Chapter 12: Q25P (page 640)
Three IR spectra are shown, corresponding to three of the following compounds. For each spectrum, determine the structure and explain how the peaks in the spectrum correspond to the structure you have chosen.




Short Answer

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Chapter 12: Q25P (page 640)
Three IR spectra are shown, corresponding to three of the following compounds. For each spectrum, determine the structure and explain how the peaks in the spectrum correspond to the structure you have chosen.





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The mass spectrum of n-octane shows a prominent molecular ion peak (m/z 114). There is also a large peak at m/z 57, but it is not the base peak. The mass spectrum of 3,4-dimethylhexane shows a smaller molecular ion, and the peak at mass 57 is the base peak. Explain these trends in abundance of the molecular ions and the ions at mass 57 and predict the intensities of the peaks at masses 57 and 114 in the spectrum of 2,2,3,3-tetramethylbutane.
For each spectrum, interpret all the significant streching frequencies above 1580 cm-10


Predict the characteristic infrared absorptions of the functional groups in the following molecules.
(a) cyclopentene
(b) hexan-2-ol
(c) hexan-2-one
(d) hex-1-yne
(e) dimethylamine
(f) hexanoic acid
(g) hexanenitrile
(h) methyl acetate
(i) hexanamide.
Question: (Another true story.) A student who was checking into her lab desk found an unlabeled sample from a previous student. She was asked to identify the sample. She did an IR spectrum and declared, 鈥淚t looks like an alkane.鈥 But it seemed too reactive to be an alkane, so she did a GC鈥揗S. The mass spectrum is shown next. Identify the compound as far as you can, and state what part of your identification is uncertain. Propose fragments corresponding to the numbered peaks.

Question: Consider the following four structures, followed by mass spectral data. Match each structure with its characteristic molecular ion or fragment. In each case, give a likely structure of the ion responsible for the base peak

(a) base peak at 105
(b) base peak at 72
(c) doublet at 198 and 200, base peak at 91
(d) base peak at 91, large peak at 43
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