Muscarine is a poisonous substance present in the mushroom Amanita muscaria. Its structure is represented by the constitution shown here. HO H3C + CH2N(CH3)3 HO¯ (a) Including muscarine, how many stereoisomers have this constitution? (b) One of the substituents on the ring of muscarine is trans to the other two. How many of the stereoisomers satisfy this requirement? (c) Muscarine has the configuration 2S,3R, 5S. Write a structural formula of muscarine showing its correct stereochemistry.

Muscarine is a poisonous substance present in the mushroom Amanita muscaria. Its structure is represented by the constitution shown here. HO H3C + CH2N(CH3)3 HO¯ (a) Including muscarine, how many stereoisomers have this constitution? (b) One of the substituents on the ring of muscarine is trans to the other two. How many of the stereoisomers satisfy this requirement? (c) Muscarine has the configuration 2S,3R, 5S. Write a structural formula of muscarine showing its correct stereochemistry.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions

Section19.SE: Something Extra

Problem 55AP: Draw and name the seven aldehydes and ketones with the formula C5H10O. Which are chiral?

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