13. (a) Compound C undergoes a reaction with SOC12 (or PCls) to yield compound D (Molecular Formula C₁0H₁0OCIBr) which has the following spectral data: Compound D: IR: 1685 cm ¹¹; ¹H NMR: 8 7.84 (d, J = 8 Hz, 2H), 7.60 (d, J = 8 Hz, 2H), 3.65 (t, J = 7 Hz, 2H), 3.18 (t, J = 7 Hz, 2H), 2.25 (pentet, J = 7 Hz, 2H) ppm; ¹³C NMR: d 28, 36, 45, 128, 130, 133, 137, 197 ppm; EI MS m/z: 200, 198(1:1), 185, 183 (1:1). Identify compound C from the spectral data of compound B and justify your observation.

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13. (a) Compound C undergoes a reaction with SOC12 (or PCls) to
yield compound D (Molecular Formula C₁0H₁0OCIBr)
which has the following spectral data:
Compound D: IR: 1685 cm¹; ¹H NMR: 8 7.84 (d, J = 8 Hz,
2H), 7.60 (d, J = 8 Hz, 2H), 3.65 (t, J = 7 Hz, 2H), 3.18 (t, J
= 7 Hz, 2H), 2.25 (pentet, J = 7 Hz, 2H) ppm; ¹³C NMR: d
28, 36, 45, 128, 130, 133, 137, 197 ppm; EI MS m/z: 200,
198(1:1), 185, 183 (1:1). Identify compound C from the
spectral data of compound B and justify your observation.
Transcribed Image Text:13. (a) Compound C undergoes a reaction with SOC12 (or PCls) to yield compound D (Molecular Formula C₁0H₁0OCIBr) which has the following spectral data: Compound D: IR: 1685 cm¹; ¹H NMR: 8 7.84 (d, J = 8 Hz, 2H), 7.60 (d, J = 8 Hz, 2H), 3.65 (t, J = 7 Hz, 2H), 3.18 (t, J = 7 Hz, 2H), 2.25 (pentet, J = 7 Hz, 2H) ppm; ¹³C NMR: d 28, 36, 45, 128, 130, 133, 137, 197 ppm; EI MS m/z: 200, 198(1:1), 185, 183 (1:1). Identify compound C from the spectral data of compound B and justify your observation.
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