Answer:
The possible structures are ketone and aldehyde.
Explanation:
Number of double bonds of the given compound is calculated using the below formula.
[tex]N_{db}=N_{c}+1-\frac{N_{H}+N_{Br}-N_{N}}{2}[/tex]
[tex]N_{db}[/tex]=Number of double bonds
[tex]N_{c}[/tex] = Number of carbon atoms
[tex]N_{H}[/tex] = Number of hydrogen atoms
[tex]N_{N}[/tex] = Number of nitrogen atoms
The number of double bonds in the given formula - [tex]C_{4}H_{8}O[/tex]
[tex]N_{db}= 4+1-\frac{8+0-0}{2}=1[/tex]
The number of double bonds in the compound is one.
Therefore, probable structures is as follows.
(In attachment)
The structures I and III are ruled out from the probable structures because the signal in 13C-NMR appears at greater than 160 ppm.
alkene compounds I and II shows signal less than 140 ppm.
Hence, the probable structures III and IV are given as follows.
The carbonyl of structure I appear at 202 and ketone group of IV appears at 208 in 13C, which are greater than 160.
Hence, the molecular formula of the compound [tex]C_{4}H_{8}O[/tex] having possible structure in which the signal appears at greater than 160 ppm are shown aw follows.
