Dr.

Manashi Chatterjee Week-2-Recitation

Chem-224

A compound with the molecular formula C8Hl8, produces a single NMR

signal. What is its structural formula?
A . CH3(CH2)6CH3
B . (CH3)2CHCH2(CH2)3CH3
C . (CH3)2CHCH2CH(CH3)CH2CH3
D . (CH3)3CC(CH3)3
Indicate if the protons in bold are Homotopic, Enantiotopic or Diastereotopic and if they
must appear at the same chemical shift in proton NMR or not. Circle the correct answer.
Dr. Manashi Chatterjee Week-2-Recitation
Chem-224

For each set of compounds below, circle the one in which the indicated hydrogen is
furthest upfield in a 1H NMR spectrum.
Dr. Manashi Chatterjee Week-2-Recitation
Chem-224

Write the number of chemically non-equivalent (number of different types) of hydrogens

and carbons in the appropriate boxes below
Dr. Manashi Chatterjee Week-2-Recitation
Chem-224

Give the number of expected signals (ignore splitting) in 1H and 13C NMR (proton
decoupled) spectra of the following compounds:
Dr. Manashi Chatterjee Week-2-Recitation
Chem-224

Explain clearly how one could use some spectroscopic technique to distinguish between
A and B. Indicate clearly what one would see in the spectra of both the compounds.
Dr. Manashi Chatterjee Week-2-Recitation
Chem-224

Match the compounds with the spectra below and explain the splitting patterns.
Dr. Manashi Chatterjee Week-2-Recitation
Chem-224
Dr. Manashi Chatterjee Week-2-Recitation
Chem-224
Dr. Manashi Chatterjee Week-2-Recitation
Chem-224

Compound X with Molecular Weight 164.2 shows the following peaks in the mass
spectrum: m/z 165 (2.4 %), 164 (21.5 %), 119 (base peak), 91 (34 %).
1
H NMR and IR spectrum are given below. Propose a reasonable structure for compound
X.
Show your work and explain the peaks in all 3 spectrums.
1
H NMR:
3H

3H

2H

2H 2H

IR Spectrum:

(Provide answer on next page)

Dr. Manashi Chatterjee Week-2-Recitation
Chem-224

Inf ormation f rom Mass

Inf ormation f rom IR

Inf ormation f rom NMR

Structure
Molecular f ormula
Dr. Manashi Chatterjee Week-2-Recitation
Chem-224

Some spectroscopic data for unknown compound (B) with molecular weight 202 and
molecular formula C10H18O4 are shown below. Use these data to answer the questions on
the next page.
Mass Spectrum: The base peak (100 % intensity) is at m/z = 160.

Dr. Manashi Chatterjee Week-2-Recitation
Chem-224
Dr. Manashi Chatterjee Week-2-Recitation
Chem-224
Dr. Manashi Chatterjee Week-2-Recitation
Chem-224
Dr. Manashi Chatterjee Week-2-Recitation
Chem-224
Dr. Manashi Chatterjee Week-2-Recitation
Chem-224
Dr. Manashi Chatterjee Week-2-Recitation
Chem-224

Give the number of expected signals (ignore splitting) in 1H spectra of the following
compounds:
Dr. Manashi Chatterjee Week-2-Recitation
Chem-224

Some spectroscopic data for unknown compound (A) with molecular weight 133.2 are
shown below. Use these data to answer the questions on the next page.

IR Spectrum:

Mass Spectrum: The base peak (100 % intensity) is at m/z = 54. The peaks at 133, 134,
135 and 136 have the following relative intensity (49:2:49:2) respectively.

1
H NMR and 13C NMR

13C - NMR Spectrum (proton decoupled)

1
H- NMR Spectrum

= 3.0 (triplet, integration = 1) ppm = 22, 25, 117 ppm

= 3.5 (triplet, integration = 1) ppm
Dr. Manashi Chatterjee Week-2-Recitation
Chem-224

a. What is the molecular formula of compound A? (3 points molecular formula and 5

points for reasoning using information from different spectra)

Molecular f ormula of A

b. What is the structure of compound A?