Answered: 2-Acetnaphthone NaBH4 CH₂OH Product A…

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2-Acetnaphthone NaBH4 CH₂OH Product A OH or Product B ?

Introduction to General, Organic and Biochemistry

11th Edition

ISBN:9781285869759

Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Chapter16: Amines

Section: Chapter Questions

Problem 16.39P

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Concept explainers

Alkanes and Cycloalkanes

Alkanes are saturated organic compounds which are made up of C and H atoms. Alkanes have the general formula of CnH2n+2. Alkane contains sp3 hybridized carbon atoms with four sigmas (σ) bonds & every hydrogen atom is connected with one of the carbon atoms. The size of the alkane could be determined by the number of carbon atoms located in it.

Question

Take a look at the reaction in the first image that give two products A and B

The second picture shows the DEPT 90 (TOP) and DEPT 135 (BOTTOM) of the compound that was isolated as only product of this reaction:

In both spectra there are 7 signals between 120 and 140 ppm.

How can you use these DEPT spectra to establish if product A or product B was formed in this reaction? Explain your reasoning.

200
150
100
50
0 [ppm]
0 2
4
4
6 8
10
12 14 [rel]
DEPT 135 spectrum)
200
150
100
50
0 [ppm]
0
2
4 6 8
10 12
14 [r

2-Acetnaphthone
NaBH4
CH3OH
Product A
OH
or
Product B
?

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