The infrared spectrum of the compound with the mass spectrum shown below lacks a
ID: 985318 • Letter: T
Question
The infrared spectrum of the compound with the mass spectrum shown below lacks any significant absorption above 3000 cm-1. There is a distinct peak near 1740 cm-1 and another strong peak near 1200 cm-1.
molecular ion: M+ = 172.
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Which of the following structures is consistent with the data?
100 80 70 20- 4 10 20 30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 Reprinted courtesy of the National Institute of Standards and Technolog copprightable in rhe United States Us. Deparmert of Commence. NotExplanation / Answer
Option C is the correct answer.
The infrared spectrum of the compound with the mass spectrum shown lacks any significant absorption above 3000 cm-1. Hence, alcohol or carboxylic acid functional groups are absent. Thus, options A and D are ruled out.
There is a distinct peak near 1740 cm-1 and another strong peak near 1200 cm-1. This indicates the presence of ester functional group.
In the mass spectrum, the strong peak at m/z 88 confirms that alpha carbon atom is unbranched. Hence, option C is the correct answer.
Note: The peak at m/z is due to McLafferty rearrangement.
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