Interpretation:
A structure for atropine (C17H23NO3) is to be proposed from the following observations: i) On basic hydrolysis atropine yields tropic acid C6H5CH(CH2OH)COOH and tropine (C8H15NO). ii) Tropine is an optically inactive alcohol that yields tropidene on dehydration with H2SO4.
Concept introduction:
Esters when hydrolyzed with bases yield alcohols and
To predict:
A structure for atropine (C17H23NO3) from the following observations: i) On basic hydrolysis atropine yields tropic acid C6H5CH(CH2OH)COOH and tropine (C8H15NO). ii) Tropine is an optically inactive alcohol that yields tropidene on dehydration with H2SO4.
Answer:
Structure of atropine is
Explanation:
Atropine gives tropic acid and an alcohol, tropine when hydrolyzed in the presence of bases. Hence it must be an ester. Tropine upon dehydration gives tropidene. Hence structure of tropine (optically inactive) can be obtained by adding water to the structure of tropidene.
The formation of the ester linkage between the OH of atropine and COOH of tropic acid gives atropine. The reactions can be represented as below.
Conclusion:
Structure of atropine is
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Chapter 24 Solutions
Organic Chemistry
- 2) (4 pt) After the reaction was completed, the student collected the following data. Crude product data is the data collected after the reaction is finished, but before the product is purified. "Pure" product data is the data collected after attempted purification using recrystallization. Student B's data: Crude product data "Pure" product data after recrystallization Crude mass: 0.93 g grey solid Crude mp: 96-106 °C Crude % yield: Pure mass: 0.39 g white solid Pure mp: 111-113 °C Pure % yield: a) Calculate the crude and pure percent yields for the student's reaction. b) Summarize what is indicated by the crude and pure melting points.arrow_forwardDon't used hand raitingarrow_forwardDon't used hand raitingarrow_forward
- Don't used hand raitingarrow_forwardShown below is the major resonance structure for a molecule. Draw the second best resonance structure of the molecule. Include all non-zero formal charges. H. H. +N=C H H H Cl: Click and drag to start drawing a structure. : ? g B S olo Ar B Karrow_forwardDon't used hand raitingarrow_forward
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