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Assignment 1-Spectroscopy - Oct2020-Feb2021

This document contains an assignment for an organic chemistry class involving spectroscopy. The assignment contains 6 questions analyzing infrared spectroscopy (IR) and nuclear magnetic resonance (NMR) data to determine structures of unknown compounds. Several of the questions involve proposing structures for isomers based on their spectroscopic data and reactions. The last question discusses a discrepancy between IR spectra for an unknown compound taken initially and after several days, and asks students to explain the reason for the change and how to prevent such issues.

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Amirah Azlan
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227 views

Assignment 1-Spectroscopy - Oct2020-Feb2021

This document contains an assignment for an organic chemistry class involving spectroscopy. The assignment contains 6 questions analyzing infrared spectroscopy (IR) and nuclear magnetic resonance (NMR) data to determine structures of unknown compounds. Several of the questions involve proposing structures for isomers based on their spectroscopic data and reactions. The last question discusses a discrepancy between IR spectra for an unknown compound taken initially and after several days, and asks students to explain the reason for the change and how to prevent such issues.

Uploaded by

Amirah Azlan
Copyright
© © All Rights Reserved
Available Formats
Download as PDF, TXT or read online on Scribd
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SEMESTER 20204 ASSIGNMENT 1 CHM557

ORGANIC CHEMISTRY

ASSIGNMENT 1

SPECTROSCOPY
Semester October 2020-February 2021
Online Assessment COVID19

Name :

Student ID :

Group :
SEMESTER 20204 ASSIGNMENT 1 CHM557
ORGANIC CHEMISTRY

QUESTION 1

An unknown compound with a molecular formula of C6H10O2 gives the IR and NMR spectra
shown below.

a) Identify the functional groups in the IR spectrum, and explain your answer.

b) A very deshielded signal is observed at 172 ppm in the carbon NMR spectrum.
How does this signal correlate with absorption in the IR spectrum.

c) Determine the degree of unsaturation for the compound.

d) Suggest a structure for this compound (students are not required to explain the splitting pattern
from the proton NMR spectrum).
SEMESTER 20204 ASSIGNMENT 1 CHM557
ORGANIC CHEMISTRY

QUESTION 2

The following spectra for A and B correspond to two structural isomers with a molecular formula of
C4H11N. The NMR singlet at δ1.16 in spectrum A disappears when the sample is shaken with D2O. The
singlet at δ0.60 ppm in the spectrum of B disappears on shaking with D2O. Propose structures for these
isomers, and explain how it is consistent with the observed absorptions.
SEMESTER 20204 ASSIGNMENT 1 CHM557
ORGANIC CHEMISTRY
SEMESTER 20204 ASSIGNMENT 1 CHM557
ORGANIC CHEMISTRY

QUESTION 3

Compounds Y and Z are isomers with the molecular formula C10H12O. The IR spectrum of each
compound shows a strong absorption band near 1710 cm−1. The 1H NMR spectra of Y and Z are
given below. Propose structures for Y and Z.
SEMESTER 20204 ASSIGNMENT 1 CHM557
ORGANIC CHEMISTRY

QUESTION 4

Compound A (C9H18O) forms a phenylhydrazone, but it gives a negative Tollens’ test. The IR
spectrum of A has a strong band near 1710 cm−1. The broadband carbon NMR spectrum of A is given
below.

a) Propose a structure for A and explain how your structure fits the spectral data.

b) Propose a mechanism for this reaction.

QUESTION 5

Compounds W and X are isomers. They have the molecular formula C9H8O. The IR spectrum of
each compound shows a strong absorption band near 1715 cm−1. Oxidation of either compound with
hot, basic potassium permanganate followed by acidification yields phthalic acid. The proton NMR
spectrum of W shows a multiplet at δ 7.3 and a singlet at δ 3.4. The proton NMR spectrum of X
shows a multiplet at δ 7.5, a triplet at δ 3.1, and a triplet at δ 2.5. Propose structures for W and X.
SEMESTER 20204 ASSIGNMENT 1 CHM557
ORGANIC CHEMISTRY

QUESTION 6

The manager of an organic chemistry stockroom prepared unknowns for a ‘Ketone and Aldehyde’
experiment by placing two drops of the liquid unknowns in test tubes labelled A and B. He then
stored the test tubes for several days until they were needed. On the day of the experiment, the
students complained the IR spectrum measured for test tube A is different from the spectrum shown
by the stockroom manager at the end of the class (refer the picture below). Obviously something has
happen to the solution while being left for a few days.
Test tube A - manager Test tube A - students

1725 cm-1 1710 cm-1

a) Identify the functional group revealed by the IR spectrum of


i. The stockroom manager
ii. The students

b) Explain the reason of discrepancy between the stockroom manager’s spectrum and the
student’s results.

c) Suggest how this misunderstanding might be prevented.

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