Questions For Assignment 1 CHM557

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SEMESTER 20214 ASSIGNMENT 1 CHM556/CHM557

ASSIGNMENT 1 – SPECTROSCOPY (40 MARKS)

QUESTION 1

The IR spectrum below belongs to an organic compound A having one nitrogen atom.
Determine which structures that fits to the IR spectrum. Justify your answer by providing two (2)
IR absorption peaks with their wavenumber.

CN NH2 N

(4 marks)
SEMESTER 20214 ASSIGNMENT 1 CHM556/CHM557

QUESTION 2

An unknown compound B is a saturated compound having a molecular formula of C 3H8O.


Oxidation of compound B with PCC afforded compound C that gives positive result in Tollens’
test. Based on the IR spectrum below, determine structure of compound B and justify your
answer.

(4 marks)
SEMESTER 20214 ASSIGNMENT 1 CHM556/CHM557

QUESTION 3

Briefly explain how you might distinguish between the following substances by comparing their
1
H NMR spectra.

a.
O
O
O
and O

Compound I Compound II

(2 marks)

b. Propanal and acetone


(5 marks)
SEMESTER 20214 ASSIGNMENT 1 CHM556/CHM557

QUESTION 4

Following are the 1H NMR spectra of three isomeric esters, X, Y and Z with the molecular formula
C6H12O2.

a. Provide structure for each ester and assign peaks to show which protons give rise to
which signals in the spectrum.
(11 marks)

b. Identify number of signals that would be appeared in the 13C NMR spectrum of each
isomer.

(3 marks)
SEMESTER 20214 ASSIGNMENT 1 CHM556/CHM557
SEMESTER 20214 ASSIGNMENT 1 CHM556/CHM557

QUESTION 5

The IR, 1H NMR and 13C NMR spectra of compound P are shown below. The molecular formula
for compound P is C5H7NO2.

a. Identify three (3) important absorption peaks on the IR spectrum and indicate the bond
and wavenumber associated with each peak.

b.
Elucidate the structure of compound P and assign each peak in the 1H and 13C NMR spectra.
(Hint: The compound consists of more than one functional group).
SEMESTER 20214 ASSIGNMENT 1 CHM556/CHM557
SEMESTER 20214 ASSIGNMENT 1 CHM556/CHM557

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