Analysis

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Question 8
Hard

Compound X is an organic compound containing carbon, hydrogen, and oxygen only. The 1 ^1\,1H NMR spectrum of compound X is shown below. The numbers in parentheses by the peaks are the relative peak areas.

The ^1\,H NMR spectrum of compound X.

Compound X is refluxed with aqueous hydrochloric acid, forming two organic compounds Y and Z.

  • The infrared spectrum of Y contains a very broad peak in the range 2500−3300 cm−12500-3300\text{ cm}^{-1}2500−3300 cm−1 and a sharp, strong peak at 1715 cm-1.
  • The infrared spectrum of Z contains a broad peak in the range 3200−3600 cm−13200-3600\text{ cm}^{-1}3200−3600 cm−1, but does not show any peaks in the range 1630−1820 cm−11630-1820\text{ cm}^{-1}1630−1820 cm−1.

Use the information provided to suggest a structure for compound X. Show all of your reasoning.

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Analysis Questions

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