One of the compounds responsible for the odor of moist soil is geosmin, which is produced by streptomycetes in soil from farnesyl pyrophosphate, as shown in Fig. P17.43. Compounds A and B are intermediates in the biosynthesis.

Using Brønsted acids (⁺BH), Brønsted bases (B:), and water as needed, propose a curved-arrow mechanism for the conversion of compound A to geosmin with compound B as an intermediate.

Transcribed Image Text:

OPP farnesyl pyrophosphate Figure P17.43 geosmin synthase (an enzyme) OH CH3 OH CH3 geosmin CH3 H +H3C-C-CH3 acetone CH3 B