A student adds caustic soda to some acetone and leaves it overnight. The next day they filter off the solid, neutralise with dilute acid, and then remove excess acetone under reduced pressure (i.e. using a rotavap). They obtain a high boiling liquid which has the 'H NMR spectrum shown below (after addition of a drop of D20). The peaks from left to right have integrations of 1:3:2:3:6 respectively. Sketch the structure of the likely product. (The spectrum can be expanded into a new window)

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter24: Amines And Heterocycles
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Problem 65AP: Phenacetin, a substance formerly used in over-the-counter headache remedies, has the formula...
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Draw the structure of the product.

A student adds caustic soda to some acetone and leaves it overnight. The next day they filter off the solid, neutralise with
dilute acid, and then remove excess acetone under reduced pressure (i.e. using a rotavap). They obtain a high boiling
liquid which has the 1H NMR spectrum shown below (after addition of a drop of D20). The peaks from left to right have
integrations of 1:3:2:3:6 respectively.
Sketch the structure of the likely product.
(The spectrum can be expanded into a new window)
1.0
3200
3.0
6|0
lle
3.5
3.0
2.5
2.0
1.5
1.0
ŏ (ppm)
Transcribed Image Text:A student adds caustic soda to some acetone and leaves it overnight. The next day they filter off the solid, neutralise with dilute acid, and then remove excess acetone under reduced pressure (i.e. using a rotavap). They obtain a high boiling liquid which has the 1H NMR spectrum shown below (after addition of a drop of D20). The peaks from left to right have integrations of 1:3:2:3:6 respectively. Sketch the structure of the likely product. (The spectrum can be expanded into a new window) 1.0 3200 3.0 6|0 lle 3.5 3.0 2.5 2.0 1.5 1.0 ŏ (ppm)
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