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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Draw the structure of an alkene that yields only acetone, , on ozonolysis followed by treatment with Zn.
4-Methyl-2-pentanone and 3-methylpentanal are isomers. Explain how
you could tell them apart, both by mass spectrometry and by infrared
spectroscopy.

Two mass spectra are shown in Figure 12-8. One spectrum is that of 2-methyl-2-pentene; the other is of 2-hexene. Which is which? Explain.
a.

b.

Question: How could you use infrared spectroscopy to distinguish between the
following pairs of isomers?
(a)
(b)
Reaction of acetone with yields hexadeuterioacetone. That is, all the hydrogens in acetone are exchanged for deuterium. Review the mechanism of mercuric-ion-catalyzed alkyne hydration, and then propose a mechanism for this deuterium incorporation.

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