Draw a structure for an alcohol that exhibits a molecular ion at M+ = 88 and that produces fragments at m/z = 73, m/z = 70 and m/z = 59.

3-pentanol

Explanation:

In this case, we have alcohol as the main functional group (OH) with a molecular ion at 88. If the molecular ion is 88 the molar mass is also 88 g/mol therefore the formula for the unknown molecule is .

Additionally, if the mass spectrum shows the molecular ion peak we can not have tertiary alcohols (tertiary alcohols often do not show M+ at  all). So, the structures only can be primary and secondary structures.

With this in mind, our options are:

-) 1-pentanol

-) 2-pentanol

-) 3-pentanol

Now we can analyze each structure:

-) 1-pentanol

The structure must explain all the fragments produced (73, 70, and 59). In this primary alcohol, we will have an alpha cleavage (the red bond would be broken). If this has to happen, we will have fragments at 31 and 57. These fragments dont fit with the reported ones, therefore this is not a possible structure (See figure 1).

-) 2-pentanol

On this structure, we will have also an alpha cleavage (red bond). In this rupture we will have fragments at 45 and 43, these m/z values dont fit with the reported ones, therefore this is not a possible structure (See figure 1).

-) 3-pentanol

In this structure, we have the "OH"  bonded to carbon three. So, we can analyze each fragment:

   -) m/z 59

This fragment, can be explained as an alpha cleavage. But, in this case we have two ruptures that can produce the same ion. The carbons on both sides of the C-OH bond.

   -) m/z 71

This fragment, can be explained as a loss of water (M-18) in which we have the production of a carbocation in the carbon where we previously have the C-OH bond.

   -) m/z 73

This fragment, can be explained as a beta cleavage. But, in this case, also we have two ruptures that can produce the same ion. The methyl groups on each end molecule.

See figure 2

I hope it helps!