Problem

Ambrettolide is obtained from hibiscus and has a musk-like odor. Its preparation from comp...

Ambrettolide is obtained from hibiscus and has a musk-like odor. Its preparation from compound A is outlined in the table that follows. Write structural formulas, ignoring stereochemistry, for compounds B through G in this synthesis. (Hint: Zinc, as used in step 4, converts vicinal dibromides to alkenes.)

Step	Reactant	Reagents	Product
1.	Compound A	H2O, H+heat	Compound B (C16H32O5)
2.	Compound B	HBr	Compound C (C16H29Br3O2)
3.	Compound C	Ethanol, H2SO4	Compound D (C18H33Br3O2)
4.	Compound D	Zinc, ethanol	Compound E (C18H33BrO2)
5.	Compound E	Sodium acetate, acetic acid	Compound F (C20H36O4)
6.	Compound F	KOH, ethanol, then H +	Compound G (C16H3O3)
7.	Compound G	Heat	Ambrettolide (C16H28O2)

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Solutions For Problems in Chapter 19

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