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Chapter 14: Q48P (page 527)

How many \(^{{\bf{13}}}{\bf{C}}\) NMR signals do each compound exhibit?

a.

b.

c.

d.

e.

f.

g.

h.

Short Answer

Expert verified

a. Five

b. Three

c. Seven

d. Three

e. Seven

f. Five

g. Four

h. Three

Step by step solution

01

Step 1: \(^{{\bf{13}}}{\bf{C}}\) NMR spectroscopy

\(^{{\bf{13}}}{\bf{C}}\)Spectroscopy gives the high value of chemical shift signal when the carbon-13 is present in the vicinity of the electron-withdrawing groups.

\(^{{\bf{13}}}{\bf{C}}\)Spectroscopy gives the low value of chemical shift signal when the carbon-13 is present in the vicinity of the electron-rich groups.

02

Explanation

The different signals of\(^{{\rm{13}}}{\rm{C}}\)spectroscopy are represented as:

a.

It has five signals due to the presence of five different \(^{{\rm{13}}}{\rm{C}}\).

b.

It has three signals due to the presence of three different\(^{{\rm{13}}}{\rm{C}}\).

c.

It has seven signals due to the presence of seven different\(^{{\rm{13}}}{\rm{C}}\).

d.

It has three signals due to the presence of three different \(^{{\rm{13}}}{\rm{C}}\).

e.

It has seven signals due to the presence of seven different \(^{{\rm{13}}}{\rm{C}}\).

f.

It has five signals due to the presence of five different \(^{{\rm{13}}}{\rm{C}}\).

g. It has four signals due to the presence of four different \(^{{\rm{13}}}{\rm{C}}\).

h.

It has three signals due to the presence of three different \(^{{\rm{13}}}{\rm{C}}\).

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Most popular questions from this chapter

The reaction of (CH3)3 CCHO with (C6H5)3 P=C(CH3)OCH3 , followed by treatment with aqueous acid, afford R . R has strong absorption in its IR spectrum at 1717 cm-1 and three singlets in its -NMR spectrum at 1.02 (9 H), 2.13 (3 H), and 2.33 (2 H) ppm. What is the structure of R? We will learn about this reaction in Chapter 21.

Question: As we will learn in Chapter 20, reaction of (CH3)2CO withLiC≡CH followed by affords compound D, which has a molecular ion in its mass spectrum at 84 and prominent absorptions in its IR spectrum at 3600–3200, 3303, 2938, and 2120cm-1 . D shows the following 1 H NMR spectral data: 1.53 (singlet, 6 H), 2.37 (singlet, 1 H), and 2.43 (singlet, 1 H) ppm. What is the structure of D?

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.

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 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

b. \){\left( {{\bf{C}}{{\bf{H}}_{\bf{3}}}} \right)_{\bf{2}}}{\bf{CHCHO}}\); \)^{{\bf{13}}}{\bf{C}}\) NMR: 16, 41, and 205 ppm

c. \){\bf{C}}{{\bf{H}}_{\bf{2}}}{\bf{ = CHCH}}\left( {{\bf{OH}}} \right){\bf{C}}{{\bf{H}}_{\bf{3}}}\); \)^{{\bf{13}}}{\bf{C}}\) NMR: 23, 69, 113, and 143 ppm
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