Problem

Propose a structure consistent with each set of spectral data:a. C4H8 Br2: IR peak at 3000...

Propose a structure consistent with each set of spectral data:

a. C4H8 Br2: IR peak at 3000–2850 cm−1; NMR (ppm):

1.87 (singlet, 6 H)

3.86 (singlet, 2 H)


b. C3H6 Br2: IR peak at 3000–2850 cm−1; NMR (ppm):

2.4 (quintet)

3.5 (triplet)


c. C5H10O2: IR peak at 1740 cm−1; NMR (ppm):

1.15 (triplet, 3 H)     1.25 (triplet, 3 H)

4.72 (quartet, 2 H)    30 (quartet, 2 H)


d. C6H14O: IR peak at 3600–3200 cm−1; NMR (ppm):

0.8 (triplet, 6 H)

1.5 (quartet, 4 H)

1.0 (singlet, 3 H)

1.6 (singlet, 1 H)

e. C6H14O: IR peak at 3000–2850 cm−1; NMR (ppm):

1.10 (doublet, 30 units)

3.60 (septet, 5 units)


f. C3H6O: IR peak at 1730 cm−1; NMR (ppm):

1.11 (triplet)

2.46 (multiplet)

9.79 (triplet)

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