Chapter 13: Q 27. (page 521)
Question: Propose two molecular formulas for each molecular ion: (a) 102; (b) 98; (c) 119; (d) 74.
Short Answer
Answer
a. molecular ion 102:,
b. molecular ion 98: ,
c. molecular ion 119:,
d. molecular ion 74: , ,
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Chapter 13: Q 27. (page 521)
Question: Propose two molecular formulas for each molecular ion: (a) 102; (b) 98; (c) 119; (d) 74.
Answer
a. molecular ion 102:,
b. molecular ion 98: ,
c. molecular ion 119:,
d. molecular ion 74: , ,
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Question: The carbonyl absorption of an amide typically occurs in the 1630–1680 cm-1 range, while the carbonyl absorption of an ester occurs at much higher wavenumber, typically 1735–1745 cm-1 . Account for this difference.
Question: Reaction of tert-butyl pentyl ether with HBr forms 1-bromopentane and compound B. B has a molecular ion in its mass spectrum at 56 and gives peaks in its IR spectrum at 3150–3000, 3000–2850, and 1650 cm-1. Propose a structure for B and draw a stepwise mechanism that accounts for its formation.
Question: What functional groups are responsible for the absorptions above 1500 in the IR spectra for compounds A and B?

Question:Reduction of cyclohex-2-enone can yield cyclohexanone, cyclohex-2-enol, or cyclohexanol, depending on the reagent and reaction conditions. How could you use IR spectroscopy to distinguish the three possible products?

Question:For each compound, assign likely structures to the fragments at each m/zvalue, and explain how each fragment is formed.
a. : peaks at m/z= 104, 91
b. : peaks at m/z= 71, 68, 41, 31
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