: Treatment of (CHa)CHCH(OH)CH,CH3 with TSOH affords two products (M and N) with molecular formula CgH12. The 'H NMR spectra of M and N are given below. Propose structures for M and N and draw a mechanism to explain their formation. 1H NMR of M 3H 1H NMR of N 3H 3H 3 H 1H 3 H 2 H 2H 2H 8 7 6 4 1 0 9 8. 2 1 ppm ppm 4.

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter9: Nucleophilic Substitution And Β-elimination
Section: Chapter Questions
Problem 9.16P: Treatment of 1-aminoadamantane, C10H17N, with methyl 2,4-dibromobutanoate in the presence of a...
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: Treatment of (CHa)CHCH(OH)CH,CH3 with TSOH affords two products (M and N) with molecular formula CgH12. The 'H NMR
spectra of M and N are given below. Propose structures for M and N and draw a mechanism to explain their formation.
1H NMR of M
3H
1H NMR of N
3H
3H
3 H
1H
3 H
2 H
2H
2H
8
7
6
4
1
0 9
8.
2
1
ppm
ppm
4.
Transcribed Image Text:: Treatment of (CHa)CHCH(OH)CH,CH3 with TSOH affords two products (M and N) with molecular formula CgH12. The 'H NMR spectra of M and N are given below. Propose structures for M and N and draw a mechanism to explain their formation. 1H NMR of M 3H 1H NMR of N 3H 3H 3 H 1H 3 H 2 H 2H 2H 8 7 6 4 1 0 9 8. 2 1 ppm ppm 4.
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