One of the spectra in the figure below is produced 1-chloropropane and the other

Question

One of the spectra in the figure below is produced 1-chloropropane and the other by 1-iodopropane. Which is which? Check aII that apply. The first spectrum is the^1H NMR spectrum for 1-chloropropane. The second spectrum is the^1H NMR spectrum for 1-chloropropane. The first spectrum is the^1H NMR spectrum for 1-iodopropane. The second spectrum is the^1H NMR spectrum for 1-iodopropane. Which set of protons in each compound is the most shielded? How the following compounds, each with the same molecular formula, could be distinguished by their^1 H NMR spectra? Check all that apply. A has two signals. B has two signals. C has two signals. A has three signals triplet, multiplet, multiplet. B has three signals; triplet, triplet, doublet C has three signals; doublet, triplet, multiplet A has three signals; triplet, triplet, multiplet. B has three signals; doublet, multiplet, doublet The^1H NMR spectrum of a compound with the formula C_4HsCl_2 consists of a triplet at delta 3.6 ppm and a triplet at 1.9 ppm in the ratio of 1:1. What compound is consistent with this spectrum

Explanation / Answer

Part A) Cl is more electronegative than I. So the CH2 protons would be more downfield when attached to Cl in 1-chloropropane as compared to CH2 protons of 1-iodopropane.

Thus, the first (top) spectrum is for 1-iodopropane

the bottom (second) spectrum is for 1-chlorpropane

Part B) Most shielded proton in each compound would be,

1. 1

2. 4

3. 7

Part C) the three compounds in 1H NMR would show,

C has two signals

A has three signals triplet, triplet and a multiplet

B has three signals doublet, multiplet and doublet

Part D) The compound would have a structure,

Cl-CH2-CH2-CH2-CH2-Cl

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