Deck 13: Spectroscopy

Question 1

How many different types(sets) of hydrogens are there in 2,2-dimethylpentane?

A) 2
B) 3
C) 4
D) 5

Answer 1

4

Question 2

What is the multiplicity of the methylene hydrogens indicated in the proton NMR of the following compound?

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

Answer 2

singlet

Question 3

Which compound below fits the following proton NMR data?
Triplet $\quad$$\delta 1.22(3 \mathrm{H})$
Singlet $\quad$$\delta 1.98(3 \mathrm{H})$
Quartet $\quad$$\delta 4.07(2 \mathrm{H})$

A) A
B) B
C) C
D) D

Answer 3

B

Question 4

The proton NMR of 1,1-dibromoethane would appear as a

A) downfield doublet and upfield quartet.
B) downfield quartet and upfield doublet.
C) downfield doublet and upfield triplet.
D) downfield triplet and upfield doublet.

Question 5

A large doublet and a small septet pattern in ${ }^{1} \mathrm{H}$ NMR is usually indicative of a(n)

A) ethyl group.
B) propyl group.
C) isopropyl group.
D) phenyl group.

Question 6

Which of the following describes the spin-spin splitting of the indicated $\mathrm{H}$ in the ${ }^{1} \mathrm{H}$ NMR of the compound shown below?

A) singlet
B) doublet of doublets
C) triplet
D) doublet of triplets

Question 7

Identify the $\mathrm{C}_{4} \mathrm{H}_{9} \mathrm{Cl}$ isomer given the following proton NMR data:
Doublet $\quad \delta 1.04(6 \mathrm{H})$
Multiplet $\quad$$\delta 1.95(1 \mathrm{H})$
Doublet $\quad$$\delta 3.35(2 \mathrm{H})$

A)

B)

C)

D)

Question 8

Which of the compounds below fit the following C-13 NMR?

A) para-dichlorobenzene
B) meta-dichlorobenzene
C) ortho-dichlorobenzene
D) chlorobenzene

Question 9

A C-13 NMR spectrum of a compound, $\mathrm{C}_{10} \mathrm{H}_{14}$ , has five peaks. Two peaks are in the $10-30$ ppm region and the other three are in the 120-140 ppm area. Which of the following compounds fits the data?

A) I
B) II
C) III
D) IV

Question 10

Which one of the following has a $\lambda_{\max }$ in its UV-visible spectrum with the longest wavelength?

A)

B)

C)

D)

Question 11

The reaction shown below gave two products in a ratio of approximately $1: 2$ . The mass spectrum of the major product has a base peak at $\mathrm{m} / \mathrm{z} 119$ . The minor product gave a base peak at $\mathrm{m} / \mathrm{z} 133$ . Based on the reaction given and the information on the mass spectra, which of the following is the major product?

A) A
B) B
C) C
D) D

Question 12

Match each steroid below with its $\lambda_{\max }$ in its UV-visible spectrum.

A) A
B) B
C) C
D) D

Question 13

Which of the following compounds fits the proton NMR shown below?

A)

B)

C)

D)

Question 14

A compound, $\mathrm{C}_{20} \mathrm{H}_{30}$ , can be hydrogenated with platinum metal and hydrogen to give a compound $\mathrm{C}_{20} \mathrm{H}_{38}$ . How many double bonds (DB) and rings (R) does the original compound have? (The original compound has no triple bonds.)

A) $4 \mathrm{DB}, 2 \mathrm{R}$
B) $4 \mathrm{DB}, 1 \mathrm{R}$
C) $3 \mathrm{DB}, 3 \mathrm{R}$
D) $2 \mathrm{DB}, 4 \mathrm{R}$

Question 15

Determine the SODAR (sum of double bonds and rings) for a compound with the formula of $\mathrm{C}_{6} \mathrm{H}_{9} \mathrm{BrO}$ .

A) one
B) two
C) three
D) four