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Chapter 14: Q.21558-14-8P. (page 537)

For each compound, which of the protons on the highlighted carbons absorbs farther downfield?

a.

b.

c.

Short Answer

Expert verified

a. Blue proton will absorb downfield.

b. Pink proton will absorb downfield.

c. Blue proton will absorb downfield.

Step by step solution

01

Effect of electronegative atom on proton NMR

When an electronegative atom is attached to the CH2 group, the proton near it absorbs downfield.

02

  1H NMR signals in a, b and c

a. F and Cl electronegative atoms are present in the given compound. Cl is less electronegative than F. The CH2 group adjacent to Cl is less deshielded, and its protons absorb upfield.

Thus, the CH2 group adjacent to F absorbs downfield.

b. The CH2 group adjacent to the electronegative oxygen atom absorbs downfield instead of the CH2 group far away from the electronegative atom.

c. The CH2 group adjacent to the electronegative oxygen atom absorbs downfield instead of the CH3 group.

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Most popular questions from this chapter

When 2-bromo-3,3-dimethylbutane is treated with \({{\bf{K}}^{\bf{ + }}}{\bf{ - }}{}^{\bf{ - }}{\bf{OC}}{\left( {{\bf{C}}{{\bf{H}}_{\bf{3}}}} \right)_{\bf{3}}}\), a single product T having molecular formula \({{\bf{C}}_{\bf{6}}}{{\bf{H}}_{{\bf{12}}}}\) is formed. When 3,3-dimethylbutan-2-ol is treated with \({{\bf{H}}_{\bf{2}}}{\bf{S}}{{\bf{O}}_{\bf{4}}}\), the major product U has the same molecular formula. Given the following \({}^{\bf{1}}{\bf{H}}\)-NMR data, what are the structures of T and U? Explain in detail the splitting patterns observed for the three split signals in T. 1 H NMR of T: 1.01 (singlet, 9 H), 4.82 (doublet of doublets, 1 H, J = 10, 1.7 Hz), 4.93 (doublet of doublets, 1 H, J = 18, 1.7 Hz), and 5.83 (doublet of doublets, 1 H, J = 18, 10 Hz) ppm 1 H NMR of U: 1.60 (singlet) ppm.

How many NMR signals does each compound give?

a.

b.

c.

d.

Question: How many \(^{\bf{1}}{\bf{H}}\) NMR signals does each dimethylcyclopropane show?

a.

b.

c.

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

a. A compound X (molecular formula C6H12O2) gives a strong peak in its IR spectrum at 1740 cm-1. The 1 H NMR spectrum of X shows only two singlets, including one at 3.5 ppm. The 13C NMR spectrum is given below Propose a structure for X.

b. A compound Y (molecular formula C6H10 ) gives four lines in its 13C NMR spectrum (27, 30, 67, and 93 ppm), and the IR spectrum given here. Propose a structure for Y.

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

a.

b.

c.
See all solutions

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