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Chapter 14: Q.21558-14-7P. (page 535)

How many NMR signals would you expect for each compound?

a.

b.

c.

Short Answer

Expert verified

a. 4

b. 5

c. 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

 1H 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

Identify A and B, isomers of molecular formula C3H4Cl2 , from the given 1HNMR data: Compound A exhibits signals at 1.75 (doublet, 3H,J = 6.9 Hz) and 5.89 (quartet, 1H, J = 6.9 Hz) ppm. Compound B exhibits signals at 4.16 (singlet, 2 H), 5.42 (doublet, 1H, J = 1.9 Hz), and 5.59 (doublet, 1H, J = 1.9 Hz) ppm.

Question: Rank the highlighted carbon atoms in each compound in order of increasing chemical shift.

a.

b.

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

How many peaks are observed in the 1HNMR signal for each proton shown in red in palau'amine, the complex chapter-opening molecule?

Question: Compound C has a molecular ion in its mass spectrum at 146 and a prominent absorption in its IR spectrum at 1762cm-1 . C shows the following 1H NMR spectral data: 1.47 (doublet, 3 H), 2.07 (singlet, 6 H), and 6.84 (quartet, 1 H) ppm. What is the structure of C?
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