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Chapter 14: Q.21558-14-48P (page 563)

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

Short Answer

Expert verified

Answer

a. Five

b. Three

c. Seven

d. Three

e. Seven

f. Five

g. Four

h. Three

Step by step solution

01

Step 1:  13C NMR spectroscopy

13C Spectroscopy gives the high value of chemical shift signal when the carbon-13 is present in the vicinity of the electron-withdrawing groups.

13C 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 13C spectroscopy are represented as:

a.

It has five signals due to the presence of five different 13C .

13C signal

b.

It has three signals due to the presence of three different 13C .

13C signal

c.

It has seven signals due to the presence of seven different 13C .

13C signal

d.

It has three signals due to the presence of three different 13C .

13C signal

e.

It has seven signals due to the presence of seven different 13C .

13C signal

f.

It has five signals due to the presence of five different 13C .

13C signal

g.

It has four signals due to the presence of four different 13C .

13C signal

h.

It has three signals due to the presence of three different 13C

13C signal

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Most popular questions from this chapter

Question: a. How many signals does dimethyl fumarate ( CH3O2CCH=CHC02CH3 with a trans C=C) exhibit in its 13C NMR spectrum? b. Draw the structure of an isomer of dimethyl fumarate that has each of the following number of signals in its 13C NMR spectrum: [1] three; [2] four; [5] five

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

a.

b.

c.

Question:Propose a structure consistent with each set of spectral data:

a. C4H8Br2: IR peak at 3000โ€“2850cm-1 ;

NMR (ppm):

1.87 (singlet, 6 H)

3.86 (singlet, 2 H)

b. C3H6Br2: IR peak at 3000โ€“2850cm-1 ;

NMR (ppm):

2.4 (quintet)

3.5 (triplet)

c. C5H10O2: IR peak at 1740cm-1 ;

NMR (ppm):

1.15 (triplet, 3 H) 2.30 (quartet, 2 H)

1.25 (triplet, 3 H) 4.72 (quartet, 2 H)

d . C6H14O: IR peak at 3600-3200 cm-1 ;

NMR (ppm):

0.8 (triplet, 6 H) 1.5 (quartet, 4 H)

1.0 (singlet, 3 H) 1.6 (singlet, 1 H)

e. C6H14O: IR peak at 3000-2850cm-1 ;

NMR (ppm):

1.10 (doublet, relative area = 6)

3.60 (septet, relative area = 1)

f . C3H6O: IR peak at 1730cm-1 ;

NMR (ppm):

1.11 (triplet)

2.46 (multiplet)

9.79 (triplet)

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

Label each statement as True or False.

a. When a nucleus is strongly shielded, the effective field is larger than the applied field and the absorption shifts downfield.

b. When a nucleus is strongly shielded, the effective field is smaller than the applied field and the absorption is shifted upfield.

c. A nucleus that is strongly deshielded requires a lower field strength for resonance.

d. A nucleus that is strongly shielded absorbs at a larger ฮด value.

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