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Chapter 14: Q5P (page 527)

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

a.

b.

c.

d.

Short Answer

Expert verified
  1. 3
  2. 4
  3. 5
  4. 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

Step 2: \(^{\bf{1}}{\bf{H}}\) 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

Step 3: \(^{\bf{1}}{\bf{H}}\) 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

Propose a structure consistent with each set of data.

a. C9H10O2: IR absorption at 1718cm-1

b. C9H12 : IR absorption at 2850–3150cm-1

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

a.

b.

c.

Identify products A and B from the given 1HNMR data.

a. Treatment of CH2=CHCOCH3 with one equivalent of HCl forms compound A. A exhibits the following absorptions in its 1HNMR spectrum: 2.2 (singlet, 3 H), 3.05 (triplet, 2 H), and 3.6 (triplet, 2H) ppm. What is the structure of A?

b.Treatment of acetone [(CH3)2C=O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1HNMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1 H) ppm. What is the structure of B?

Identify the carbon atoms that give rise to the signals in the \)^{{\bf{13}}}{\bf{C}}\) NMR spectrum of each compound.

a. \){\bf{C}}{{\bf{H}}_{\bf{3}}}{\bf{C}}{{\bf{H}}_{\bf{2}}}{\bf{C}}{{\bf{H}}_{\bf{2}}}{\bf{C}}{{\bf{H}}_{\bf{2}}}{\bf{OH}}\); \)^{{\bf{13}}}{\bf{C}}\) NMR: 14, 19, 35, and 62 ppm

b. \){\left( {{\bf{C}}{{\bf{H}}_{\bf{3}}}} \right)_{\bf{2}}}{\bf{CHCHO}}\); \)^{{\bf{13}}}{\bf{C}}\) NMR: 16, 41, and 205 ppm

c. \){\bf{C}}{{\bf{H}}_{\bf{2}}}{\bf{ = CHCH}}\left( {{\bf{OH}}} \right){\bf{C}}{{\bf{H}}_{\bf{3}}}\); \)^{{\bf{13}}}{\bf{C}}\) NMR: 23, 69, 113, and 143 ppm

Sketch the NMR spectrum of CH3CH2Cl , giving the approximate location of each NMR signal.
See all solutions

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