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Without referring to Table 15.1, label the proton or set

Chapter 15, Problem 14P

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QUESTION:

Without referring to Table \(15.1\) , label the proton or set of protons in each compound that gives

the signal at the lowest frequency a, at the next lowest b, and so on.

Equation Transcription:

Text Transcription:

15.1

Questions & Answers

QUESTION:

Without referring to Table \(15.1\) , label the proton or set of protons in each compound that gives

the signal at the lowest frequency a, at the next lowest b, and so on.

Equation Transcription:

Text Transcription:

15.1

ANSWER:

Solution 14P

(a)

The magnetic fields induced by the electrons of a carbonyl group in the aldehydic protons have the same direction as the applied magnetic field. Since a larger effective magnetic field is sensed by the proton, it shows chemical shift at higher frequency.

Carbon is more electronegative than hydrogen. So, the chemical shift of a methine proton is more deshielded and, thus, shows a chemical shift at a higher frequency than the chemical shift of methylene protons.

Therefore, set of protons in propanal that give the signal at the lowest frequency a, the next lowest b, and so on is as follows:

(b)

The chemical shift value increases with increasing electronegativity of atom.

Carbon is more electronegative than hydrogen. So, the chemical shift of a methine proton is more deshielded and, thus, shows a chemical shift at a higher frequency than the chemical shift of methylene protons.

Therefore, set of protons in 3-methoxypentane that gives the signal at the lowest frequency a, the next lowest b, and so on is as follows:

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