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Chapter 14: Q19P (page 636)

One of the spectra below is produced by 1-chloropropane and the other by 1-iodopropane. Which is which?

Short Answer

Expert verified

The signal in the range 3.3- 3.1 ppm shows the spectra produced by 1-iodopropane.

The signal in the range 3.6-3.4 ppm shows the spectra produced by 1-chloropropane.

Step by step solution

01

Step-by-Step SolutionStep 1: Electronegativity of heteroatoms

The electronegativity of an atom shifts the signal downfield.The electronegativity of chlorine is high. Therefore, the signal of 1-chloropropane is downfield than 1-iodopropane.

02

Position of electronegativity atoms

The electronegative atom is closely attached to the proton, and its chemical shift is more downfield than others.

Hence, the signal in the range 3.3- 3.1 ppm shows the spectra produced by 1-iodopropane.

The signal in the range 3.6-3.4 ppm shows the spectra produced by 1-chloropropane.

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Most popular questions from this chapter

Identify each of the following compounds from its molecular formula and its 13C NMR spectrum:

a.C4H10O

b.C6H12O

Identify each of the following compounds from its molecular formula and its IR and 1H NMR spectra:

a. C6H120

b.C6H14O

c. C10H13NO3

d. C11H14O2

Identify the compound with a molecular formula C8H10O that gives the IR and H1NMR spectra shown here.

Which underlined proton (or sets of protons) has the greater chemical shift (that is, the higher frequency signal)?

Why is there no coupling between the a and c protons or between the b and c protons in the cis and trans alkenes shown in Figure 14.20?
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