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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鈥檚 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

Identify products A and B from the given \({}^{\bf{1}}{\bf{H}}\) NMR data.

(A) Treatment of \({\bf{C}}{{\bf{H}}_{\bf{2}}}{\bf{ = CHCOC}}{{\bf{H}}_{\bf{3}}}\) with one equivalent of HCl forms compound A. A exhibits the following absorptions in its \({}^{\bf{1}}{\bf{H}}\)NMR 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 \(\left( {{{\left( {{\bf{C}}{{\bf{H}}_{\bf{3}}}} \right)}_{\bf{2}}}{\bf{C = O}}} \right(\)with dilute aqueous base forms B. Compound B exhibits four singlets in its \({}^{\bf{1}}{\bf{H}}\) NMR 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?

Question: How many 13C NMR signals do each compound exhibit?

Question: A compound of molecular formula C4H802 shows no IR peaks at 3600鈥�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?

How many lines are observed in the \({}^{{\bf{13}}}{\bf{C}}\) NMR spectrum of each compound?

a.

b.

c.

d.

Label the signals due to \({{\bf{H}}_{\bf{a}}}\), \({{\bf{H}}_{\bf{b}}}\), and \({{\bf{H}}_{\bf{c}}}\) in the 1 H NMR spectrum of acrylonitrile \(\left( {{\bf{C}}{{\bf{H}}_{\bf{2}}}{\bf{ = CHCN}}} \right)\). Draw a splitting diagram for the absorption due to the \({{\bf{H}}_{\bf{c}}}\) proton.
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