1. This question refers to the product of this reaction: methyl salicylate. a. Classify the two substituents (the ester group and the hydroxyl group) as either electron- donating or electron-withdrawing groups and draw resonance structures to illustrate the effect. Ester group: (d) H (e) H H (c) CH3(b) HO Hydroxyl group: (a) H (c) CH3(b) (d) H H (a) (e) H HO b. Based on the resonance structures, which of the aromatic protons are more shielded and which are less shielded? Which of these protons will be at located at a larger chemical shift and which will be at a smaller chemical shift? Explain briefly.

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Chapter1: Chemical Foundations
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Please answer the following pertaining to organic chemistry

1. This question refers to the product of this reaction: methyl salicylate.
a. Classify the two substituents (the ester group and the hydroxyl group) as either electron-
donating or electron-withdrawing groups and draw resonance structures to illustrate the effect.
Ester group:
(d) H
H (c)
(e) H
H
(a)
Hydroxyl group:
CH3 (b)
(d) H
H (c)
CH3(b)
(e) H
H
(a)
b.
Based on the resonance structures, which of the aromatic protons are more shielded and
which are less shielded? Which of these protons will be at located at a larger chemical shift
and which will be at a smaller chemical shift? Explain briefly.
Transcribed Image Text:1. This question refers to the product of this reaction: methyl salicylate. a. Classify the two substituents (the ester group and the hydroxyl group) as either electron- donating or electron-withdrawing groups and draw resonance structures to illustrate the effect. Ester group: (d) H H (c) (e) H H (a) Hydroxyl group: CH3 (b) (d) H H (c) CH3(b) (e) H H (a) b. Based on the resonance structures, which of the aromatic protons are more shielded and which are less shielded? Which of these protons will be at located at a larger chemical shift and which will be at a smaller chemical shift? Explain briefly.
C.
Predict the multiplicity of each of the aromatic protons and briefly explain your predictions.
i.
H (c)
ii.
H (d)
iv.
H (e)
H (f)
Transcribed Image Text:C. Predict the multiplicity of each of the aromatic protons and briefly explain your predictions. i. H (c) ii. H (d) iv. H (e) H (f)
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