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Chapter 14: Q.21558-14-5P. (page 534)

How many NMR signals does each compound give?

a.

b.

c.

d.

Short Answer

Expert verified

a. 3

b. 4

c. 5

d. 3

Step by step solution

01

NMR spectroscopy

The chemical shift’s value of a proton depends on the type of atom attached to it. If it is attached to an electronegative atom, the value of the chemical shift increases.

02

 1H NMR signals in a and b

a.

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

Structure of a

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

b.

The given compound has four types of protons, and it will give four signals, as shown below.

Structure of b

03

 1H NMR signals in c and d

c.

The given compound has five types of protons, and it will give five signals, as shown below.

Structure of c

d.

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

Structure of d

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

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Most popular questions from this chapter

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.

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:

Rank the highlighted carbon atoms in each compound in order of increasing chemical shift.

a.

b.

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?

Label each statement as True or False.

a. When a nucleus is strongly shielded, the effective field is larger than the applied field and the absorption shifts downfield.

b. When a nucleus is strongly shielded, the effective field is smaller than the applied field and the absorption is shifted upfield.

c. A nucleus that is strongly deshielded requires a lower field strength for resonance.

d. A nucleus that is strongly shielded absorbs at a larger δ value.
See all solutions

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