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Draw the NMR spectra you would expect for the following

Chapter 18, Problem 7P

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QUESTION:

Draw the NMR spectra you would expect for the following compounds.

(a) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}-\mathrm{O}-\mathrm{CH}\left(\mathrm{CH}_{3}\right)_{2}\)

(c) \(\mathrm{Ph}-\mathrm{CH}\left(\mathrm{CH}_{3}\right)_{2}\)

Equation Transcription:

Text Transcription:

(CH_{3})_{2}CH-O-CH(CH_{3})_{2}

Cl-CH_{2}-CH_{2}-C-O-CH_{3}

Ph-CH(CH_{3})_{2}

CH_{3}CH_{2}O

OCH_{2}CH_{3}

CH_{2}-COOCH_{2}CH_{3}

CH_{2}-COOCH_{2}CH_{3}

Questions & Answers

QUESTION:

Draw the NMR spectra you would expect for the following compounds.

(a) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}-\mathrm{O}-\mathrm{CH}\left(\mathrm{CH}_{3}\right)_{2}\)

(c) \(\mathrm{Ph}-\mathrm{CH}\left(\mathrm{CH}_{3}\right)_{2}\)

Equation Transcription:

Text Transcription:

(CH_{3})_{2}CH-O-CH(CH_{3})_{2}

Cl-CH_{2}-CH_{2}-C-O-CH_{3}

Ph-CH(CH_{3})_{2}

CH_{3}CH_{2}O

OCH_{2}CH_{3}

CH_{2}-COOCH_{2}CH_{3}

CH_{2}-COOCH_{2}CH_{3}

ANSWER:

Solution 7P

(a)

In 2-isopropoxypropane, two types of protons are present. They are “a” set of protons and “b” set of protons. Here, four methyl groups (“a” set of protons) give doublet at 1.13 because these groups are adjacent to methine group. Two methyne groups (“b” set of protons) give multiplet at 3.19 because these groups are adjacent to more electronegative atom, oxygen.

Thus, the 1H NMR spectrum of 2-isopropoxypropane is as follows:

(b)

In methyl 3-chloropropanoate, three types of protons are present. They are “a” set of protons, “b” set of protons, and “c” set of protons. Here, methyl group (“b” set of protons) gives singlet at 3.68 because this group is adjacent to oxygen. Methylene group (“a” set of protons) gives triplet at 2.53 because this group is adjacent to carbonyl group. Methylene group (“c” set of protons) gives triplet at 3.90 because this group is adjacent to more electronegative atom, chlorine.

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