Ethers are not easily differentiated by their infrared spectra, but they tend to form predictable fragments in the mass spectrum. The following compounds give similar but distinctive mass spectra.

Both compounds give prominent peaks at m/z 116, 73, 57, and 43. But one compound gives a distinctive strong peak at 87, and the other compound gives a strong peak at 101. Determine which compound gives the peak at 87 and which one gives the peak at 101. Propose fragmentations to account for the ions at m/z 116, 101, 87, and 73?

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butyl propyl ether butyl isopropyl ether