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Package Title: Solomons Test Bank Course Title: Solomons 11e Chapter Number: 9Question type: Multiple Choice How many signals would you expect to find in the 1 H NMR spectrum of CH 3 OCH 2 CH 2 OCH 3? A) 1 B) 2 C) 3 D) 4 E) 5Answer: BTopic: Proton NMR- Chemical Shift, Splitting, Etc. Section: 9. Dif...

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Package Title: Solomons Test Bank Course Title: Solomons 11e Chapter Number: 9

Question type: Multiple Choice 1) How many signals would you expect to find in the 1H NMR spectrum of CH3OCH2CH2OCH3? A) 1 B) 2 C) 3 D) 4 E) 5 Answer: B Topic: Proton NMR- Chemical Shift, Splitting, Etc. Section: 9.2 Difficulty Level: Easy

2) Predict the splitting pattern you would observe for the proton at C1 of 2,3-dimethyl-2phenylbutane.

A) Doublet B) Singlet C) Quartet D) Septet E) Octet Answer: B Topic: Proton NMR- Chemical Shift, Splitting, Etc. Section: 9.2 Difficulty Level: Easy

3) Which one of the following best represents the predicted approximate chemical shift and coupling for the hydrogen(s) indicated with the arrow?

1

O

CH3

A) 1.10 ppm, singlet B) 2.10 ppm, doublet C) 3.40 ppm, singlet D) 4.5 ppm, singlet E) 3.5 ppm, quartet Answer: C Topic: Proton NMR- Symmetry, Splitting, Chemical Shift Section: 9.2 Difficulty Level: Easy

4) Which one of the following best represents the predicted approximate chemical shift and coupling for the hydrogen(s) indicated with the arrow? O

A) 1.00 ppm, singlet B) 2.10 ppm, singlet C) 2.10 ppm, quartet D) 3.00 ppm, singlet E) 2.10 ppm, triplet Answer: B Topic: Proton NMR- Symmetry, Splitting, Chemical Shift Section: 9.2 Difficulty Level: Easy

5) Which one of the following best represents the predicted approximate chemical shift and coupling for the hydrogen(s) indicated with the arrow? O

A) 1.00 ppm, quartet B) 2.40 ppm, singlet C) 2.40 ppm, quartet D) 3.00 ppm, quartet

2

E) 2.40 ppm, triplet Answer: C Topic: Proton NMR- Symmetry, Splitting, Chemical Shift Section: 9.2 Difficulty Level: Easy

6) Which one of the following best represents the predicted approximate chemical shift and coupling for the hydrogen(s) indicated with the arrow? O

A) 1.00 ppm, quartet B) 2.40 ppm, singlet C) 2.40 ppm, quartet D) 3.00 ppm, quartet E) 1.00 ppm, triplet Answer: E Topic: Proton NMR- Symmetry, Splitting, Chemical Shift Section: 9.2 Difficulty Level: Easy

7) Which one of the following best represents the predicted approximate chemical shift and coupling for the hydrogen(s) indicated with the arrow in the compound nicotine?

A) 6.00 ppm, singlet B) 5.00 ppm. doublet C) 7.00 ppm, multiplet D) 9.00 ppm, triplet E) none of these choices Answer: C Topic: Proton NMR- Symmetry, Splitting, Chemical Shift

Section: 9.2 Difficulty Level: Easy

8) Which one of the following best represents the predicted approximate chemical shift and coupling for the hydrogen(s) indicated with the arrow in the compound nicotine?

A) 1.00 ppm, triplet B) 2.00 ppm, doublet C) 5.00 ppm, triplet D) 7.00 ppm. mulitplet E) None of these choices. Answer: C Topic: Proton NMR- Symmetry, Splitting, Chemical Shift Section: 9.2 Difficulty Level: Easy

9) Which one of the following best represents the predicted approximate chemical shift and coupling for the hydrogen(s) indicated with the arrow in the compound nicotine?

A) 1.00 ppm, singlet B) 2.00 ppm, doublet C) 3.00 ppm, broad multiplet D) 5.00 ppm, broad multiplet E) None of these choices. Answer: E Topic: Proton NMR- Symmetry, Splitting, Chemical Shift Section: 9.2 Difficulty Level: Easy 4

10) Which one of the following best represents the predicted approximate chemical shift and coupling for the hydrogen(s) indicated with the arrow? H

H

A) 5.40 ppm, multiplet B) 2.00 ppm, multiplet C) 2.00 ppm, doublet D) 2.00 ppm, quartet E) 5.40 ppm, doublet Answer: A Topic: Proton NMR- Symmetry, Splitting, Chemical Shift Section: 9.2 Difficulty Level: Easy

11) Which one of the following best represents the predicted approximate chemical shift and coupling for the hydrogen(s) indicated with the arrow? H

H

A) 5.40 ppm, doublet B) 1.00 ppm, multiplet C) 2.00 ppm, doublet D) 1.00 ppm, doublet E) 5.40 ppm, multiplet Answer: D Topic: Proton NMR- Symmetry, Splitting, Chemical Shift Section: 9.2 Difficulty Level: Easy

12) Which one of the following best represents the predicted approximate chemical shift and coupling for the hydrogen(s) indicated with the arrow? N

A) 3.00 ppm, doublet B) 3.00 ppm, triplet C) 5.00 ppm, triplet D) 1.00 ppm, doublet E) 5.40 ppm, multiplet Answer: B Topic: Proton NMR- Symmetry, Splitting, Chemical Shift Section: 9.2 Difficulty Level: Easy

13) Which one of the following best represents the predicted approximate chemical shift and coupling for the hydrogen(s) indicated with the arrow? N

A) 3.00 ppm, doublet B) 3.00 ppm, triplet C) 5.00 ppm, triplet D) 1.00 ppm, doublet E) 3.00 ppm, singlet Answer: E Topic: Proton NMR- Symmetry, Splitting, Chemical Shift Section: 9.2 Difficulty Level: Easy

14) For the following compound how many different signals would you see in the proton NMR? (Assume that you can see them all.)

A) 4 B) 5 C) 6 D) 7 E) 8 Answer: A Topic: Proton NMR- Symmetry, Splitting, Chemical Shift Section: 9.2 6

Difficulty Level: Easy

15) For the compound dimedone, how many different signals would you see in the proton NMR? (Assume that you can see them all.)

A) 2 B) 3 C) 4 D) 5 E) None of these choices. Answer: B Topic: Proton NMR- Symmetry, Splitting, Chemical Shift Section: 9.2 Difficulty Level: Easy

16) For the following compound how many different signals would you see in the proton NMR? (Assume that you can see them all.) H3 CO

A) 4 B) 5 C) 6 D) 7 E) 8 Answer: C Topic: Proton NMR- Symmetry, Splitting, Chemical Shift Section: 9.2 Difficulty Level: Easy

17) For the following compound how many different signals would you see in the proton NMR? (Assume that you can see them all.)

A) 1 B) 2 C) 3 D) 4 E) 5 Answer: C Topic: Proton NMR- Symmetry, Splitting, Chemical Shift Section: 9.2 Difficulty Level: Easy

18) For the compound adamantine, how many different signals would you see in the proton NMR? (Assume that you can see them all.)

A) 1 B) 2 C) 3 D) 4 E) None of these choices. Answer: B Topic: Proton NMR- Symmetry, Splitting, Chemical Shift Section: 9.2 Difficulty Level: Easy 19) A downfield ( 9-10) singlet is observed in the 1H NMR spectrum of: O

A) CH3CCH2 CH 3 H

B) C6H5CH2C

O

H

C) (CH3)2CHC

O

8

H

D) (CH3)3CC

O

O

E) C6H 5CH2 CCH3 Answer: D Topic: Proton NMR- Symmetry, Splitting, Chemical Shift Section: 9.2 Difficulty Level: Easy

20) For the following compound how many different signals would you see in the proton NMR? (Assume that you can see them all.)

A) 1 B) 2 C) 3 D) 4 E) 5 Answer: D Topic: Proton NMR- Symmetry, Splitting, Chemical Shift Section: 9.2 Difficulty Level: Medium

22) For the following compound how many different signals would you see in the proton NMR? (Assume that you can see them all.)

O

A) 4 B) 5 C) 6 D) 7 E) 8 Answer: B Topic: Proton NMR- Symmetry, Splitting, Chemical Shift

Section: 9.2 Difficulty Level: Medium

23) Which one of the following best represents the predicted approximate chemical shift and coupling for the hydrogen(s) indicated with the arrow? O

CH3

A) 1.10 ppm, singlet B) 2.10 ppm, triplet C) 3.40 ppm, triplet D) 4.5 ppm, singlet E) 5.3 ppm, doublet Answer: D Topic: Proton NMR- Symmetry, Splitting, Chemical Shift Section: 9.2 Difficulty Level: Medium

24) Predict the splitting pattern you would observe for the proton at C4 of 2,3-dimethyl-2phenylbutane.

A) Doublet B) Singlet C) Quartet D) Septet E) Octet Answer: A Topic: Proton NMR- Chemical Shift, Splitting, Etc. Section: 9.2 Difficulty Level: Medium 25) How many 1H NMR signals would trans-1,2-dichlorocyclopropane give? A) 1 B) 2 C) 3 10

D) 4 E) 5 Answer: C Topic: Proton NMR- Chemical Shift, Splitting, Etc. Section: 9.2 Difficulty Level: Medium 26) How many chemically distinct 1H NMR signals are there in the following compound? ClCH2 CHCH3 Br

A) 1 B) 2 C) 3 D) 4 E) 5 Answer: D Topic: Proton NMR- Chemical Shift, Splitting, Etc. Section: 9.2 Difficulty Level: Medium 27) How many 1H NMR signals would cis-1,2-dichlorocyclopropane give? A) 1 B) 2 C) 3 D) 4 E) 5 Answer: CB Topic: Proton NMR- Chemical Shift, Splitting, Etc. Section: 9.2 Difficulty Level: Medium 28) How many 1H NMR signals would you expect from this compound?

OCH 3

OCH 3

A) 1 B) 2 C) 3 D) 4 E) 5 Answer: B Topic: Proton NMR- Chemical Shift, Splitting, Etc. Section: 9.2 Difficulty Level: Medium 29) The 1H NMR spectrum of which of these compounds would consist of a triplet, singlet and quartet only? A) 2-chloro-4-methylpentane B) 3-chloro-2-methylpentane C) 3-chloropentane D) 1-chloro-2,2-dimethylbutane E) 3-chloro-3-methylpentane Answer: E Topic: Proton NMR- Chemical Shift, Splitting, Etc. Section: 9.2 Difficulty Level: Medium

30) Which one of the following best represents the predicted approximate chemical shift and coupling for the hydrogen(s) indicated with the arrow? H

H

A) 1.00 ppm, doublet B) 2.00 ppm, singlet C) 2.00 ppm, triplet D) 2.00 ppm, doublet E) 1.00 ppm, triplet

12

Answer: D Topic: Proton NMR- Symmetry, Splitting, Chemical Shift Section: 9.2 Difficulty Level: Medium

31) Which of the following compounds would not be represented by a lone singlet in the proton NMR? A) cyclohexane B) benzene C) dimethyl ether (CH3-O-CH3) D) 1,2-ethanediol E) none of these choices Answer: D Topic: Proton NMR- Symmetry, Splitting, Chemical Shift Section: 9.2 Difficulty Level: Medium 32) A compound C5H11Cl which exhibits only two singlets in the 1H NMR spectrum must be: A) 1-Chloropentane B) 1-Chloro-2,2-dimethylpropane C) 1-Chloro-2-methylbutane D) 3-Chloropentane E) 1-Chloro-3-methylbutane Answer: B Topic: Proton NMR- Symmetry, Splitting, Chemical Shift Section: 9.2 Difficulty Level: Medium 33) A compound that would show two triplets and a septet in the 1H NMR spectrum could be: A) 3-ethylpentane B) 2-bromopropane C) chlorocyclopropane D) 1-iodopropane E) none of these choices Answer: C

Topic: Proton NMR- Symmetry, Splitting, Chemical Shift Section: 9.2 Difficulty Level: Medium 34) Consider the expected 1H NMR spectrum of 1,1,3,3-tetramethylcyclopentane. Which of the following is likely to be observed?

A) 7 signals: all singlets B) 7 signals: 4 singlets, 3 doublets C) 3 signals: all singlets D) 3 signals: one singlet, 2 doublets E) 3 signals: two singlets, one doublet Answer: C Topic: Proton NMR- Symmetry, Splitting, Chemical Shift Section: 9.2 Difficulty Level: Medium 35) Consider the expected 1H NMR spectrum of 2,4-dimethyl-1,4-pentadiene. Which of the following is likely to be observed?

A) 7 signals: all singlets B) 4 signals: all singlets C) 3 signals: all singlets D) 3 signals: one singlet, 2 doublets E) 4 signals: two singlets, two doublets Answer: E Topic: Proton NMR- Symmetry, Splitting, Chemical Shift Section: 9.2 Difficulty Level: Medium 36) The 1H NMR signal for which of the indicated protons will occur at the lowest frequency (most upfield signal)?

14

A) I B) II C) III D) IV E) V Answer: A Topic: Proton NMR- Symmetry, Splitting, Chemical Shift Section: 9.2 Difficulty Level: Medium

37) If all the protons of 1-fluoropentane could be discerned, which would you expect to be at the lowest field in the 1H NMR spectrum of this compound? CH3 CH 2CH2 CH2 CH2 F V IV III II

I

A) Protons on carbon I B) Protons on carbon II C) Protons on carbon III D) Protons on carbon IV E) Protons on carbon V Answer: A Topic: Proton NMR- Chemical Shift, Splitting, Etc. Section: 9.2 Difficulty Level: Easy 38. The 1H NMR signal for which of the indicated protons occurs farthest downfield?

III Cl H H

C C C

C CH 3

I

H

IV

II V

A) I B) II C) III D) IV E) V Answer: E Topic: Proton NMR- Chemical Shift, Splitting, Etc. Section: 9.2 Difficulty Level: Hard 39) Which proton(s) of the compound below would appear as a septet in the 1H NMR spectrum? I CH3 CH3CH2CH2-O-CH CH3 II V IV III I A) The protons on carbon I B) The protons on carbon II C) The protons on carbon III D) The protons on carbon IV E) The protons on carbon V Answer: B Topic: Proton NMR- Chemical Shift, Splitting, Etc. Section: 9.2 Difficulty Level: Easy 40) Which proton(s) of the compound below would appear as a doublet in the 1H NMR spectrum? I CH3 CH3CH2CH2-O-CH CH3 V IV III II I

16

A) The protons on carbon I. B) The protons on carbon II. C) The protons on carbon III. D) The protons on carbon IV. E) The protons on carbon V. Answer: A Topic: Proton NMR- Chemical Shift, Splitting, Etc. Section: 9.2 Difficulty Level: Easy 41) Which proton(s) of the compound below would appear as a triplet in the 1H NMR spectrum? I CH3 CH3CH2CH2-O-CH CH3 II V IV III I A) The protons on carbon II. B) The protons on carbon I and V. C) The protons on carbon III and V. D) The protons on carbon III and IV. E) The protons on carbon V. Answer: C Topic: Proton NMR- Chemical Shift, Splitting, Etc. Section: 9.2 Difficulty Level: Easy

42) Predict the splitting pattern you would observe for the proton at C3 of 2,3-dimethyl-2phenylbutane.

A) Doublet B) Singlet C) Quartet D) Septet E) Octet Answer: D Topic: Proton NMR- Chemical Shift, Splitting, Etc.

Section: 9.2 Difficulty Level: Medium 43) Which of these compounds will not be represented by a singlet only in the 1H NMR spectrum? A) Neopentane B) Hexamethylbenzene C) Isobutane D) (Z)-1,2-Dichloroethene E) (E)-1,2-Dichloroethene Answer: C Topic: Proton NMR- Symmetry, Splitting, Chemical Shift Section: 9.2 Difficulty Level: Medium 44) Consider the expected splitting of the C2 proton signal in the 1H NMR spectrum of 1,1dibromopentane. Presuming that the coupling constants for neighboring protons are sufficiently different, and that the instrument has sufficient resolving power, what is the theoretical multiplicity of the C2 proton signal? A) 3 B) 4 C) 5 D) 6 E) 8 Answer: D Topic: Proton NMR- Symmetry, Splitting, Chemical Shift Section: 9.2 Difficulty Level: Hard 45) Consider the expected splitting of the C2 proton signal in the 1H NMR spectrum of 2-ethyl1,3-propanediol. Presuming that the coupling constants for neighboring protons are sufficiently different, and that the instrument has sufficient resolving power, what is the theoretical multiplicity of the C2 proton signal? A) 6 B) 7 C) 8 D) 12 E) 15

18

Answer: E Topic: Proton NMR- Symmetry, Splitting, Chemical Shift Section: 9.2 Difficulty Level: Hard 46) What is the theoretical multiplicity of the C-2 proton signal in the 1H NMR spectrum of 2hydroxymethyl-1,3-propanediol, shown below? OH HO

OH

A) 1 B) 6 C) 7 D) 8 E) 9 Answer: C Topic: Proton NMR- Symmetry, Splitting, Chemical Shift Section: 9.2 Difficulty Level: Hard 47) Consider the 1H NMR spectrum of very pure 1-propanol. Assuming the maximum multiplicity of signals and non-superposition of peaks, what is the expected signal splitting pattern for each signal, in the order (a, b, c, d) ? CH3-CH2-CH2-OH a b c d

A) 3, 6, 4, 1 B) 3, 6, 4, 3 C) 3, 12, 3, 1 D) 3, 12, 3, 3 E) 3, 12, 6, 3 Answer: E Topic: Proton NMR- Chemical Shift, Splitting, Etc. Section: 9.2 Difficulty Level: Hard

48) The 1H NMR spectrum of which of the compounds below, all of formula C7H12O2, would O

O

O O

O

I

II O

III O

O

O

IV

consist of two singlets only?

V

A) I B) II C) III D) IV E) V Answer: E Topic: Proton NMR- Chemical Shift, Splitting, Etc. Section: 9.2, 9.2 Difficulty Level: Medium 49) The 1H NMR spectrum of which of the compounds below, all of formula C7H12O2, would consist of three singlets only? O

O

O O

O

I

II O

III O

O

O

IV

V

A) I B) II C) III D) IV E) V Answer: B Topic: Proton NMR- Chemical Shift, Splitting, Etc. Section: 9.2, 9.2 Difficulty Level: Hard

20

O

O

50) The 1H NMR spectrum of which of the compounds below, all of formula C7H12O2, would consist of a singlet, a doublet and a triplet only? O

O

O O

O

O

I

II O

III O

O

O

IV

V

A) I B) II C) III D) IV E) V Answer: D Topic: Proton NMR- Chemical Shift, Splitting, Etc. Section: 9.2, 9.2 Difficulty Level: Hard 51) A compound with the molecular formula C4H10O gives a 1H NMR spectrum consisting only of a quartet centered at 3.5 and a triplet at  1.1. The most likely structure for the compound is: CH3 CH3COH

A)

CH3 CH3

B) CH 3OCHOH C) CH3CH2CH2CH2OH D) CH3CH2OCH2CH3 CH 3CHCH2OH

E)

CH 3

Answer: D Topic: Proton NMR- Unknown Identification Section: 9.2, 9.2, 9.2

Difficulty Level: Medium 52) What is the structure of the compound in the following 1H-NMR spectrum with the molecular formula C9H10O2? Relative integration is shown.

5 2 2 1

12

10

8

6

4

2

0

PPM

CHO

A) CO2 H

B) CO2 H

C)

D) HO2C CO2H

E) Answer: C Topic: Proton NMR- Unknown Identification Section: 9.2, 9.3 Difficulty Level: Easy 53) What is the structure of the compound in the following 1H-NMR spectrum with the molecular formula C8H14? Relative integration is shown.

22

9

3 2

8

7

6

5

4 PPM

3

2

1

0

A) B) C

C)

D)

E) Answer: D Topic: Proton NMR- Unknown Identification Section: 9.2, 9.3 Difficulty Level: Easy 54) What is the structure of the compound in the following 1H-NMR spectrum with the molecular formula C6H11N? In the IR spectrum you notice a stretch at about 2250 cm-1. Relative integration is shown.

CN

A)

B) CN

C) CN

D) N

H E) Answer: D

Topic: Proton NMR- Unknown Identification Section: 9.2, 9.3 Difficulty Level: Easy

55) Determine the most likely structure of a compound, with the molecular formula C9H12, which gave a 1H NMR spectrum consisting of: a doublet at  1.25 a septet at  2.90 and a multiplet at  7.25

24

I

II

III

IV

V ]

A) I B) II C) III D) IV E) V Answer: D Topic: Proton NMR- Unknown Identification Section: 9.2, 9.3 Difficulty Level: Medium 56) A compound with the molecular formula C10H13Cl gave the following 1H NMR spectrum: singlet,  1.6 singlet,  3.1 multiplet,  7.2 (5H) The most likely structure for the compound is: Cl

I

Cl

Cl

II

III Cl

Cl

IV

V

A) I B) II C) III D) IV E) V Answer: B Topic: Proton NMR- Unknown Identification Section: 9.2, 9.3 Difficulty Level: Medium 57) A compound with the molecular formula C8H9BrO gave the following 1H NMR spectrum: triplet,  1.4 quartet,  3.9

multiplet,  7.0 (4H) There was no evidence of an -OH band in the IR spectrum. A possible structure for the compound is: O
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