AS/CHM556/JUN 12

ASSIGNMENT 4
(Spectroscopy)

1.

The molecular formula of an acyl compound, Y is given as C10H12O2. Given below are
the 1H NMR spectral date and carbonyl absorption peaks of Y. Propose a structure
for Y. Please justify your answer.
1

H NMR spectrum

IR spectrum

Triplet

1.2 (3H)

Singlet

3.5 (2H)

Quartet

4.1 (2H)

Multiplet

7.3 (5H)

1740 cm-1

(5 marks)
2.
O
CH3CH2CH2CCH3
Compound A

O
CH3CH2CH2CH
Compound B

Compounds A and B are isomeric carbonyl compounds. Both show an IR absorption

at around 1700 cm-1 for the CO group. However, the 1H NMR spectra for the two
compounds look different. Sketch the expected 1H NMR spectrum for compounds A
and B showing the splitting patterns, approximate chemical shifts, and integration
ratio of the signals.
(5 marks)