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9. Propose a structure for a molecule whose mass spectrum shows a parent ion at m/z 102 (M), IR peaks at 1740 and 1150 cm whi
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Answer #1
  • First, we count the Number. of Hydrogens. H=10
  • Then we see that the there is an IR peak at around 1740 cm-1. This suggests a C=O stretching. This means that the molecule may have a double bond. Further, the IR peak corresponding to 1150 cm-1 is for C-O. This suggests that an ester group might be present because there are both C=O and C-O bonds We will assume only one double bond.
  • We know that Hydrogen deficiency index, HDI = (2C+2-H)/2. Putting H=10 and assuming HDI =1 (Corresponding to C=O, we will have no. of carbon atoms as 5.
  • Thus the formula of an ester with 5 carbon becomes C5H10O2. Mass of this compound will be 102 g/mol. This corresponds to the m/z parent peak of 102. Thus, the chemical formula is confirmed. Now we will use NMR data to predict the compound.
  • We notice a  -CH3 group having a single peak at around 2.3 ppm. This means that this CH3 signal does not undergo splitting and thus it must be attached to the C=O i.e. the Carbonyl carbon.
  • 2H near 4.2 ppm suggests -CH2 group attached to Oxygen and because it is a triplet, it suggests that it is further attached to -CH2 group.
  • The second -CH2- group at 1.7 ppm is a sextet means that one one side it is attached by -CH2- and on other side we have -CH3 group having 0.9 ppm

о (0.9, ЗН, t) (4.2, 2H, t) СHз НзС (1.7, 2H, sextet) (2.3, зн, s) Propyl Acetate

  • Completing the structure, we have,
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