A flavor chemist attempted to isolate and identify the major flavor component of a recently discovered wild berry. A sample of berries was pureed in a blender , and the resulting slurry was dissolved in ethyl acetate. The solution was first extracted with 0.1 M HCI, followed by extractions with aqueous sodium bicarbonate. The ethyl acetate portion was concentrated and thin layer chromatography of the resulting oil indicated two compounds. Compound 1 with Rf of 0.2, and Compound 2 with an Rf of 0.6. The two compounds were separated by column chromatography, and the top spot (Compound 2) was identified as the essential oil. Compound 2 had the following physical characteristics: Formula: C11H1403 IR: 3100, 2950, 1735, 800 cm-1 1H NMR: 7.5 ppm, multiplet, 4H 4.5 ppm, septet, 1H 2.1 ppm, singlet, 3H 1.4 ppm, doublet, 6H According to the IR data given, which of the following functional groups is NOT present in Compound 2? O A. Alcohol O B. Carbon - carbon double bond O C. Ester O D. Carbon - carbon single bond

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A flavor chemist attempted to isolate and identify the major flavor component of a recently discovered wild berry. A
sample of berries was pureed in a blender , and the resulting slurry was dissolved in ethyl acetate. The solution was first
extracted with 0.1 M HCI, followed by extractions with aqueous sodium bicarbonate.
The ethyl acetate portion was concentrated and thin layer chromatography of the resulting oil indicated two compounds.
Compound 1 with Rf of 0.2, and Compound 2 with an Rf of 0.6. The two compounds were separated by column
chromatography, and the top spot (Compound 2) was identified as the essential oil. Compound 2 had the following
physical characteristics:
Formula: C11H1403
-1
IR: 3100, 2950, 1735, 800 cm"
1H NMR: 7.5 ppm, multiplet, 4H
4.5 ppm, septet, 1H
2.1 ppm, singlet, 3H
1.4 ppm, doublet, 6H
According to the IR data given, which of the following functional groups is NOT present in Compound 2?
O A. Alcohol
B. Carbon - carbon double bond
C. Ester
D. Carbon - carbon single bond
Transcribed Image Text:A flavor chemist attempted to isolate and identify the major flavor component of a recently discovered wild berry. A sample of berries was pureed in a blender , and the resulting slurry was dissolved in ethyl acetate. The solution was first extracted with 0.1 M HCI, followed by extractions with aqueous sodium bicarbonate. The ethyl acetate portion was concentrated and thin layer chromatography of the resulting oil indicated two compounds. Compound 1 with Rf of 0.2, and Compound 2 with an Rf of 0.6. The two compounds were separated by column chromatography, and the top spot (Compound 2) was identified as the essential oil. Compound 2 had the following physical characteristics: Formula: C11H1403 -1 IR: 3100, 2950, 1735, 800 cm" 1H NMR: 7.5 ppm, multiplet, 4H 4.5 ppm, septet, 1H 2.1 ppm, singlet, 3H 1.4 ppm, doublet, 6H According to the IR data given, which of the following functional groups is NOT present in Compound 2? O A. Alcohol B. Carbon - carbon double bond C. Ester D. Carbon - carbon single bond
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