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Chapter 14: Q51P (page 527)

a. How many signals does dimethyl fumarate (\({\bf{C}}{{\bf{H}}_{\bf{3}}}{{\bf{O}}_{\bf{2}}}{\bf{CCH = CHC}}{{\bf{O}}_{\bf{2}}}{\bf{C}}{{\bf{H}}_{\bf{3}}}\) with a trans C=C) exhibit in its \(^{{\bf{13}}}{\bf{C}}\) NMR spectrum?

b. Draw the structure of an isomer of dimethyl fumarate that has each of the following number of signals in its \(^{{\bf{13}}}{\bf{C}}\) NMR spectrum:\(\left( {\bf{1}} \right)\) three; \(\left( {\bf{2}} \right)\) four; \(\left( {\bf{5}} \right)\) five

Short Answer

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a.

b.

Step by step solution

01

Dimethyl fumarate

\(^{{\bf{13}}}{\bf{C}}\)The dimethyl fumarate has two\({\bf{C}}{{\bf{H}}_{\bf{3}}}{\bf{C}}{{\bf{O}}_{\bf{2}}}\)group which are arranged in different orientations. Therefore, the dimethyl fumarate total has 4 isomers.

02

Step 2: \(^{{\bf{13}}}{\bf{C}}\) signals

Dimethyl fumarate has different types of orientation of groups. For example, the trans orientation of groups give 3 signals in the \(^{{\rm{13}}}{\rm{C}}\) spectroscopy while in the geminal orientation of groups, the number of signals is 4.

03

Explanation

a.

The trans dimethyl fumarate has three signals in \(^{{\rm{13}}}{\rm{C}}\) spectroscopy as shown below:

b.

The isomers of dimethyl fumarate with signals are shown below:

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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: Label the protons in each highlighted \({\bf{C}}{{\bf{H}}_{\bf{2}}}\) group as enantiotopic, diastereotopic, or homotopic.

a.

b.

c.

Question. Reaction of aldehyde D with amino alcohol E in the presence of NaH forms F (molecular formula C11H15NO2). F absorbs at 1730 cm-1in its IR spectrum. F also shows eight lines in its 13C-NMR spectrum, and gives the following -NMR spectrum: 2.32 (singlet, 6 H), 3.05 (triplet, 2 H), 4.20 (triplet, 2 H), 6.97 (doublet, 2 H), 7.82 (doublet, 2 H), and 9.97 (singlet, 1 H) ppm. Propose a structure for F. We will learn about this reaction in Chapter 18.

Question: What splitting pattern is observed for each proton in the following compounds?

a.

b.

Question: A compound of molecular formula C4H802 shows no IR peaks at 3600–3200 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?
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