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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

For each compound, first label each different type of proton and then rank the protons in order of increasing chemical shift.

a.

b.

c.

Question: As we will learn in Chapter 20, reaction of (CH3)2CO withLiC鈮�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鈥�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?

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

Question: Explain why the 13C NMR spectrum of 3-methylbutan-2-ol shows five signals.

Question: Cyclohex-2-enone has two protons on its carbon-carbon double bond (labeled Ha and Hb ) and two protons on the carbon adjacent to the double bond (labeled Hc ). (a) If Jab = 11 Hz and Jbc = 4 Hz, sketch the splitting pattern observed for each proton on the hybridized carbons. (b) Despite the fact that Ha is located adjacent to an electron-withdrawing C=O, its absorption occurs up-field from the signal due to Hb(6.0 vs. 7.0 ppm). Offer an explanation.
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