Multiple Choice Quiz

Multiple Choice Quiz

Multiple Choice Quiz

1

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.

2

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

3

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.

4

Which of the following compounds has the MOST deshielded protons?

A)

CH₃Cl

B)

CH₃I

C)

CH₃Br

D)

CH₄

5

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

A)

tetramethylsilane

B)

methyl fluoride

C)

methanol

D)

methylamine

6

What is the value of the chemical shift δ 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

7

The chemical shift of the protons in acetone is δ2.06. 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

8

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

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

9

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

<a onClick="window.open('/olcweb/cgi/pluginpop.cgi?it=jpg::::/sites/dl/free/0072397462/209343/15_9.jpg','popWin', 'width=NaN,height=NaN,resizable,scrollbars');" href="#"><img valign="absmiddle" height="16" width="16" border="0" src="/olcweb/styles/shared/linkicons/image.gif"> (13.0K)</a>

A)

5

B)

1

C)

6

D)

8

10

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

A)

<a onClick="window.open('/olcweb/cgi/pluginpop.cgi?it=jpg::::/sites/dl/free/0072397462/209343/15_10a.jpg','popWin', 'width=NaN,height=NaN,resizable,scrollbars');" href="#"><img valign="absmiddle" height="16" width="16" border="0" src="/olcweb/styles/shared/linkicons/image.gif"> (11.0K)</a>

B)

<a onClick="window.open('/olcweb/cgi/pluginpop.cgi?it=jpg::::/sites/dl/free/0072397462/209343/15_10b.jpg','popWin', 'width=NaN,height=NaN,resizable,scrollbars');" href="#"><img valign="absmiddle" height="16" width="16" border="0" src="/olcweb/styles/shared/linkicons/image.gif"> (10.0K)</a>

C)

<a onClick="window.open('/olcweb/cgi/pluginpop.cgi?it=jpg::::/sites/dl/free/0072397462/209343/15_10c.jpg','popWin', 'width=NaN,height=NaN,resizable,scrollbars');" href="#"><img valign="absmiddle" height="16" width="16" border="0" src="/olcweb/styles/shared/linkicons/image.gif"> (12.0K)</a>

D)

<a onClick="window.open('/olcweb/cgi/pluginpop.cgi?it=jpg::::/sites/dl/free/0072397462/209343/15_10d.jpg','popWin', 'width=NaN,height=NaN,resizable,scrollbars');" href="#"><img valign="absmiddle" height="16" width="16" border="0" src="/olcweb/styles/shared/linkicons/image.gif"> (13.0K)</a>

11

How many nonequivalent protons does the following structure have?

<a onClick="window.open('/olcweb/cgi/pluginpop.cgi?it=jpg::::/sites/dl/free/0072397462/209343/15_11.jpg','popWin', 'width=NaN,height=NaN,resizable,scrollbars');" href="#"><img valign="absmiddle" height="16" width="16" border="0" src="/olcweb/styles/shared/linkicons/image.gif"> (12.0K)</a>

A)

12

B)

8

C)

6

D)

4

12

How many nonequivalent protons does the following structure have?

<a onClick="window.open('/olcweb/cgi/pluginpop.cgi?it=jpg::::/sites/dl/free/0072397462/209343/15_12.jpg','popWin', 'width=NaN,height=NaN,resizable,scrollbars');" href="#"><img valign="absmiddle" height="16" width="16" border="0" src="/olcweb/styles/shared/linkicons/image.gif"> (12.0K)</a>

A)

6

B)

5

C)

4

D)

3

13

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

<a onClick="window.open('/olcweb/cgi/pluginpop.cgi?it=jpg::::/sites/dl/free/0072397462/209343/15_13.jpg','popWin', 'width=NaN,height=NaN,resizable,scrollbars');" href="#"><img valign="absmiddle" height="16" width="16" border="0" src="/olcweb/styles/shared/linkicons/image.gif"> (13.0K)</a>

A)

2

B)

3

C)

4

D)

5

14

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?

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A)

s, s, s

B)

d, d, s

C)

s, d, d

D)

s, s, d

15

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

A)

triplet

B)

quartet

C)

doublet

D)

septet

16

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

A)

doublet.

B)

triplet.

C)

quartet.

D)

quintet.

17

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

<a onClick="window.open('/olcweb/cgi/pluginpop.cgi?it=jpg::::/sites/dl/free/0072397462/209343/15_17.jpg','popWin', 'width=NaN,height=NaN,resizable,scrollbars');" href="#"><img valign="absmiddle" height="16" width="16" border="0" src="/olcweb/styles/shared/linkicons/image.gif"> (16.0K)</a>

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

Propose a structure for the following compound.
¹H NMR spectrum of C₅H₈O₂:
δ 1.90 (multiplet, 4H)
δ2.40 (triplet, 2H)
δ 4.26 (triplet, 2H)

A)

<a onClick="window.open('/olcweb/cgi/pluginpop.cgi?it=jpg::::/sites/dl/free/0072397462/209343/15_18a.jpg','popWin', 'width=NaN,height=NaN,resizable,scrollbars');" href="#"><img valign="absmiddle" height="16" width="16" border="0" src="/olcweb/styles/shared/linkicons/image.gif"> (12.0K)</a>

B)

<a onClick="window.open('/olcweb/cgi/pluginpop.cgi?it=jpg::::/sites/dl/free/0072397462/209343/15_18b.jpg','popWin', 'width=NaN,height=NaN,resizable,scrollbars');" href="#"><img valign="absmiddle" height="16" width="16" border="0" src="/olcweb/styles/shared/linkicons/image.gif"> (13.0K)</a>

C)

<a onClick="window.open('/olcweb/cgi/pluginpop.cgi?it=jpg::::/sites/dl/free/0072397462/209343/15_18c.jpg','popWin', 'width=NaN,height=NaN,resizable,scrollbars');" href="#"><img valign="absmiddle" height="16" width="16" border="0" src="/olcweb/styles/shared/linkicons/image.gif"> (12.0K)</a>

D)

<a onClick="window.open('/olcweb/cgi/pluginpop.cgi?it=jpg::::/sites/dl/free/0072397462/209343/15_18d.jpg','popWin', 'width=NaN,height=NaN,resizable,scrollbars');" href="#"><img valign="absmiddle" height="16" width="16" border="0" src="/olcweb/styles/shared/linkicons/image.gif"> (12.0K)</a>

19

Which ¹H NMR spectrum represents the following compound?

<a onClick="window.open('/olcweb/cgi/pluginpop.cgi?it=jpg::::/sites/dl/free/0072397462/209343/15_19.jpg','popWin', 'width=NaN,height=NaN,resizable,scrollbars');" href="#"><img valign="absmiddle" height="16" width="16" border="0" src="/olcweb/styles/shared/linkicons/image.gif"> (13.0K)</a>

A)

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

B)

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

C)

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

D)

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

20

An unknown compound A has the molecular formula C₄H₈O₂. Based on the following ¹H NMR spectrum, what is the structure of compound A?

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A)

<a onClick="window.open('/olcweb/cgi/pluginpop.cgi?it=jpg::::/sites/dl/free/0072397462/209343/15_20a.jpg','popWin', 'width=NaN,height=NaN,resizable,scrollbars');" href="#"><img valign="absmiddle" height="16" width="16" border="0" src="/olcweb/styles/shared/linkicons/image.gif"> (12.0K)</a>

B)

<a onClick="window.open('/olcweb/cgi/pluginpop.cgi?it=jpg::::/sites/dl/free/0072397462/209343/15_20b.jpg','popWin', 'width=NaN,height=NaN,resizable,scrollbars');" href="#"><img valign="absmiddle" height="16" width="16" border="0" src="/olcweb/styles/shared/linkicons/image.gif"> (12.0K)</a>

C)

<a onClick="window.open('/olcweb/cgi/pluginpop.cgi?it=jpg::::/sites/dl/free/0072397462/209343/15_20c.jpg','popWin', 'width=NaN,height=NaN,resizable,scrollbars');" href="#"><img valign="absmiddle" height="16" width="16" border="0" src="/olcweb/styles/shared/linkicons/image.gif"> (11.0K)</a>

D)

<a onClick="window.open('/olcweb/cgi/pluginpop.cgi?it=jpg::::/sites/dl/free/0072397462/209343/15_20d.jpg','popWin', 'width=NaN,height=NaN,resizable,scrollbars');" href="#"><img valign="absmiddle" height="16" width="16" border="0" src="/olcweb/styles/shared/linkicons/image.gif"> (12.0K)</a>

21

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

<a onClick="window.open('/olcweb/cgi/pluginpop.cgi?it=jpg::::/sites/dl/free/0072397462/209343/15_21.jpg','popWin', 'width=NaN,height=NaN,resizable,scrollbars');" href="#"><img valign="absmiddle" height="16" width="16" border="0" src="/olcweb/styles/shared/linkicons/image.gif"> (23.0K)</a>

A)

<a onClick="window.open('/olcweb/cgi/pluginpop.cgi?it=jpg::::/sites/dl/free/0072397462/209343/15_21a.jpg','popWin', 'width=NaN,height=NaN,resizable,scrollbars');" href="#"><img valign="absmiddle" height="16" width="16" border="0" src="/olcweb/styles/shared/linkicons/image.gif"> (14.0K)</a>

B)

<a onClick="window.open('/olcweb/cgi/pluginpop.cgi?it=jpg::::/sites/dl/free/0072397462/209343/15_21b.jpg','popWin', 'width=NaN,height=NaN,resizable,scrollbars');" href="#"><img valign="absmiddle" height="16" width="16" border="0" src="/olcweb/styles/shared/linkicons/image.gif"> (14.0K)</a>

C)

<a onClick="window.open('/olcweb/cgi/pluginpop.cgi?it=jpg::::/sites/dl/free/0072397462/209343/15_21c.jpg','popWin', 'width=NaN,height=NaN,resizable,scrollbars');" href="#"><img valign="absmiddle" height="16" width="16" border="0" src="/olcweb/styles/shared/linkicons/image.gif"> (14.0K)</a>

D)

<a onClick="window.open('/olcweb/cgi/pluginpop.cgi?it=jpg::::/sites/dl/free/0072397462/209343/15_21d.jpg','popWin', 'width=NaN,height=NaN,resizable,scrollbars');" href="#"><img valign="absmiddle" height="16" width="16" border="0" src="/olcweb/styles/shared/linkicons/image.gif"> (14.0K)</a>

22

A compound of formula C₅H₁₂ gives 1 signal in the ¹H NMR and 2 signals in the ¹³C NMR. The compound is

A)

pentane.

B)

2-methylbutane.

C)

2,2-dimethylpropane.

D)

Cannot tell without more information.

23

There are several compounds with the molecular formula C₅H₁₀Br₂. Which isomer a–d with this formula has the following ¹H NMR spectrum?

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

<a onClick="window.open('/olcweb/cgi/pluginpop.cgi?it=jpg::::/sites/dl/free/0072397462/209343/15_22.jpg','popWin', 'width=NaN,height=NaN,resizable,scrollbars');" href="#"><img valign="absmiddle" height="16" width="16" border="0" src="/olcweb/styles/shared/linkicons/image.gif"> (18.0K)</a>

A)

a

B)

b

C)

c

D)

d

24

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

25

How many absorption bands will appear in the ¹³C NMR spectrum for the following compound?

<a onClick="window.open('/olcweb/cgi/pluginpop.cgi?it=jpg::::/sites/dl/free/0072397462/209343/15_23.jpg','popWin', 'width=NaN,height=NaN,resizable,scrollbars');" href="#"><img valign="absmiddle" height="16" width="16" border="0" src="/olcweb/styles/shared/linkicons/image.gif"> (14.0K)</a>

A)

4

B)

6

C)

7

D)

8

26

How many absorption bands will appear in the ¹³C NMR spectrum for the following compound?

<a onClick="window.open('/olcweb/cgi/pluginpop.cgi?it=jpg::::/sites/dl/free/0072397462/209343/15_24.jpg','popWin', 'width=NaN,height=NaN,resizable,scrollbars');" href="#"><img valign="absmiddle" height="16" width="16" border="0" src="/olcweb/styles/shared/linkicons/image.gif"> (12.0K)</a>

A)

6

B)

7

C)

8

D)

9

27

How many absorption bands will appear in the ¹³C NMR spectrum for the following compound?

<a onClick="window.open('/olcweb/cgi/pluginpop.cgi?it=jpg::::/sites/dl/free/0072397462/209343/15_25.jpg','popWin', 'width=NaN,height=NaN,resizable,scrollbars');" href="#"><img valign="absmiddle" height="16" width="16" border="0" src="/olcweb/styles/shared/linkicons/image.gif"> (14.0K)</a>

A)

5

B)

7

C)

8

D)

9

28

How many resonances in the ¹³C NMR spectrum would the following structure show?

<a onClick="window.open('/olcweb/cgi/pluginpop.cgi?it=jpg::::/sites/dl/free/0072397462/209343/15_26.jpg','popWin', 'width=NaN,height=NaN,resizable,scrollbars');" href="#"><img valign="absmiddle" height="16" width="16" border="0" src="/olcweb/styles/shared/linkicons/image.gif"> (14.0K)</a>

A)

8

B)

6

C)

4

D)

2

29

How many signals are expected in a ¹³C NMR spectrum of methylcyclohexane?

A)

4

B)

5

C)

6

D)

7

30

Deduce the structure of an unknown compound using the following ¹H NMR spectrum, mass spectroscopy data, and IR spectrum.
¹H NMR spectrum:
δ1.30 (triplet, 6H)
δ4.29 (quartet, 4H)
δ 7.4–7.9 (multiplet, 4H)

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

IR Spectrum:
Intensity (peak):	Frequency (cm^–1):
s	3100
m	2900
m	2800
s	1740
m-w	1600
m-w	1475
m	1465
m	1450
m	1375
s	1300–1000

A)

<a onClick="window.open('/olcweb/cgi/pluginpop.cgi?it=jpg::::/sites/dl/free/0072397462/209343/15_27a.jpg','popWin', 'width=NaN,height=NaN,resizable,scrollbars');" href="#"><img valign="absmiddle" height="16" width="16" border="0" src="/olcweb/styles/shared/linkicons/image.gif"> (18.0K)</a>

B)

<a onClick="window.open('/olcweb/cgi/pluginpop.cgi?it=jpg::::/sites/dl/free/0072397462/209343/15_27b.jpg','popWin', 'width=NaN,height=NaN,resizable,scrollbars');" href="#"><img valign="absmiddle" height="16" width="16" border="0" src="/olcweb/styles/shared/linkicons/image.gif"> (15.0K)</a>

C)

<a onClick="window.open('/olcweb/cgi/pluginpop.cgi?it=jpg::::/sites/dl/free/0072397462/209343/15_27c.jpg','popWin', 'width=NaN,height=NaN,resizable,scrollbars');" href="#"><img valign="absmiddle" height="16" width="16" border="0" src="/olcweb/styles/shared/linkicons/image.gif"> (13.0K)</a>

D)

<a onClick="window.open('/olcweb/cgi/pluginpop.cgi?it=jpg::::/sites/dl/free/0072397462/209343/15_27d.jpg','popWin', 'width=NaN,height=NaN,resizable,scrollbars');" href="#"><img valign="absmiddle" height="16" width="16" border="0" src="/olcweb/styles/shared/linkicons/image.gif"> (17.0K)</a>

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