Use the figure to answer the question, thanks! How could you distinguish the fol

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Use the figure to answer the question, thanks!

How could you distinguish the following compounds, using their 'H NMR spectra? Drag the terms on the left to the appropriate blanks on the right to complete the sentences. Reset Help The compound A is the only compound without the characteristic benzene ring hydrogens at 7-8 ppm. Only two compounds, A and Bwill have two signals other than the signals for the benzene ring hydrogens. They can be distinguished by integration (2 and 1 in the case of compoundF versus G in the case of compound C),or by the two sharp singlets for the ether versus the somewhat broader singlet for the hydrogen bonded to oxygen. MasteringChemistry: Chapter 18 Homework - Google Chrome Secure https://session.masteringchemistry.com/myctitemView?assignmentProblemID=92819832 Chapter 18 Homework Problem 18.92 2 and 1 Problem 18.92 3 and 2 H2OH 2OH H2OCH3 "OCH3 CH3 Submit My Answers Give Up

Explanation / Answer

compound A is an aliphatic compound so it will not show any signal beyond 5 ppm in proton NMR spectrum unlike other compounds B-G.

compound B and C both will show distinct benzylic proton singlets at nearly 5 ppm ( -OCH2). However, both compounds can be distinguished by the other signal which would appear as broad singlet integrating for 1 proton in case of B (-OH) while a sharp singlet at ~3.5 ppm integrating for 3 protons (OCH3) in case of compound C.

Compound D will show a distinct broad signal highly deshielded between 11-12 ppm characteristic of carboxylic acid proton apart from aromatic proton signals between 7-8 ppm.

compound E can be easily distinguished by characteristic aldehydic proton singlet at 9-10 ppm and aromatic proton signals between 7-8 ppm.

compound F will show a singlet at nearly 3.5-4 ppm integrating for 3 protons from which it can be inferred that CH3 group is attached to an electron withdrawing group like oxygen.

In compound G the singlet appearing at 2-2.5 ppm will integrate for 3 protons suggesting that a methyl group is attached to a carbonyl group.

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