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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

Draw all constitutional isomers of molecular formula C3H6Cl2.

a. How many signals does each isomer exhibit in its 1HNMR spectrum?

b.How many lines does each isomer exhibit in its 13CNMR spectrum?

c. When only the number of signals in both 1Hand 13C NMR spectroscopy is considered, is it possible to distinguish all of these constitutional isomers?

Question: How many different types of protons are present in each compound?

Question: 18-Annulene shows two signals in its 1 H NMR spectrum, one at 8.9 (12 H) and one at 鈥�1.8 (6 H) ppm. Using a similar argument to that offered for the chemical shift of benzene protons, explain why both shielded and deshielded values are observed for 18-annulene.

Question: Propose a structure consistent with each set of data.

a. A compound X (molecular formula C6H12O2) gives a strong peak in its IR spectrum at 1740 cm-1. The 1 H NMR spectrum of X shows only two singlets, including one at 3.5 ppm. The 13C NMR spectrum is given below Propose a structure for X.

b. A compound Y (molecular formula C6H10 ) gives four lines in its 13C NMR spectrum (27, 30, 67, and 93 ppm), and the IR spectrum given here. Propose a structure for Y.

Question: Identify the structures of isomers A and B (molecular formula C9H10O ).

Compound A: IR peak at 1742 cm-1 ; 1 H NMR data (ppm) at 2.15 (singlet, 3 H), 3.70 (singlet, 2 H), and 7.20 cm-1(broad singlet, 5 H). Compound B: IR peak at 1688 ; 1 H NMR data (ppm) at 1.22 (triplet, 3 H), 2.98 (quartet, 2 H), and 7.28鈥�7.95 (multiplet, 5 H).
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