Question

Provide the most likely chemical structure that corresponds to each set of spectral data (2.5 pts each). Please show your work, though: even if you do not arrive at the correct answer, you can earn partial credit.

1. Formula: C₆H₁₂

IR: 2965 cm^-1(strong), 3028 cm^-1(medium)

¹H NMR: 6H, triplet (1.0 ppm); 4H, quintet (1.8 ppm); 2H, triplet (5.4 ppm)

¹³C NMR: 22 ppm, 39 ppm, 125 ppm

2. Formula: C₆H₁₂O

IR: 2960 cm^-1(strong), 2874 cm^-1(medium), 1716 cm^-1(strong, sharp)

¹H NMR: 2H, doublet (2.312 ppm); 1H, multiplet (2.133 ppm); 3H, singlet (2.123 ppm);

6H, doublet (0.926 ppm)

¹³C NMR: 208 ppm, 53 ppm, 30 ppm, 24 ppm, 22 ppm

3. Formula: C₄H₁₀O

IR: 3339 cm^-1(broad, strong), 2957 cm^-1(strong), 2874 cm^-1(medium)

¹H NMR: 6H, doublet (0.9 ppm); 1H, nonet (1.75 ppm); 2H, doublet (3.35 ppm);

1H, singlet (3.9 ppm)

¹³C NMR: 3 peaks

4. Formula: C₉H₁₀O₂

IR: 1718 cm^-1(sharp, strong)

¹H NMR: 3H, triplet (1.35 ppm); 2H, quartet (4.40 ppm);

5H, multiplet (7.40 ppm, 7.55 ppm, 8.10 ppm)

My professor posted this this week for us to finish and turn in by Friday. Our Lab course is currently online and I am having a very difficult time figuring this out. Thanks in Advance!