Chapter 9 Pretest Questions 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

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

3) 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, doublet C) 3.40 ppm, singlet D) 4.5 ppm, singlet E) 3.5 ppm, quartet 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 3.00 ppm, quartet

B) 2.40 ppm, singlet E) 2.40 ppm, triplet

C) 2.40 ppm, quartet

D)

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 1

D) 7

E) 8

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
O

B) 2
H

C) 3

D) 4
H H O

19) A downfield ( 9-10) singlet is observed in the 1H NMR spectrum of: A) CH3CCH2CH3 B) C6H5CH2C
O

C) (CH3)2CHC

D) (CH3)3CC

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

25) How many 1H NMR signals would trans-1,2-dichlorocyclopropane give? A) 1 B) 2 C) 3 D) 4 E) 5

28) How many 1H NMR signals would you expect from this compound?
OCH3

OCH3

A) 1

B) 2

C) 3

D) 4

E) 5

29) The 1H NMR spectrum of which of these compounds would consist of a triplet, singlet and quartet only? (hint: no C-H sec carbon) A) 2-chloro-4-methylpentane B) 3-chloro-2-methylpentane C) 3-chloropentane D) 1-chloro-2,2-dimethylbutane E) 3-chloro-3-methylpentane

30) Which one of the following best represents the predicted approximate chemical shift and coupling for the hydrogen(s) indicated with the arrow?
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 38. The 1H NMR signal for which of the indicated protons occurs farthest downfield?
Cl H C C C H H

III IV V

I II

C CH3

A) I

B) II

C) III

D) IV

E) V

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

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

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 1 2

12

10

PPM

CHO

CO2H

A)
CO2H

B)

C)
CO2H

D) HO2C

E) 85) Consider the expected splitting of signal b in the 1H NMR spectrum of 1,1-dichloro-3methylbutane, shown below. Presuming that Jab is sufficiently different from Jbc and that the instrument has sufficient resolving power, what is the theoretical multiplicity of signal b? Cl a
a b c d
Cl

A) 8

B) 9

C) 12

D) 18

E) 21

111) Which compound below would give rise to 5 signals in the proton NMR spectrum and 7 signals in the carbon NMR spectrum? (Assume you can separate and see all peaks.)
Br

II

III

IV

A) I

B) II

C) III

D) IV

E) None of these choices.

114) What is the structure of the compound in the following 1H-NMR spectrum with the molecular formula C6H10O2? The 13C-NMR shows characteristic chemical shifts at 22.3, 31.1, 117.3, 157.7, and 171.6 ppm. Relative integration is shown.

1 exchanges w/ D2O 1 1 1

13

12

11

10

PPM

CO2H
HO O

A)
CO2H

B)
CO2H

C)

D) 118) Which is the base peak?

E)

A) 15

B) 29

C) 44

D) 45

E) 100

119) Which is the likely molecular ion (M)?

A) 15

B) 29

C) 44

D) 45

E) 100

152) An unknown compound, F, has the formula C3H6O2. Elucidate the structure of F by scrutinizing its IR, 1H NMR and 13C NMR spectra, shown below.