Question

Investigate the following IR Absorption, ¹³C and ¹H NMR below:

Compound X's IR (BELOW)

0 8 7 0 5 48 22 76 97 98 50 37 11 10 34 530 0934279953113533730 67 34 11 30 9 6 748481 8-305247803 0 8 Wavenumber cm-1

Compound X's ¹³C NMR (BELOW)

Compound X's ¹H NMR (BELOW)

1. Investigate the diagnostic IR Absorption of compound X shown above and use this to determine the functional groups present. Use a table that goes (as an example):

(EXAMPLE ONLY)

Frequency (cm-1)	Relative Intensity or Shape	Vibrational Assignment
2950	Medium	C-H Stretch
1715	Sharp and Strong	C double bond O Stretch

2. Investigate the ¹H and ¹³C NMR data of compound X shown above and use this to determine the carbon-hydrogen framework of the molecule. Use a table that goes (as an example):

(EXAMPLE ONLY)

Carbon Number	Observed, $\delta$ (parts per million)	Assignment	Expected Chemical Shift, $\delta$ (parts per million)
C1	40	CH2-O	40-50

(EXAMPLE ONLY)

Hydrogen Number	Integral	Signal Multiplicity	Exptl. $\delta$ (parts per million)	Assignment	Expected Chemical Shift, $\delta$ (parts per million)
H1		Triplet	1.32	CH3C-O-	1.2

Present the most likely structure based on the IR Absorption, ¹H and ¹³C NMR data to support your case. If there is more than one compound that fits the data provided, present all the structure of the compound.

Answer 1