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    Spectrums and Reactions

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    1. i. Clearly draw the structure of the Lopinavir. (You can find the structure using any internet
    search engine.)

    ii. What is the use of Lopinavir? (maximum: two sentences)

    iii. On the structure that you have drawn label the following groups, if present: one phenyl ring,
    one benzyl ring, one amide, one aldehyde, one ketone, one ester, one alkyne, one alkene,
    one 1o alcohol, one 2o alcohol, one 3o alcohol, one 1o amine, one 2o amine, one 3o amine and
    one ether.

    2. The mass spectrum below corresponds to C7H7X:  benzyliodide, benzylbromide, benzylchloride or benzylfluoride.

    i. Calculate the degree of unsaturation for these compounds.

    ii. Based on your analysis of the mass spectrum, what is the molecular formula and structure
    of the compound? Give the reason for your answer using data from the spectrum below.  In
    addition, in your answer state why you were able to determine that the other halogens
    were not present. You are not required to analyze the peaks below m/z 75. (maximum: 4

    iii. What is the m/z‐value of the base peak?  

    iv. How is the ion for the base peak formed? In your answer, show the mechanism for formation of this ion.

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    Solution Preview

    Please find the complete solutions attached.

    1. Reference: http://www.mcld.co.uk/hiv/?q=lopinavir
    Lopinavir is an antiretroviral developed by Abbott to treat HIV/AIDS and is administered as a coformulation with an earlier Abbott drug, Ritanovir (this helps bioavailablity).

    i. Degree of Unsaturation = [2 + (2 x #Carbons) + #Nitrogens - #Hydrogens - #Halogens]/2
    = [2 + (2 x 7) + 0 - 7 - 1]/2
    = 4
    benzyl chloride
    The dominant molecular ion corresponds to 126 m/z which is the calculated molecular mass for this compound. The other major signal at 91 m/z ...

    Solution Summary

    The solution examines spectrum and reactions for chemical structures.