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Chapter 14: Q4P (page 527)

Question: How many \(^{\bf{1}}{\bf{H}}\) NMR signals does each dimethylcyclopropane show?

a.

b.

c.

Short Answer

Expert verified
  1. 2
  2. 3
  3. 3

Step by step solution

01

NMR spectroscopy

If a compound contains either plane of symmetry or center of symmetry, the protons of the opposite (mirror images) substituents have the same environment. Thus, these protons have given the same signal.

02

Step 2: \(^{\bf{1}}{\bf{H}}\) NMR signals in a, b, and c

a. The given compound has a plane of symmetry as shown below:

Plane of symmetry in a

Thus, the given compound has two types of protons, and it will provide two signals.

b. The given compound has a plane of symmetry as shown below:

Plane of symmetry in b

Thus, the given compound has three types of protons, and it will provide three signals.

c. The given compound has a center of symmetry as shown below:

Center of symmetry in c

Thus, the given compound has three types of protons, and it will provide three signals.

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Most popular questions from this chapter

Question: Using a 300 MHz NMR instrument:

a. How many Hz downfield from TMS is a signal at 2.5 ppm?

b. If a signal comes at 1200 Hz downfield from TMS, at what ppm does it occur?

c. If two signals are separated by 2 ppm, how many Hz does this correspond to?

Question. Compound Q has molecular formula C5H9CIO2. Deduce the structure of P from its 1H and 13C -NMR spectra.

Draw all constitutional isomers of molecular formula \({{\bf{C}}_{\bf{3}}}{{\bf{H}}_{\bf{6}}}{\bf{C}}{{\bf{l}}_{\bf{2}}}\).

a. How many signals does each isomer exhibit in its \({}^{\bf{1}}{\bf{H}}\) NMR spectrum?

b. How many lines does each isomer exhibit in its \({}^{{\bf{13}}}{\bf{C}}\) NMR spectrum?

c. When only the number of signals in both \({}^{\bf{1}}{\bf{H}}\) and \({}^{{\bf{13}}}{\bf{C}}\) NMR spectroscopy is considered, is it possible to distinguish all of these constitutional isomers?

Question: Because 31P has an odd mass number, 31P nuclei absorb in the NMR and, in many ways, these nuclei behave similarly to protons in NMR spectroscopy. With this in mind, explain why the 1 H NMR spectrum of methyl dimethyl phosphonate,CH3PO(OCH3)2 , consists of two doublets at 1.5 and 3.7 ppm.

Question: The \(^{\bf{1}}{\bf{H}}\) NMR spectrum 1,2-dimethoxyethane \(\left( {{\bf{C}}{{\bf{H}}_{\bf{3}}}{\bf{OC}}{{\bf{H}}_{\bf{2}}}{\bf{C}}{{\bf{H}}_{\bf{2}}}{\bf{OC}}{{\bf{H}}_{\bf{3}}}} \right)\) recorded on a 300 MHz NMR spectrometer consists of signals at 1017 Hz and 1065 Hz downfield from TMS. (a) Calculate the chemical shift of each absorption. (b) At what frequency would each absorption occur if the spectrum were recorded on a 500 MHz NMR spectrometer?
See all solutions

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