Answered: 17) After the reaction, Gwen sees a…

17) After the reaction, Gwen sees a solid appear. She should collect this solid by rotary evaporator vacuum filtration TLC gravity filtration

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter25: Enolate & Enol Nucleophiles

Section: Chapter Questions

Problem 20E

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Question

17) After the reaction, Gwen sees a solid appear. She should collect this solid by

rotary evaporator

vacuum filtration

TLC

gravity filtration

18) After completing the separation and purification, Gwen checks the purity of her isolated mandelic acid on a polarimeter. She takes 0.525 g of solid and dissolves it in 5 mL of acetone. She puts this in a tube with a pathlength of 1 dm. The polarimeter gives a reading of +13.0011 deg.

The reported optical activity of mandelic acid is [a]lit = 151 deg

What is the EE for this sample?

Resolution of Enantiomers
Gwen needs S-(+)-mandelic acid for a project, but she only has a bottle of racemic mandelic
acid to work with. She finds a bottle of L-(-)-proline and comes up with a plan to isolate S-(+)-
mandelic acid.
of-oror
(RS)-mandelic acid
HO
OH
HN
OH
L-(-)-proline
OH
R-(-)-mandelic acid
OH
S-(+)-mandelic acid
OH

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