Following are \({ }^{1} \mathrm{H}\)-NMR and \({ }^{13} \mathrm{C} N \mathrm{NMR}\) spectral data for compound \(\mathrm{G}\left(\mathrm{C}_{10} \mathrm{H}_{10} \mathrm{O}\right)\). From this information, deduce the structure of compound \(G\). $$ \begin{array}{lrr} { }^{1} \text { H-NMR } & \multicolumn{2}{c}{{ }^{13} \text { C-NMR }} \\ \hline 2.50(\mathrm{t}, 2 \mathrm{H}) & 210.19 & 126.82 \\ 3.05(\mathrm{t}, 2 \mathrm{H}) & 136.64 & 126.75 \\ 3.58(\mathrm{~s}, 2 \mathrm{H}) & 133.25 & 45.02 \\ 7.1-7.3(\mathrm{~m}, 4 \mathrm{H}) & 128.14 & 38.11 \\ 127.75 & & 28.34 \\ \hline \end{array} $$

Short Answer

Expert verified
Answer: The structure of compound G is para-methoxyethylbenzoate.

Step by step solution

01

Analyzing the given \({ }^{1}\mathrm{H}\)-NMR spectrum

From the given \({ }^{1}\mathrm{H}\)-NMR spectrum, we have four sets of signals: 1. A triplet at 2.50 ppm integrating to 2 H 2. A triplet at 3.05 ppm integrating to 2 H 3. A singlet at 3.58 ppm integrating to 2 H 4. A multiplet between 7.1 and 7.3 ppm integrating to 4 H
02

Analyzing the given \({ }^{13}\mathrm{C}\)-NMR spectrum

From the given \({ }^{13}\mathrm{C}\)-NMR spectrum, we have eight different signals: 1. 210.19 ppm 2. 136.64 ppm 3. 133.25 ppm 4. 128.14 ppm 5. 127.75 ppm 6. 126.82 ppm 7. 126.75 ppm 8. 45.02 ppm 9. 38.11 ppm 10. 28.34 ppm
03

Assigning hydrogen environments

Now, let's assign the environments for the hydrogens using the \({ }^{1}\mathrm{H}\)-NMR spectrum: 1. A triplet at 2.50 ppm integrating to 2 H: This is characteristic for a methylene (-CH2-) group next to an unsaturated system (alkenes, carbonyls). 2. A triplet at 3.05 ppm integrating to 2 H: This is also characteristic for a methylene (-CH2-) group but next to an electronegative atom (oxygen or nitrogen). 3. A singlet at 3.58 ppm integrating to 2 H: A singlet indicates no coupling, indicating these hydrogens are not near another hydrogen. This suggests these hydrogens are attached to an oxygen in a methoxy group (-O-CH3). 4. A multiplet between 7.1 and 7.3 ppm integrating to 4 H: This corresponds to a group of four hydrogens in an aromatic environment.
04

Assigning carbon environments

Using the \({ }^{13}\mathrm{C}\)-NMR spectrum, we can assign the environments for the carbons: 1. 210.19 ppm: Carbonyl carbon (C=O) 2. 136.64 ppm, 133.25 ppm, 128.14 ppm, 127.75 ppm, 126.82 ppm, and 126.75 ppm: These signals are characteristic of aromatic carbons. 3. 45.02 ppm: Methoxy carbon attached to an oxygen (-O-CH3) 4. 38.11 ppm: Methylene (-CH2-) carbon next to a carbonyl group or double bond 5. 28.34 ppm: Methylene (-CH2-) carbon next to an electronegative atom (oxygen or nitrogen)
05

Deduce the structure of compound G

Combining the information obtained from the \({ }^{1}\mathrm{H}\)-NMR and \({ }^{13}\mathrm{C} \mathrm{NMR}\) spectra, we can propose a structure for compound G: 1. The presence of four aromatic hydrogens with six aromatic carbons suggests a disubstituted benzene ring. 2. The presence of a carbonyl group and a methoxy group suggests an ester functional group attached to the benzene ring. 3. Two different methylenes with triplets suggest two ethyl groups with different chemical environments. One ethyl group is attached to the benzene ring, and the other is linked to the carbonyl carbon of the ester. Therefore, the structure of compound G is ethyl benzoate with a methoxy group para to the ester, or para-methoxyethylbenzoate with the molecular formula \(\mathrm{C}_{10}\mathrm{H}_{10}\mathrm{O}\).

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Over 30 million students worldwide already upgrade their learning with Vaia!

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Most popular questions from this chapter

Although most alkanes react with chlorine by a radical chain mechanism when reaction is initiated by light or heat, benzene fails to react under the same conditions. Benzene cannot be converted to chlorobenzene by treatment with chlorine in the presence of light or heat. (a) Explain why benzene fails to react under these conditions. (Consult Appendix 3 for relevant bond dissociation enthalpies.) (b) Explain why the bond dissociation enthalpy of a \(\mathrm{C}-\mathrm{H}\) bond in benzene is significantly greater than that in alkanes.

Draw a structural formula for each compound. (a) 1-Nitronaphthalene (b) 1,6 -Dichloronaphthalene (c) 9-Bromoanthracene (d) 2-Methylphenanthrene

Arrange these compounds in order of increasing acidity: 2,4-dichlorophenol, phenol, cyclohexanol.

Describe the ground-state electron configuration of the cycloheptatrienyl radical and anion. Assuming that each species is planar, would you expect it to be aromatic or antiaromatic?

A finding that opened a route to \(\beta\)-blockers was the discovery that \(\beta\)-blocking activity is retained if an oxygen atom is interposed between the aromatic ring and the side chain. To see this difference, compare the structures of labetalol (Problem 22.55) and propranolol. Thus, alkylation of phenoxide ions can be used as a way to introduce this side chain. The first of this new class of drugs was propranolol. (a) Show how propanolol can be synthesized from 1-naphthol, epichlorohydrin (Section 11.10), and isopropylamine. (b) Is propranolol chiral? If so, which of the possible stereoisomers are formed in this synthesis?

See all solutions

Recommended explanations on Chemistry Textbooks

View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.

Sign-up for free