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Chapter 14: Q.21558-14-4P. (page 533)

How many 1H NMR signals does each dimethylcyclopropane show?

Short Answer

Expert verified

a. 2

b. 3

c. 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

 1H 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: 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?

Question: a. How many signals does dimethyl fumarate ( CH3O2CCH=CHC02CH3 with a trans C=C) exhibit in its 13C NMR spectrum? b. Draw the structure of an isomer of dimethyl fumarate that has each of the following number of signals in its 13C NMR spectrum: [1] three; [2] four; [5] five

Question. Treatment of butan-2-one (CH3COCH2CH3) with a strong base followed by CH3l forms a compound Q, which gives a molecular ion in its mass spectrum at 86. The IR (> 1500 only) and 1H-NMR spectrum of Q is given below. What is the structure of Q?

Identify A and B, isomers of molecular formula C3H4Cl2 , from the given 1HNMR data: Compound A exhibits signals at 1.75 (doublet, 3H,J = 6.9 Hz) and 5.89 (quartet, 1H, J = 6.9 Hz) ppm. Compound B exhibits signals at 4.16 (singlet, 2 H), 5.42 (doublet, 1H, J = 1.9 Hz), and 5.59 (doublet, 1H, J = 1.9 Hz) ppm.

Rank each group of protons in order of increasing chemical shift.

a.

b.
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