Organic Chemistry 2 Midterm Exam Prep Part 1 of 4 | Practice Questions & Video Solutions

Organic Chemistry 2 Midterm - Part 1 of 4

Problem 1
Problem 2
Problem 3
Problem 4
Problem 5
Problem 6
Problem 7
Problem 8
Problem 9
Problem 10
Problem 11
Problem 12
Problem 13
Problem 14
Problem 15
Problem 16
Problem 17
Problem 18
Problem 19
Problem 20
Problem 21
Problem 22
Problem 23
Problem 24
Problem 25
Problem 26
Problem 27
Problem 28

Organic Chemistry 2 Midterm - Part 1 of 4

Welcome to the Organic Chemistry 2 Midterm - Part 1 of 4 practice set!

SAMPLE

Please be aware that you practice a sample exam set, which means that it’s mimicking a real exam. In order to have more accurate experience:

Download the worksheet to save time writing
Start solving the practice problems
If you're stuck, watch the video solutions
See your summary to get more insights

Organic Chemistry 2 Midterm - Part 1 of 4

28 problems

1PRACTICE PROBLEM

Which bond is expected to vibrate at a higher wavenumber, C=N or C≡N?

views

rank

2PRACTICE PROBLEM

Identify the functional group(s) (conjugated ketone, ester, amide, nitrile, and alkyne) present in each unknown compound whose major IR peaks are listed below.

Compound A: 3165 cm^–1, 3000 cm^–1, and 1660 cm^-1
Compound B: 3050 cm^–1 (small peak), 1680 cm^–1 (strong peak)
Compound C: 1740 cm^-1 ,and 1260 cm^-1

views

3PRACTICE PROBLEM

Consider the following set of compounds.

Four chemical structures labeled (i) to (iv) for IR spectrum analysis.

Which of them is responsible for the IR spectrum given below?

IR spectrum graph showing transmittance versus wavenumber, used to analyze compound characteristics.

views

4PRACTICE PROBLEM

Determine if each of the following statements is true or false:

i. The coupling constant in hertz (Hz) is directly proportional to the operating frequency.

ii. Compared to the operating frequency in IR and UV-vis spectroscopy, the operating frequency in NMR spectroscopy is much higher.

views

5PRACTICE PROBLEM

How many signals appear in the ¹H NMR spectrum of the compound below?

Chemical structure of a compound for 1H NMR analysis in organic chemistry.

views

6PRACTICE PROBLEM

What is the relationship between the two products obtained when we replace H _a and H_b of propane-2-thione with deuterium? How many signals would you expect for these hydrogens in the ¹H NMR spectrum?

Chemical structure of propane-2-thione showing H_a and H_b positions for deuterium replacement.

views

7PRACTICE PROBLEM

A reaction produced a mixture of the following two compounds, which were separated. How can we determine which diastereomer is in which separated sample using only the ¹H NMR data?

views

8PRACTICE PROBLEM

How many different NMR signals will be observed in the NMR spectrum of each of the following compounds theoretically? Determine the approximate chemical shift for each proton and highlight any diastereotopic relationships.
(i) PhCHClCH₂Cl
(ii) vinyl bromide

views

9PRACTICE PROBLEM

Explain why the cis and trans isomers of the given alkene show no coupling between the a and c, as well as between the b and c protons.

Structural formulas of cis and trans isomers of 3-bromopent-2-enoic acid, highlighting proton positions.

views

10PRACTICE PROBLEM

For the hydrogen indicated in red, draw the expected ¹H NMR signal showing its estimated chemical shift.

Chemical structure with a red hydrogen atom indicating the focus for 1H NMR analysis.

views

11PRACTICE PROBLEM

Draw the expected signal for Ha in the below-given molecule with the help of given values.

Molecule structure showing Ha with chemical shifts and coupling constants.

views

12PRACTICE PROBLEM

Sketch the signal for a septet and determine the ratio of its peaks.

views

13PRACTICE PROBLEM

Give the predicted number of signals and the relative ratio of signal integrations for the molecule depicted below.

Chemical structure of tert-butylbenzene for NMR signal analysis.

views

14PRACTICE PROBLEM

An unknown compound with a molecular formula C₄H₆O₂ shows the following NMR spectrum. Propose a structure consistent with the observed absorptions.
NMR spectrum of an unknown compound C4H6O2 with labeled peaks.

comments

15PRACTICE PROBLEM

Draw the possible ¹³C NMR spectrum for the following compound.

Chemical structure of a compound with a bromine atom and an oxygen atom.

16PRACTICE PROBLEM

How can the following compounds be distinguished using only the techniques listed below and no other information?
a. using proton NMR spectroscopy
b. using ¹³C NMR with DEPT experiments.
c. using Infrared spectroscopy
Three chemical structures labeled I, II, and III for NMR and IR analysis in organic chemistry.

17PRACTICE PROBLEM

Determine the possible number/s of N in a neutral compound that contains C, H, and N with M⁺ = 84.

18PRACTICE PROBLEM

In the following mass spectrum, identify the peaks that represent the α-cleavage of heptan-3-one.

Mass spectrum showing peaks for heptan-3-one with labels a, b, c, d, and e for identification.

19PRACTICE PROBLEM

The mass spectrum of a compound shows peaks at m/z = 27 (71%), 29 (100%), 108 (94.7%), and 110 (91.5%). Provide the name of the compound.

20PRACTICE PROBLEM

a. Draw the structure of ethylbenzene, including all of the carbon and hydrogen atoms, as well as its resonance structures.

b. The ring of ethylbenzene is planar; demonstrate how the p and sp2 orbitals of carbon atoms form the ring, with orbitals overlapping above and below the plane.

views

21PRACTICE PROBLEM

Are the following structures aromatic? Explain.

views

22PRACTICE PROBLEM

Porphyrin is a group of compounds, one of which forms the core of heme molecules in hemoglobin. In the figure below, a large-ring iron complex is found at the center of the porphyrin. Encircle all the double bonds in the large cyclic conjugated pi system that contribute to its aromaticity. Determine the number of pi electrons present in this aromatic system.

<IMAGE>

views

23PRACTICE PROBLEM

Specify whether the ion below is aromatic, nonaromatic, or antiaromatic. If the ion is aromatic/antiaromatic, determine the value of n in Hückel's/Breslow's rule. If the ion is nonaromatic, explain your answer using the rules of aromaticity.

Chemical structure of an aromatic ion relevant to aromaticity in organic chemistry.

views

rank

24PRACTICE PROBLEM

Build a model that corresponds to the tub conformation of the following cyclooctatetraene derivative. Based on the model that you built, draw the tub conformation, and determine the magnitude of angle formed by p orbitals of adjacent pi bonds.
Structure of cyclooctatetraene derivative for tub conformation model.

views

rank

25PRACTICE PROBLEM

The following compound seems like an unlikely candidate for exhibiting optical activity as all its atoms are sp² hybridized and should theoretically lie flat. However, the compound does display chirality and has been found to have an extremely high optical activity. Explain why the compound is optically active and has a high degree of specific rotation.