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Chapter 14: Q.21558-14-6P. (page 535)

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

a.

b.

c.

Short Answer

Expert verified

a. Enantiotopic

b. Neither

c. Diastereotopic

Step by step solution

01

Homotopic, enantiotopic, and diastereotopic protons

• Homotopic protons are formed when the same product is formed by the substitution of two H by Z.

• Enantiotopic protons are formed when two H are equivalent and occur at the same NMR signal.

• Diastereotopic protons are formed when two H are not equivalent and occur at two different signals.

02

Explanation for highlighted proton

a.

The replacement of H with X is shown below.

Enantiotopic proton

b.

The replacement of H with X is shown below.

Neither enantiotopic nor diastereotopic

c.

The replacement of H with X is shown below.

Diastereotopic proton

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Most popular questions from this chapter

Question:Reaction of unknown A with HCl forms chlorohydrin B as the major product. A shows no absorptions in its IR spectrum at 1700 cm-1 or 3600-3200 cm-1 , and gives the following 1H NMR data: 1.4 (doublet, 3 H), 3.0 (quartet of doublets, 1 H), 3.5 (doublet, 1 H), 3.8 (singlet, 3 H), 6.9 (doublet, 2 H), and 7.2 (doublet, 2 H) ppm.

(a) Propose a structure for A, including stereochemistry.

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

Question: The 1 H NMR spectrum of N,N-dimethylformamide shows three singlets at 2.9, 3.0, and 8.0 ppm. Explain why the two groups are not equivalent to each other, thus giving rise to two NMR signals.

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

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Question: Explain why the 13C NMR spectrum of 3-methylbutan-2-ol shows five signals.
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