Treatment of compound A (C8H17Br) with NaOCH2CH3 affords twoconstitutional isomers B and C. Ozonolysis of B affords CH2=O and(CH3CH2CH2)2C=O. Ozonolysis of C affords CH3CH2CH2COCH3 andCH3CH2CHO. What is the structure of A?

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter24: Amines And Heterocycles
Section24.10: Spectroscopy Of Amines
Problem 25P
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Treatment of compound A (C8H17Br) with NaOCH2CH3 affords two
constitutional isomers B and C. Ozonolysis of B affords CH2=O and
(CH3CH2CH2)2C=O. Ozonolysis of C affords CH3CH2CH2COCH3 and
CH3CH2CHO. What is the structure of A?

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