic compounds because...

organic compounds contain carbon atoms organic compounds are mostly covalent hydrogen atoms are found in nearly all organic compounds organic compounds have low boiling points

11. Which of the following statements about tetramethylsilane is incorrect? it produces a single peak at =10 it is inert it is volatile and can be easily distilled off and used again it is used to provide a reference against which other peaks are measured

12. Signals in a proton nmr spectrum do not provide information about...

the relative number of hydrogen atoms in a particular environment the number of chemically different hydrogen atoms on adjacent atoms the environment of different hydrogen atoms in a molecule the molecular mass of an organic molecule

13. The proton nmr spectrum of propane will consist of...

a triplet and a singlet a triplet and a quartet a doublet and a sextet a triplet and a septet

14. The proton nmr of 1-bromopropane will consist of...

two doublets and a sextet a doublet and a septet

a singlet, a doublet and a triplet two triplets and a sextet

15. The proton nmr of 2-bromopropane will consist of...

two doublets and a sextet a doublet and a septet a singlet, a doublet and a triplet a singlet, a doublet and a triplet

16. The proton nmr of 2-bromo-2-methylpropane will consist of...

three quartets and a singlet two doublets and a singlet two singlets one singlet

17. The splitting pattern for a signal is found by...

counting the number of chemically equivalent hydrogen atoms on adjacent atoms counting the number of chemically different hydrogen atoms on adjacent atoms counting the number of chemically different hydrogen atoms on adjacent atoms and adding 1 counting the number of chemically different hydrogen atoms on adjacent atoms and subtracting 1

18. Which one of the following statements about protons on O-H groups is incorrect?

they always produce a doublet they always produce a singlet they are not taken into account when working out splitting patterns of adjacent protons their signal can be removed from its normal location by shaking with deuterium oxide

19. The molecule HOCH2CH2OH will have an nmr spectrum consisting of...

two singlets a triplet and a doublet two doublets a singlet and a doublet

20. In a triplet, the relative peak areas are in the ratio...

1:1:1 1:2:1 1:3:1 1:4:1

21. Which compound has a molecular ion at m/z = 58, an infra red absorption at 1650cm-1 and just one singlet in its nmr spectrum?

butane CH3COCH3

CH3CH2CHO 2-methylpropane

22. Which one of the following hydrocarbons produces an nmr spectrum with more than one peak?

methane ethane butane cyclobutane


Correct; there are two peaks

23. The isomer of C4H8 which produces an nmr spectrum with four different signals is...

CH2=CHCH2CH3 CH3CH=CHCH3 it produces two signals (CH3)2C=CH2 it produces two signals cyclobutane it produces just one signal

24. To work out the molecular mass of an organic molecule you would look at its...

infra red spectrum mass spectrum proton nmr spectrum boiling point

25. Which one of the following methods would be best for finding the identity of an organic compound?

finding the m/z value of the molecular ion in its mass spectrum its proton nmr spectrum comparing its infra red spectrum with known examples measuring its melting point --------=================
PDF]

UNIT 12 NMR SPECTROSCOPY - Vedyadhara vedyadhara.ignou.ac.in/wiki/.../6/.../Unit_12_NMR_Spectrometry.pd... File Format: PDF/Adobe Acrobat - Quick View Representation of NMR. 12.7 Applications of NMR Spectroscopy. Quantitative Applications. Qualitative Applications. 12.8 Summary. 12.9 Terminal Questions ...

http://vedyadhara.ignou.ac.in/wiki/images/6/69/Unit_12_NMR_Spectrometry.pdf