Draw the expected signal for a hydrogen with the following coupling constants.

(a) Hₐ : δ 5.34 (Jₐ꜀ = 12 , Jₐ₆ = 2)

Draw the expected signal for a hydrogen with the following coupling constants.

(b) Hₐ : δ 3.34 (Jₐ꜀ = 9 , Jₐ₆ = 4 )

Though it wasn't discussed, what coupling constant would you expect for Hₐ and H꜀ in the spectrum of trans-but-2-enoic acid in Figure 15.50? Justify your answer.

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Replace Hₐ and H₆ in hexane with a deuterium. What is the relationship between the two products you obtain? Based on this, would you expect the two hydrogens to give one or two signals in the ¹H NMR spectrum?

Replace Hₐ, H₆, and H꜀ in methyl benzene with a deuterium. What is the relationship between the three products you obtain? Based on this, how many signals would you expect for these hydrogens in the ¹H NMR spectrum?

Replace Hₐ and H₆ in acetone with a deuterium. What is the relationship between the two products you obtain? Based on this, would you expect the two hydrogens to give one or two signals in the ¹H NMR spectrum?

Sketch the signals you would expect to see for Hₐ in the molecule shown. The important coupling constants are given.

Sketch the signals you would expect to see for H_b in the molecule shown. The important coupling constants are given.

Sketch the signals you would expect to see for H꜀ in the molecule shown. The important coupling constants are given.

How many signals would you expect in the ¹³C NMR spectrum of each molecule shown?

(b)

How many signals would you expect in the ¹³C NMR spectrum of each molecule shown?

(c)

Draw the ¹³C NMR spectrum of each molecule in Assessment 15.48.

(a)

Draw the ¹³C NMR spectrum of each molecule in Assessment 15.48.

(b)

Draw the ¹³C NMR spectrum of each molecule in Assessment 15.48.

(c)

Assign each signal in the ¹³C NMR spectra to the molecule shown.

(a) <IMAGE>

Assign each signal in the ¹³C NMR spectra to the molecule shown.

(b) <IMAGE>

Draw the expected results of a DEPT sequence for the molecules shown.

(a)

Draw the expected results of a DEPT sequence for the molecules shown.

(b)

With information from the ¹H NMR and the ¹³C DEPT spectra, structure elucidation becomes even easier. Provide the structure that corresponds to the following data. [The identity of the carbons comes from the DEPT experiment.]

C₆H₁₁BrO₂

IR: 1745 cm ⁻¹

¹H NMR: δ 1.25 (t, 3H), 2.18 (quint, 2H), 2.58 (t, 2H), 3.46 (t, 2H), 4.15 (q, 2H)

¹³C NMR: δ 14.2 (CH₃) , 27.8 (CH₂) , 32.5 (CH₂) , 32.6 (CH₂) , 60.5 (CH₂) , 172.4 (C)

How many distinct signals would you expect to see in the ¹H NMR spectrum of the following molecules? [Ignore diastereotopic hydrogens for the sake of this assessment.]

(a)

How many distinct signals would you expect to see in the ¹H NMR spectrum of the following molecules? [Ignore diastereotopic hydrogens for the sake of this assessment.]

(b)

How many distinct signals would you expect to see in the ¹H NMR spectrum of the following molecules? [Ignore diastereotopic hydrogens for the sake of this assessment.]

(c)

How many distinct signals would you expect to see in the ¹H NMR spectrum of the following molecules? [Ignore diastereotopic hydrogens for the sake of this assessment.]

(f)

For the following molecules, give the integration you would expect for the signal associated with the hydrogens at the labeled carbons. [Pay attention to the symmetry, or lack of symmetry, in the molecules.]

(c)

For the following molecules, give the integration you would expect for the signal associated with the hydrogens at the labeled carbons. [Pay attention to the symmetry, or lack of symmetry, in the molecules.]

(e)

For the following molecules, give the integration you would expect for the signal associated with the hydrogens at the labeled carbons. [Pay attention to the symmetry, or lack of symmetry, in the molecules.]

(f)

For the following molecules, give the chemical shift for each indicated hydrogen.

(b)

For the following molecules, give the chemical shift for each indicated hydrogen.

(d)

For the following molecules, give the chemical shift for each indicated hydrogen.

(e)

Predict the splitting pattern for each of the indicated hydrogens in Assessment 15.59.

(a)