Chemistry
Organic Chemistry
Ambrettolide is obtained from hibiscus and has a musk-like odor.

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

Question:

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

Transcribed Image Text:

HoC(CH2CH-CH(CH2 CH2OH> 1 0 CH CH Compound A Ambrettolide Step Reactant Compound A Compound B Compound C Compound D Compound E Compound F Compound G Reagents H20, H, heat HBr Ethanol, H2504 Zinc, ethanol Sodium acetate, acetic acid KOH, ethanol, then H' Heat Product Compound B (C 16H3205) Compound C 2. (C16H29Br3O2) (С 18H33Br3O2) (C 18H 33B rO2) Compound D 4 Compound E Compound F (C20H3604) Compound G (C16H3003) Ambrettolide (C16H282, 6

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Organic Chemistry

ISBN: 978-0072905014

4th edition

Authors: Francis A. Carey

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Question Posted: Apr 30, 2016 01:49 PM

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