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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 consistent with each set of data.

a. C9H10O2: IR absorption at 1718cm-1

b. C9H12 : IR absorption at 2850–3150cm-1

The reaction of (CH3)3 CCHO with (C6H5)3 P=C(CH3)OCH3 , followed by treatment with aqueous acid, afford R . R has strong absorption in its IR spectrum at 1717 cm-1 and three singlets in its -NMR spectrum at 1.02 (9 H), 2.13 (3 H), and 2.33 (2 H) ppm. What is the structure of R? We will learn about this reaction in Chapter 21.

Identify products A and B from the given 1HNMR data.

a. Treatment of CH2=CHCOCH3 with one equivalent of HCl forms compound A. A exhibits the following absorptions in its 1HNMR spectrum: 2.2 (singlet, 3 H), 3.05 (triplet, 2 H), and 3.6 (triplet, 2H) ppm. What is the structure of A?

b.Treatment of acetone [(CH3)2C=O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1HNMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1 H) ppm. What is the structure of B?

What splitting pattern is observed for each proton in the following compounds?

a.

b.

How many peaks are present in the NMR signal of each labelled proton?

a.

b.

c.

d.
See all solutions

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