Mass spectrometry of an unknown compound revealed a...

Mass spectrometry of an unknown compound revealed a molecular ion at m/z 158. The IR spectrum, the $^{13}C$ DEPT spectrum, and the $^1H$ NMR spectrum are shown below. Draw the structure of this compound.

Transcript

00:01 Hello everyone and this question on the basis of the ir spectrum we have to identify the function group and on the basis of the nmr we have to depict the structure of the molecule.

00:09 So first let's see for the ir spectrum.

00:15 For the ir spectrum the values that are given first it is 3320 centimeter inverse and the other value that is given as 1690 centimeter inverse.

00:29 So for 3320 inverse we can say that either it can have the oh group the oh functional group that is called the alcohol functional group or the nh group that is that is basically our amine functional group.

00:47 So these are the two functional groups which are possible for the range of 3320 centimeter inverse.

00:53 The other is given as 1690 centimeter inverse.

00:56 So it is basically for the membered carbonyl compound or we can say that it is for the the value ranges in the range of 1715 for the carbonyl compound but when it is for the less membered ring then a value decreases or when there is a conjugation the value decreases so the value comes in this region.

01:18 So it is for carbonyl compound carbonyl compound so this carbonyl can be either aldehyde sorry either ketone or aldehyde.

01:27 Basically it is for ketone itself we take it for ketone but we can say it is for carbonyl compound.

01:34 The value is basically in the range of if i describe the value it is basically in the range of 1715 centimeter inverse but due to conjugation due to conjugation the value decreases the value decreases hence it comes in this region...

Question

Mass spectrometry of an unknown compound revealed a molecular ion at m/z 158. The IR spectrum, the $^{13}C$ DEPT spectrum, and the $^1H$ NMR spectrum are shown below. Draw the structure of this compound.

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