Provide the structure of the unknown compound from the given information. 
Formula:C₄H₁₀O            IR:3200-3600 cm^{-1           1}H NMR:0.9 ppm (6H, doublet) 
                                                                                               1.8 ppm (1H, nonatet) 
                                                                                               2.4 ppm (1H, singlet) 
                                                                                               3.3 ppm (2H, doublet)

Propose a structure for the following compound that fits the following 1H NMR data: 

Formula:C₃H₈O₂                                                  ¹H NMR:3.36 δ (6H, singlet) 

                                                                                         4.57 δ (2H, singlet)

Propose a structure for the following compound that fits the following ¹H NMR data: 

Formula:C₂H₄O₂                                            ¹H NMR:2.1 δ (singlet, 1.2 cm) 

                                                                                   11.5 δ (0.5 cm, D2O exchange)

Propose a structure for the following compound that fits the following ¹H NMR data: 

Formula:C₁₀H₁₄                                      ¹H NMR:1.2 ppm (6H, doublet) 

                                                                             2.3 ppm (3H, singlet) 

                                                                             2.9 ppm (1H, septet) 

                                                                             7.0 ppm (4H, doublet)

Propose a structure for the following compound, C₅H₁₀O with the given ¹³C NMR spectral data: 

Fully Broadband decoupled ¹³C NMR and DEPT:206.0 δ (↑); 55.0 δ (↑); 21.0 δ (↓)& 11.0 δ (↑).

Provide the structure of the unknown compound from the given information. 

Formula:C₄H₉N              IR:2950 cm^-1, 3400 cm^{-1           1}H NMR:1.0 ppm (4H, triplet) 

                                                                                                         2.1 ppm (4H, triplet) 

                                                                                                         3.2 ppm (1H, singlet)

Show how you would distinguish among the following three compounds

(a) using infrared spectroscopy and no other information.

(b) using proton NMR spectroscopy and no other information.

(c) using ¹³C NMR, including DEPT, and no other information.

When 2-chloro-2-methylbutane is treated with a variety of strong bases, the products always seem to contain two isomers (A and B) of formula C₅H₁₀. When sodium hydroxide is used as the base, isomer A predominates. When potassium tert-butoxide is used as the base, isomer B predominates. The ¹H and ¹³C NMR spectra of A and B are given below.

(a) Determine the structures of isomers A and B.

(b) Explain why A is the major product when using sodium hydroxide as the base and why B is the major product when using potassium tert-butoxide as the base.

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A compound of molecular formula C₈H₈O gives the IR and NMR spectra shown here. Propose a structure, and show how it is consistent with the observed absorptions.

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