(a) An unknown compound A has the formula C₇H₁₂O₂ and infrared spectrum A (p. 917). To which class does this compound belong? 

(b) Use the other spectra (NMR-B, p. 917, and F, p. 919; IR-D, E, and F, pp. 918 – 919) and spectroscopic and chemical information in the reaction sequence to determine the structures of compound A and the other unknown substances B through F. References are made to relevant sections of earlier chapters, but do not look them up before you have tried to solve the problem without the extra help. 

(c) Another unknown compound, G, has the formula C₈H₁₄O₄ and the NMR and IR spectra labeled G (p. 920). Propose a structure for this molecule. 

(d) Compound G may be readily synthesized from B. Propose a sequence that accomplishes this efficiently. 

(e) Propose a completely different sequence from that shown in (b) for the conversion of C into A. 

(f) Finally, construct a synthetic scheme that is the reverse of that shown in (b); namely, the conversion of A into B. 

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1. Hg(ОССH)» Н,о 2. NABH, CrO, H,SO, acetone, 0°C C6H10 C6H120 Section 12-7 Section 8-6 в C "C NMR: 6 = 22.1 "C NMR: 6 = 24.4 24.5 25.9 126.2 ppm 35.5 'H NMR-B 69.5 ppm