Attached is the 13C-NMR Spectrum of 1,2,3,4-tetraphenylnapthalene (CDCl3)Can you provide (chemical shift (experimental),chemical shift (literature), assignment) Chemical shift δ(ppm)Experimental Chemical shift δ(ppm) LiteratureAssignment 13C-NMR Spectrum• In solution: Thirteen signals because1. 2. 3, 4-Tetraphenyinaphthalenewe assume a free rotation about theo-bonds (marked in red) resulting ina high (apparent) degree of symmetry.Overlap oftwo tall signalsIpso: five small signals (no H-atom)Ortho/meta: four large signals (2 each)Para/naphthalene: four mediumsignals (1 each)• In solid: At least seventeen signalsbecause of the hindered (slow) rotationabout the o-bonds leads to lower140135130degree of symmetry in the phenyl rings(six signals instead of four signals asexpected for mono-substituted phenylring because of the hindered rotation).TeteaphanylnapshanieneT|||||| |21Sasotution Enhancedwwwwmww10ils140132 13C-NMR Spectrum (CDC13)1, 2, 3, 4-Tciraphenylnaphthaleneoverlap of twotall signals125114013513040.571-129.628-138.922-138.453F132.070131.346----127.E75/127.33:~-126 518-126 470125.927:25.380

The peaks of the structure is assigned below:

Attached is the 13C-NMR Spectrum of 1,2,3,4-tetraphenylnapthalene (CDCl3) Can you provide (chemical shift (experimental), chemical shift (literature), assignment) Chemical shift δ(ppm) Experimental Chemical shift δ(ppm) Literature Assignmen

Attached is the 13C-NMR Spectrum of 1,2,3,4-tetraphenylnapthalene (CDCl3) Can you provide (chemical shift (experimental), chemical shift (literature), assignment) Chemical shift δ(ppm) Experimental Chemical shift δ(ppm) Literature Assignmen

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter30: Orbitals And Organic Chemistry: Pericyclic Reactions

Section30.SE: Something Extra

Problem 37AP: The 1H NMR spectrum of bullvalene at 100 C consists only of a single peak at 4.22 . Explain.

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Question

Attached is the 13C-NMR Spectrum of 1,2,3,4-tetraphenylnapthalene (CDCl3)

Can you provide (chemical shift (experimental),
chemical shift (literature), assignment)

Chemical shift δ(ppm) Experimental	Chemical shift δ(ppm) Literature	Assignment

13C-NMR Spectrum
• In solution: Thirteen signals because
1. 2. 3, 4-Tetraphenyinaphthalene
we assume a free rotation about the
o-bonds (marked in red) resulting in
a high (apparent) degree of symmetry.
Overlap of
two tall signals
Ipso: five small signals (no H-atom)
Ortho/meta: four large signals (2 each)
Para/naphthalene: four medium
signals (1 each)
• In solid: At least seventeen signals
because of the hindered (slow) rotation
about the o-bonds leads to lower
140
135
130
degree of symmetry in the phenyl rings
(six signals instead of four signals as
expected for mono-substituted phenyl
ring because of the hindered rotation).
Teteaphanylnapshaniene
T|||||| |21
Sasotution Enhanced
wwwwmww
10
ils
140
132

13C-NMR Spectrum (CDC13)
1, 2, 3, 4-Tciraphenylnaphthalene
overlap of two
tall signals
125
1
140
135
130
40.571
-129.628
-138.922
-138.453
F132.070
131.346
----127.E75
/127.33:
~-126 518
-126 470
125.927
:25.380

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