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Chapter 14: Q7P (page 527)

Question: How many \(^{\bf{1}}{\bf{H}}\) NMR signals would you expect for each compound?

a.

b.

c.

Short Answer

Expert verified
  1. 4
  2. 5
  3. 5

Step by step solution

01

NMR spectroscopy

The chemical shift of a proton is affected by the presence of an electronegative atom. The proton around the electronegative atom is deshielded, due to which it absorbs downfield.

02

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

a.

The given compound has four types of protons, and it will give four signals, as shown below.

Structure of a

b.

The given compound has five types of protons, and it will give five signals, as shown below.

Structure of b

c.

The given compound has five types of protons, and it will give five signals, as shown below.

Structure of c

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Most popular questions from this chapter

For each compound, first label each different type of proton and then rank the protons in order of increasing chemical shift.

a.

b.

c.

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.

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

Question: Explain why the carbonyl carbon of an aldehyde or ketone absorbs farther downfield than the carbonyl carbon of an ester in a 13C NMR spectrum

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.

(b) Explain why B is the major product in this reaction.
See all solutions

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