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Chapter 14: Q4P (page 527)

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

a.

b.

c.

Short Answer

Expert verified
  1. 2
  2. 3
  3. 3

Step by step solution

01

NMR spectroscopy

If a compound contains either plane of symmetry or center of symmetry, the protons of the opposite (mirror images) substituents have the same environment. Thus, these protons have given the same signal.

02

Step 2: \(^{\bf{1}}{\bf{H}}\) NMR signals in a, b, and c

a. The given compound has a plane of symmetry as shown below:

Plane of symmetry in a

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

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

Plane of symmetry in b

Thus, the given compound has three types of protons, and it will provide three signals.

c. The given compound has a center of symmetry as shown below:

Center of symmetry in c

Thus, the given compound has three types of protons, and it will provide three signals.

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Most popular questions from this chapter

For each compound give the number of NMR signals, and then determine how many peaks are present for each NMR signal.

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.

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

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?

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?
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