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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

Question: Label the signals due to Ha ,Hb and Hc in the 1 H NMR spectrum of acrylonitrile (CH2=CHCN ). Draw a splitting diagram for the absorption due to the proton Hc.

Compound A exhibits two signals in its 1H NMR spectrum at 2.64 and 3.69 ppm and the ratio of the absorbing signals is 2:3. Compound B exhibits two signals in its 1H NMR spectrum at 2.09 and 4.27 ppm and the ratio of the absorbing signals is 3:2. Which compound corresponds to dimethyl succinate and which compound corresponds to ethylene diacetate?

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.

Propose a structure for a compound of molecular formula C7H14O2 with an IR absorption at 1740 cm-1 and the following 1HNMR data:

AbsorptionppmRelativeareasinglet1.29triplet1.33quartet4.12

The 1H NMR spectrum of CH3OH recorded on a 500 MHz NMR spectrometer consists of two signals, one due to the CH3 protons at 1715 Hz and one due to the OH proton at 1830 Hz, both measured downfield from TMS. (a) Calculate the chemical shift of each absorption. (b) Do the CH3 protons absorb upfield or downfield from the OH proton?
See all solutions

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