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Chapter 14: Q3P (page 527)

Question: How many \(^{\bf{1}}{\bf{H}}\) NMR signals does each compound show?

a.

b.

c.

d.

e.

f.

g.

h.

Short Answer

Expert verified

  1. 2

  2. 2

  3. 2

  4. 2

  5. 4

  6. 4

  7. 5

  8. 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

Step 2: \(^{\bf{1}}{\bf{H}}\) 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

Step 3: \(^{\bf{1}}{\bf{H}}\) 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

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

a.

b.

c.

d.

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.

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.

Label the protons in each highlighted CH2 group as enantiotopic, diastereotopic, or homotopic.

a.

b.

c.

Draw all constitutional isomers of molecular formula \({{\bf{C}}_{\bf{3}}}{{\bf{H}}_{\bf{6}}}{\bf{C}}{{\bf{l}}_{\bf{2}}}\).

a. How many signals does each isomer exhibit in its \({}^{\bf{1}}{\bf{H}}\) NMR spectrum?

b. How many lines does each isomer exhibit in its \({}^{{\bf{13}}}{\bf{C}}\) NMR spectrum?

c. When only the number of signals in both \({}^{\bf{1}}{\bf{H}}\) and \({}^{{\bf{13}}}{\bf{C}}\) NMR spectroscopy is considered, is it possible to distinguish all of these constitutional isomers?
See all solutions

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