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Assignment CHM557

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8 views

Assignment CHM557

Uploaded by

aizati
Copyright
© © All Rights Reserved
Available Formats
Download as PDF, TXT or read online on Scribd
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ASSIGNMENT CHM557

OCT2022 – FEB2023

1. The following is the IR spectrum of alcohol, which has the molecular formula C 2H6O.
Select three (3) significant peaks associate with the alcohol from the given spectrum.
State the wavenumber and the bond associated with each peak you selected.

(6 mark)

2. Isopropyl alcohol can be oxidized to acetone via hot oxidation of sodium dichromate
i) Sketch a predicted 1H NMR spectrum for isopropyl alcohol with signals in
estimated chemical shift ranges and with expected splitting.
(4 mark)

ii) Give the integral values as a whole number ratio for the signals in the 1H NMR
spectrum of isopropyl alcohol
(2 mark)

iii) How many 13C NMR signals would you predict for isopropyl alcohol?
(1 mark)

iv) State the oxidizing agent for the above reaction other than sodium dichromate
(1 mark)

3. Two aromatic compounds (A and B) have the same molecular formula of C9H10O.
They both show infrared spectra with a strong absorption at 1710 nm-1. Determine
the structure of the compounds if the show the following 1H NMR data.

Compound A Compound B
3.0 ppm, singlet, 3H 0.98 ppm, triplet, 3H
3.7 ppm, singlet, 2H 2.3 ppm, quartet, 2H
7.4 – 7.6 ppm, multiplet, 5H 7.4 – 7.6 ppm, multiplet, 5H

(6 mark)
4. Compound E with a molecular formula of C4H8O, gives a positive iodoform test and
has the following 1H NMR

Compound E
Triplet, 1.3 ppm
Singlet 2.1 ppm
Quartet, 2.7 ppm

i) Suggest the structure of E .


(2 mark)

ii) Outline an equation for the reaction between compound E and the Iodoform
Test.
(3 mark)

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