Shown are both conformers of menthyl chloride, a diastereomer of neomenthyl chloride. CH3 H H3C CH. H H. H- H3C CI- D CH3 H CH CH3 H3C H c. Which of the two conformers is more stable (C or D)? d. Which will eliminate with CH3CH20 in refluxing ethanol (C or D)? When menthyl chloride reacts with ethoxide (CH3CH20-), only one alkene is formed and it is NOT the alkene predicted by Zaitsev's rule. Draw the structure of this alkene. On C or D (pictured above, whichever is appropriate) circle the proton that is removed in this reaction.

Shown are both conformers of menthyl chloride, a diastereomer of neomenthyl chloride. CH3 H H3C CH. H H. H- H3C CI- D CH3 H CH CH3 H3C H c. Which of the two conformers is more stable (C or D)? d. Which will eliminate with CH3CH20 in refluxing ethanol (C or D)? When menthyl chloride reacts with ethoxide (CH3CH20-), only one alkene is formed and it is NOT the alkene predicted by Zaitsev's rule. Draw the structure of this alkene. On C or D (pictured above, whichever is appropriate) circle the proton that is removed in this reaction.

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter6: Alkanes & Alkenes

Section: Chapter Questions

Problem 2E

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