Nandor performed the following reaction transformation using a chiral auxiliary to promote good enantioselectivity (the preferential formation of one enantiomer over another) in his product. He reacted benzyl bromide with magnesium metal, to form an intermediate, which he reacted directly with the ketone shown below, along with a chiral auxiliary, to form the productIn a separate attempt, Nandor forgot the chiral auxiliary, but decided to finish the reaction nonetheless. He purified his product to remove any solvent, starting material and by-products, and prepared a 0.253 M solution of the target alcohol in acetone (MW = 297.44 g/mol, [α] = 114°•mL•g-1dm-1). He filled the polarimetry cell to a height of 40.5 mm. What is the angle of rotation α that he can expect to measure for the sample? BrMgchiral auxiliaryEt₂OHO-Ph

Given:Concentration of the solution = 0.253 MMolecular weight = 297.44 g/molspecific rotation, =…

Answered: Nandor performed the following reaction…

Chemistry: The Molecular Science

5th Edition

ISBN:9781285199047

Author:John W. Moore, Conrad L. Stanitski

Publisher:John W. Moore, Conrad L. Stanitski

Chapter14: Acids And Bases

Section14.9: Lewis Acids And Bases

Problem 14.26E

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Nandor performed the following reaction transformation using a chiral auxiliary to promote good enantioselectivity (the preferential formation of one enantiomer over another) in his product. He reacted benzyl bromide with magnesium metal, to form an intermediate, which he reacted directly with the ketone shown below, along with a chiral auxiliary, to form the product

In a separate attempt, Nandor forgot the chiral auxiliary, but decided to finish the reaction nonetheless. He purified his product to remove any solvent, starting material and by-products, and prepared a 0.253 M solution of the target alcohol in acetone (MW = 297.44 g/mol, [α] = 114°•mL•g^-1dm^-1). He filled the polarimetry cell to a height of 40.5 mm. What is the angle of rotation α that he can expect to measure for the sample?

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

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