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)

Identify each of the following compounds from its molecular formula and its IR and ¹H NMR spectra:

b.C₆H₁₄O

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A compound with molecular formula C₅H₁₀O₂ gives the following IR spectrum. When it undergoes acid-catalyzed hydrolysis, the compound with the ¹H NMR spectrum shown below is formed. Identify the compounds.

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An unknown compound (C₃H₂NCl) shows moderately strong IR absorptions around 1650 cm^–1 and 2200 cm^–1. Its NMR spectrum consists of two doublets (J = 14 Hz) at δ5.9 and δ7.1. Propose a structure consistent with these data.

Identify each of the following compounds from its molecular formula and its IR and ¹H NMR spectra.

d. C₄H₈O₂

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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: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)