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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

Propose a structure for a compound of molecular formula C3H8O with an IR absorption at 3600 to 3200 cm-1 and the following NMR spectrum:

Identify the carbon atoms that give rise to the signals in the \)^{{\bf{13}}}{\bf{C}}\) NMR spectrum of each compound.

a. \){\bf{C}}{{\bf{H}}_{\bf{3}}}{\bf{C}}{{\bf{H}}_{\bf{2}}}{\bf{C}}{{\bf{H}}_{\bf{2}}}{\bf{C}}{{\bf{H}}_{\bf{2}}}{\bf{OH}}\); \)^{{\bf{13}}}{\bf{C}}\) NMR: 14, 19, 35, and 62 ppm

b. \){\left( {{\bf{C}}{{\bf{H}}_{\bf{3}}}} \right)_{\bf{2}}}{\bf{CHCHO}}\); \)^{{\bf{13}}}{\bf{C}}\) NMR: 16, 41, and 205 ppm

c. \){\bf{C}}{{\bf{H}}_{\bf{2}}}{\bf{ = CHCH}}\left( {{\bf{OH}}} \right){\bf{C}}{{\bf{H}}_{\bf{3}}}\); \)^{{\bf{13}}}{\bf{C}}\) NMR: 23, 69, 113, and 143 ppm

Question. Compound O has a molecular formula C10H12O and shows an IR absorption at 1687 . The 1H -NMR spectrum of O is given below. What is the structure of O?

Question: Reaction of C6H5CH2CH2OH with CH3COCl affords compound W, which has molecular formula C10H12O2. W shows prominent IR absorptions at 3088–2897, 1740, and 1606cm-1 . W exhibits the following signals in its 1 H NMR spectrum: 2.02 (singlet), 2.91 (triplet), 4.25 (triplet), and 7.20–7.35 (multiplet) ppm. What is the structure of W? We will learn about this reaction in Chapter 22.

For each compound, which of the protons on the highlighted carbons absorbs farther downfield?

a.

b.

c.

See all solutions

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