Chapter 3.10, Problem 36ATS

11 8. When benzene is treated with Reagent(s) A followed by Reagent(s) B, Compound P (CaHCIO) is the major product. If the order of reagents is reversed, Compound Q (also CaHCIO) is formed instead (see the scheme below). Both P and Q have a strong IR absorption around 1685 cm, H and "C NMR spectra of P and Q are shown below. Draw the structures of P and Q and list the Reagents A and B. Benzene 10 1. A 2. B 9 Compound P ¹H NMR Compound Q ¹H NMR 2:2 السر 2:1:1 ppm 5 ppm : 3 3 Benzene DEPT-90 DEPT-135 0 DEPT-90 200 180 200 DEPT-135 1. B 2. A 180 160 160 140 12 140 120 120 100 ppm Compound P 13C NMR 2 peaks 60 BO Compound Q 13C NMR 100 ppm 80 60 40 -8 20 20

Muscalure, the sex pheromone of the common housefly, can be prepared by a reaction sequence that uses two nucleophilic substitutions. Identify compounds A-D in the following synthesis of muscalure. NaH CH3(CH2),CH,Br A NaH H-C=C-H в H2 + + H2 CHg(CH2)11CH2B H H addition of H2 C=C D CH3(CH2),CH2 CH2(CH2)1,CHg (1 equiv) muscalure

The sex attractant of the female winter moth has been identified as the tetraene CH3(CH2)8CH=CHCH2CH=CHCH2CH=CHCH=CH2. Devise a synthesis of this material from 3,6-hexadecadien-1-ol and allyl alcohol.