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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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