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An acid-catalyzed reaction was carried out using methyl
Chapter 24, Problem 46SP(choose chapter or problem)
An acid-catalyzed reaction was carried out using methyl cellosolve (2-methoxyethanol) as the solvent. When the 2-methoxyethanol was redistilled, a higher-boiling fraction (bp \(162\ ^{\circ} \mathrm{C}\)) was also recovered. The mass spectrum of this fraction showed the molecular weight to be 134 . The IR and NMR spectra are shown here. Determine the structure of this compound, and propose a mechanism for its formation.
Equation Transcription:
Text Transcription:
162 ^{o}C
NMR
(m)
(cm^{-1})
CDCl_3
0Hz
50Hz
3.7{delta}
3.6{delta}
3.5{delta}
delta(ppm)
Questions & Answers
QUESTION:
An acid-catalyzed reaction was carried out using methyl cellosolve (2-methoxyethanol) as the solvent. When the 2-methoxyethanol was redistilled, a higher-boiling fraction (bp \(162\ ^{\circ} \mathrm{C}\)) was also recovered. The mass spectrum of this fraction showed the molecular weight to be 134 . The IR and NMR spectra are shown here. Determine the structure of this compound, and propose a mechanism for its formation.
Equation Transcription:
Text Transcription:
162 ^{o}C
NMR
(m)
(cm^{-1})
CDCl_3
0Hz
50Hz
3.7{delta}
3.6{delta}
3.5{delta}
delta(ppm)
ANSWER:
Solution 46SP
From the given data:
IR (cm-1) 1200, 1450, 2800 - 300
NMR: 35(triplet) 3.7
(triplet), 3.48
(singlet)
m/z:134 (M+)