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Chapter 14: Q.21558-14-3P. (page 533)

How many 1H NMR signals does each compound show?

a.

b.

c.

d.

e.

f.

g.

h.

Short Answer

Expert verified

a. 2

b. 2

c. 2

d. 2

e. 4

f. 4

g. 5

h. 4

Step by step solution

01

NMR spectroscopy

Different types of proton NMR signals are observed in compounds due to the presence of different protons. The environment of these protons is affected by electron-withdrawing and electron-releasing groups.

02

 1H NMR signals in a, b, c, and d

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

Plane of symmetry in a

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

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

Plane of symmetry in b

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

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

Plane of symmetry in c

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

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

Plane of symmetry in d

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

03

 1H NMR signals in e, f, g and h

e. The given compound has four types of protons, and it will give four signals.

Structure of e

f. The given compound has four types of protons, and it will give four signals.

Structure of f

g. The given compound has five types of protons, and it will give five signals.

Structure of g

h. The given compound has four types of protons, and it will give four signals.

Structure of h

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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 1H NMR signals does each compound show? (b) Into how many peaks is each signal split?

Question: A compound of molecular formula C4H802 shows no IR peaks at 3600–3200 or 1700 cm-1 . It exhibits one singlet in its 1H NMR spectrum at 3.69 ppm, and one line in its 13C NMR spectrum at 67 ppm. What is the structure of this unknown?

Question:Reaction of unknown A with HCl forms chlorohydrin B as the major product. A shows no absorptions in its IR spectrum at 1700 cm-1 or 3600-3200 cm-1 , and gives the following 1H NMR data: 1.4 (doublet, 3 H), 3.0 (quartet of doublets, 1 H), 3.5 (doublet, 1 H), 3.8 (singlet, 3 H), 6.9 (doublet, 2 H), and 7.2 (doublet, 2 H) ppm.

(a) Propose a structure for A, including stereochemistry.

(b) Explain why B is the major product in this reaction.

Question: The 1 H NMR spectrum of N,N-dimethylformamide shows three singlets at 2.9, 3.0, and 8.0 ppm. Explain why the two groups are not equivalent to each other, thus giving rise to two NMR signals.
See all solutions

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