Chapter 12: Q 42 E (page 385)
Question: The mass spectrum (a) and the infrared spectrum (b) of another unknown hydrocarbon are shown. Propose as many structures as you can.


Short Answer

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Chapter 12: Q 42 E (page 385)
Question: The mass spectrum (a) and the infrared spectrum (b) of another unknown hydrocarbon are shown. Propose as many structures as you can.



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At what approximate positions might the following compounds showIR absorptions?
(d)

Aprobarbital, a barbiturate once used in treating insomnia, is synthesized in three steps from diethyl malonate. Show how you would synthesize the necessary dialkylated intermediate, and then propose a mechanism for the reaction of this intermediate with urea to give aprobarbital.

Question: Why do you suppose accidental overlap of signals is much more common in1H NMR than in13C NMR?
Predict the product and provide the complete electron-pushing mechanism for the following two-step synthetic processes:

Fill in the multiple bonds in the following model of naphthalene, (gray 5 C, ivory 5 H). How many resonance structures does naphthalene have? Draw them.

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