This reaction utilizes nucleophilic substitution reactions to get from the aziridine to the oxazoline. Provide a complete arrow pushing mechanism for this transformation. You do not have to draw it while talking. You can have the mechanism already drawn out and simply talk through the steps. If you choose to use ChemDraw, be sure it is very clear where your arrows are pointing. You may also draw it by hand (paper or tablet) and screenshare an image of your work while explaining what happens. You must talk through each step of your mechanism and use proper terms such as nucleophile and electrophile.

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter20: Acidity And Pka Of Phenols
Section: Chapter Questions
Problem 11E
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1. Oxazolines (five membered ring with N and O shown below) are an important functional group
in organic chemistry because they can be used to help facilitate catalytic, enantioselective
reactions during the synthesis of important pharmaceutical molecules. One way to make
oxazolines is through the ring expansion of N-acylaziridines.
Me
Ph
Nal
Acetone
Ph
An N-Acylaziridine
An oxazoline
a. This reaction utilizes nucleophilic substitution reactions to get from the aziridine to the
oxazoline. Provide a complete arrow pushing mechanism for this transformation. You do
not have to draw it while talking. You can have the mechanism already drawn out and
simply talk through the steps. If you choose to use ChemDraw, be sure it is very clear
where your arrows are pointing. You may also draw it by hand (paper or tablet) and
screenshare an image of your work while explaining what happens. You must talk through
each step of your mechanism and use proper terms such as nucleophile and electrophile.
b. What type of substitution mechanisms are present in this reaction? How did you know?
c. Provide an explanation for the stereochemistry observed in the product. Why is it the same
as in the starting material?
d. What helps drive this reaction to favor the formation of the product?
Transcribed Image Text:1. Oxazolines (five membered ring with N and O shown below) are an important functional group in organic chemistry because they can be used to help facilitate catalytic, enantioselective reactions during the synthesis of important pharmaceutical molecules. One way to make oxazolines is through the ring expansion of N-acylaziridines. Me Ph Nal Acetone Ph An N-Acylaziridine An oxazoline a. This reaction utilizes nucleophilic substitution reactions to get from the aziridine to the oxazoline. Provide a complete arrow pushing mechanism for this transformation. You do not have to draw it while talking. You can have the mechanism already drawn out and simply talk through the steps. If you choose to use ChemDraw, be sure it is very clear where your arrows are pointing. You may also draw it by hand (paper or tablet) and screenshare an image of your work while explaining what happens. You must talk through each step of your mechanism and use proper terms such as nucleophile and electrophile. b. What type of substitution mechanisms are present in this reaction? How did you know? c. Provide an explanation for the stereochemistry observed in the product. Why is it the same as in the starting material? d. What helps drive this reaction to favor the formation of the product?
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