Treatment of (CH3)2CHCH(OH)CH2CH3 with TsOH affords two products(M and N) with molecular formula C6H12. The 1H NMR spectra of M and Nare given below. Propose structures for M and N, and draw a mechanismto explain their formation. P.mr rd...d.. ..rar l all. a.. lul l..ll.l.aCullano: IR peak at 26 DO 200 em-1: NMR (Ppm):0.0 (triplet. GI) 1.5 (quartet. 4I1)Rpeuk al 30D0 285o em-4: NMR (Pin):1.10 (dc bkt. reltive ureu - 5).lal -1 >H NMR of M3 HH NMR of N3H3H3H1H3H2H2 H2 H2H9.49876pnmnpm

Given: When (CH3)2CHCH(OH)CH2CH3 is treated with TsOH, the products M and N having molecular formula…

P.mr rd...d.. ..rar l all. a.. lul l..ll.l. aCullano: IR peak at 26 DO 200 em-1: NMR (Ppm): 0.0 (triplet. GI) 1.5 (quartet. 4I1) Rpeuk al 30D0 285o em-4: NMR (Pin): 1.10 (dc bkt. reltive ureu - 5) .lal -1 > H NMR of M 3 H H NMR of N 3H 3H 3H 1H 3H 2H 2 H 2 H 2H 9. 4 9 8 7 6 pnm npm

P.mr rd...d.. ..rar l all. a.. lul l..ll.l. aCullano: IR peak at 26 DO 200 em-1: NMR (Ppm): 0.0 (triplet. GI) 1.5 (quartet. 4I1) Rpeuk al 30D0 285o em-4: NMR (Pin): 1.10 (dc bkt. reltive ureu - 5) .lal -1 > H NMR of M 3 H H NMR of N 3H 3H 3H 1H 3H 2H 2 H 2 H 2H 9. 4 9 8 7 6 pnm npm

Principles of Instrumental Analysis

7th Edition

ISBN:9781305577213

Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch

Publisher:Douglas A. Skoog, F. James Holler, Stanley R. Crouch

Chapter19: Nuclear Magnetic Resonance Spectroscopy

Section: Chapter Questions

Problem 19.3QAP

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Concept explainers

NMR Spectroscopy

NMR stands for Nuclear Magnetic Resonance in which the study of different molecules is done based on the interaction of radiofrequency electromagnetic radiations with the nuclei of molecules placed in a strong magnetic field. A precise study of spectra of visible light and all bands of electromagnetic radiation is called spectroscopy.

Question

100%

Treatment of (CH₃)₂CHCH(OH)CH₂CH₃ with TsOH affords two products
(M and N) with molecular formula C₆H₁₂. The ¹H NMR spectra of M and N
are given below. Propose structures for M and N, and draw a mechanism
to explain their formation.

P.mr rd...d.. ..rar l all. a.. lul l..ll.l.
aCullano: IR peak at 26 DO 200 em-1: NMR (Ppm):
0.0 (triplet. GI) 1.5 (quartet. 4I1)
Rpeuk al 30D0 285o em-4: NMR (Pin):
1.10 (dc bkt. reltive ureu - 5)
.lal -1 >
H NMR of M
3 H
H NMR of N
3H
3H
3H
1H
3H
2H
2 H
2 H
2H
9.
4
9
8
7
6
pnm
npm

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