Birla Institute of Technology & Science, Pilani - Hyderabad Campus
Second Semester 2022-23 CHEM F111 General Chemistry
Tutorial Test-3, Max. Marks: 20, Time: 45 min (8.05 AM to 8.50 AM)
Open Book Date: 22.06.2023
Model Solutions
1. The chemical shift of OH proton in ethanol is observed at 4.2 in a 60 MHz NMR instrument. If you
measure the same sample in an advanced instrument with 7.05 T field strength, calculate the precessional
frequency of this proton, and report the value only in Hz. (Given: γH = 26.752 x 107 T-1s-1). [3M]
Solution
ν = γBo/2 = (26.752 x 107 T-1s-1)(7.05)/2 = 300 MHz instrument
-TMS = [(4.2)(300 X 106 Hz)] / 106 = 1260 Hz
Actual precessional frequency = 1260 Hz + 300 MHz = 300001260 Hz
2. An aromatic compound with molecular formula C8 N2H4 shows the following spectral data:
1
H NMR (δ, ppm): only two singlets of equal integral ratios at 3.05 and 8.6.
IR (ν, cm-1): 3300, 3098, 2120, 1630, 1580.
Calculate IHD/DBE. Deduce the structure and mark the protons with the corresponding δ values and also
assign the IR functional groups. [4M]
Solution
DBE: 8
IR (cm-1): 3300 (sp C-H), 3098 (sp2 C-H), 2120 (C≡C), 1630 (C=C)
1
H NMR (ppm): 8.6 (aromatic H), 3.05 (alkyne H)
N
H H
3. Assign configuration at each stereocentre given (including the double bond) in the molecules A & B and
determine the stereochemical relationship between them. [3M]
Solution
As A & B are not superposable and not mirror images of each other, they are diastereomers.
4. Identify the major product in the following reaction and show the detailed steps leading to the product
formation [3M]
Solution:
5. Write the major product with (most stable conformation, wherever relevant) and the correct
stereochemistry, as applicable, in box provided next to the question. [1.5 + 1.5 = 3M]
6. Draw the most stable and unstable conformations of 2-methylbutane considering C2-C3 sigma bond rotation
in Newman projection. Calculate the individual energy and energy difference between those two
conformations if H↔H, H↔CH3, and CH3↔ CH3 eclipsed interaction energies are 4, 6, and 11 kJ/mol,
respectively, and CH3↔ CH3 gauche interaction energy is 3.8 kJ/mol. [4 M]
Solution
END