Experiment 11

STUDENT ANSWERS

NAME: DATE:

STUDENT NUMBER:

EXPERIMENT 11: SEPARATION OF TWO SUBSTITUTED AROMATICS

BY COLUMN CHROMATOGRAPHY

QUESTIONS

1) Assign the data for the IR and 1H NMR spectra for compounds A and B by
filling in the Tables below.
a) IR

Compound Absorption (cm-1) Assignment

1675
A
3100

1690
B
3100

(4)

b) 1
H NMR

Chemical Multiplicity &

Compound Assignment
Shift () in ppm Integration

3.96

6.30

A 7.03

7.41

9.81

B 3.93

6.85

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Chemical Multiplicity &

Compound Assignment
Shift () in ppm Integration

6.97

7.43

7.81

10.76

(11)

2) Using the above spectroscopic and CHN data, propose structures for A and B.
Give their IUPAC names. Present rational interpretations of the data.
Hint data = A is found in vanilla essence while B is a key component of
the liniment muscle rub “deep heat”.
(10)
Interpretation of the data followed by the structures of A and B:

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3) Record the millimoles of both A and B and the recovery masses. Give the yield
of recovery for both A and B, and the melting point of A, i.e., fill in all the blank
spaces.
(5)
Rel. No. of %
mp
Molecular mass (g) millimole recovery
(pure)
Mass s yield
81 to 83 °C;
Compound A 152 0.25 g - bp = 285 °C

Your mp =
Compound A Recovered =
152
product

0.25 mL
Compound B 152 (d = 1.174) - bp = 222 °C
m = 0.293 g
Compound B
152 Recovered = -
product

4) Rationalise their relative Rf values based on the polarity trends mentioned

before.
(2)
Relative polarity order with explanation:

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5) Give an alternative method (see data in 3) above) in order to separate

compounds A and B.
(2)
Description of separation method:

6) A and B are constitutional isomers. Explain the meaning of this term using A
and B to illustrate your explanation. Propose a structure for a heteroaromatic
constitutional isomer of molecular formula C8H8O3.
(6)
Definition of “constitutional isomer”; A and B to illustrate the term:

Structure of a heteroaromatic with the formula C 8H8O:

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TOTAL = [40]