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Chapter 13: Q 39. (page 522)

Question:Primary (1°) alcohols often show a peak in their mass spectra at m/z= 31. Suggest a structure for this fragment.

Short Answer

Expert verified

Answer

Structure of the fragment that shows peak at m/z = 31

Step by step solution

01

α cleavage of alcohols

Alcohols undergo fragmentation to give a dehydrated radical cation and cations and neutral radicals uponα cleavage.

02

Step 2: α cleavage of primary alcohols

Primary alcohols can cleave to form an alkyl radical and a carbocation containing the alcohol group. This carbocation is resonance stabilized and has an m/z value of 31.

The cleavage of a primary alcohol is shown below:

αcleavageof primary alcohol

The cation formed is resonance stabilized; the canonical structure is shown below:

Resonance stabilization of the carbocation formed

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