O Draw chemical structures from B to G to complete the following reaction scheme. The starting compound B shows three singlets in a 'H NMR experiment with chemical shifts of 3.72 ppm, 3.49 ppm, and 2.26 ppm using tetramethylsilane as an internal standard in deuterated chloroform. The respective ratio of integration is 3: 2:3. Furthermore, compound B is positive for the iodoform test. B C5H₂O3 HCI, H₂O E heat H3C CH3 1. CH₂O (1.0 equivalent) 2. CH3Br (1.0 equivalent) HCI, H₂O heat F LL OH™ C 12 (excess) H3O+ heat OH™ (excess) SOCI₂ CH3OH D G C4H8O2

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O Draw chemical structures from B to G to complete the following reaction scheme.
The starting compound B shows three singlets in a 'H NMR experiment with
chemical shifts of 3.72 ppm, 3.49 ppm, and 2.26 ppm using tetramethylsilane as an
internal standard in deuterated chloroform. The respective ratio of integration is 3:
2: 3. Furthermore, compound B is positive for the iodoform test.
B
C5H8O3
HCI, H₂O
E
heat H₂C CH3
1. CH3O (1.0 equivalent)
2. CH3Br (1.0 equivalent)
HCI, H₂O
heat
F
OH™
OH™
(excess)
12
(excess)
C
H3O+
heat
SOCI₂ CH3OH
D
G
C4H8O2
Transcribed Image Text:O Draw chemical structures from B to G to complete the following reaction scheme. The starting compound B shows three singlets in a 'H NMR experiment with chemical shifts of 3.72 ppm, 3.49 ppm, and 2.26 ppm using tetramethylsilane as an internal standard in deuterated chloroform. The respective ratio of integration is 3: 2: 3. Furthermore, compound B is positive for the iodoform test. B C5H8O3 HCI, H₂O E heat H₂C CH3 1. CH3O (1.0 equivalent) 2. CH3Br (1.0 equivalent) HCI, H₂O heat F OH™ OH™ (excess) 12 (excess) C H3O+ heat SOCI₂ CH3OH D G C4H8O2
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