Phospholipids are a class of compounds largely responsible for the bilayer structure of
Chapter 15, Problem 15.79(choose chapter or problem)
Phospholipids are a class of compounds largely responsible for the bilayer structure of cell membranes of plants and animals (discussed in Chapter 26). The phospholipid shown below has two unbranched hydrocarbon chains, one of which contains an alkene group with a cis configuration. A mass spectrum of this phospholipid in negative ion mode (where anions are detected instead of cations) shows a peak for the molecular ion at m/z = 673. When ozone is present, a new peak appears at m/z = 563 (J. Am. Chem. Soc. 2006, 128, 5859). O O O O C17H33 C15H31 O P O O HO @ (a) Draw the full structure of the phospholipid (indicating the position of the alkene group) consistent with these data. (b) When methanol is used as a solvent in the experiment with ozone present, the appearance of the peak at m/z 563 is accompanied by a peak at m/z = 611. When the solvent is changed to ethanol, the peak at m/z = 563 remains, but the peak at m/z = 611 is shifted to 625. Propose an explanation consistent with these findings.
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