Tutorial (In-class Exercise)

1. Below is the IR spectrum and NMR spectrum of compound A. Compound A having a

molecular formula of C5H10O.

IR Spectrum
 (a) Fill the table below based on NMR spectrum.
(10 marks)

Chemical Shift, ppm _________ 1.60 2.10 2.40

Splitting pattern _________ _________ ________ ________

Integration 3 2 ____________ 2

Number of H on the
neighboring Carbon.
____________ ____________ ___________ ____________

(b) Deduce the structure of compound A based on the table a and IR spectrum.
(2 marks)
2. A lab assistant has found an unidentified bottle of chemical. He labelled the sample
as A and performed spectroscopic analysis (NMR) to identify the sample.

a. Below is the proton NMR spectrum for sample A and the molecular formula for
sample A is C4H8O. Complete the table below by referring to the spectrum and draw
the molecular structure of compound A.

Chemical shift/ ppm Splitting pattern Number of coupled (adjacent) H

1.05

2.12

2.45

Molecular Structure of A:
b. Predict and draw the proton NMR spectrum for the molecule below. Your spectrum
should include the chemical shift, splitting pattern and integration of all the hydrogens
involved. (10M)