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Question: purified product as well as the indene starting material your...

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purified product as well as the indene starting material. Your TA will give you a C NMR spectrum of your product. Hand this in with your postlab report Post Lab Questions (1) Write the mechanism for the two steps of the hydroboration/oxidation reaction of indene. (2) Compare the IR spectra of your purified product and the indene starting material. They will be rather similar, with one big difference. Describe the nature (frequency, broadness, strength) of the new peak in the product spectrum, and explain what functional group this new peak denotes. (3) IR can tell the presence or absence of functional groups in a molecule. Can it distinguish between the two potential products of this reaction? Explain your answer. OH or (4) A key concept in 3C NMR spectroscopy is symmetry- if two carbon atoms are related by symmetry only one peak is seen for them in the spectrum. With that in mind, how many peaks would you expect to see in the C NMR spectra of the following molecules? Page | 10 Chem 08B Lab Manual Winter 2019 NH2 CI (5) You were provided with a C NMR spectrum of your product. How many peaks are present in the aromatic region of the C spectrum? How many peaks are present in the aliphatic/sp region of the spectrum? (6) Based on your answers to Q4/5, determine the structure of your product. Which isomer was formed? Explain your answer with respect to the NMR data. (7) Go back to the mechanism of reaction you wrote in Q1. Explain the observed regioselectivity of the reaction, i.e. in chemical terms, why do you get the isomer from Q6?
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