Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

15. Analytical Techniques:IR, NMR, Mass Spect

Carbon NMR

Organic Chemistry

15. Analytical Techniques:IR, NMR, Mass Spect

Carbon NMR

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4:01 minutes

Problem 69e

Textbook Question

Sketch the following spectra that would be obtained for 2-chloroethanol:
e. The four parts of a DEPT ¹³C NMR spectrum.

Verified step by step guidance

Understand the DEPT 13C NMR technique: DEPT (Distortionless Enhancement by Polarization Transfer) is used to differentiate between CH3, CH2, CH, and quaternary carbons in a molecule. It involves four spectra: DEPT-45, DEPT-90, DEPT-135, and a broadband decoupled spectrum showing all carbons.

Analyze the structure of 2-chloroethanol: The molecule contains two carbons. One is a CH2 group bonded to chlorine, and the other is a CH2 group bonded to hydroxyl (-OH). There are no CH or CH3 groups in this molecule.

Interpret the DEPT spectra: In DEPT-45, all carbons with attached hydrogens (CH, CH2, CH3) appear as positive peaks. In DEPT-90, only CH carbons appear. In DEPT-135, CH and CH3 carbons appear as positive peaks, while CH2 carbons appear as negative peaks. The broadband decoupled spectrum shows all carbons, including quaternary carbons.

Sketch the DEPT spectra for 2-chloroethanol: Since the molecule contains only CH2 carbons, the DEPT-45 spectrum will show two positive peaks, the DEPT-90 spectrum will show no peaks, the DEPT-135 spectrum will show two negative peaks, and the broadband decoupled spectrum will show two positive peaks.

Compare the provided images (A, B, C, D) with the expected DEPT spectra for 2-chloroethanol: Identify the image that matches the description above, where CH2 peaks are positive in DEPT-45, negative in DEPT-135, and present in the broadband decoupled spectrum, while no peaks appear in DEPT-90.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

DEPT NMR Spectroscopy

DEPT (Distortionless Enhancement by Polarization Transfer) NMR is a technique used to differentiate between carbon types in a molecule. It provides information about the number of hydrogen atoms attached to each carbon atom, allowing for the identification of CH3, CH2, and CH groups. This is crucial for interpreting the structure of organic compounds like 2-chloroethanol.

Carbon Types in Organic Molecules

In organic chemistry, carbon atoms can be classified based on their bonding: CH3 (methyl), CH2 (methylene), and CH (methine). Each type has distinct NMR signals, which help in determining the molecular structure. Understanding these types is essential for accurately sketching the DEPT NMR spectrum for compounds such as 2-chloroethanol.

Interpreting NMR Spectra

Interpreting NMR spectra involves analyzing the peaks and their intensities to deduce the molecular structure. In DEPT spectra, the presence or absence of signals for different carbon types indicates how many hydrogen atoms are attached. This skill is vital for accurately sketching the DEPT spectrum for 2-chloroethanol and understanding its chemical environment.

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Related Practice

Textbook Question

Draw the ¹³C NMR spectrum you would expect to see for each of the molecules shown.

(a)

Textbook Question

Draw the ¹³C NMR spectrum you would expect to see for each of the molecules shown.

(b)

Textbook Question

Draw the ¹³C NMR spectrum you would expect to see for each of the molecules shown.

(c)

Textbook Question

How might you use ¹³C NMR spectroscopy to differentiate between the possible ortho, meta, and para products of the electrophilic aromatic substitution reaction shown?

Textbook Question

Identify the compound with molecular formula C₆H₁₀O that gives the following DEPT ¹³C NMR spectrum:

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Textbook Question

The standard ¹³C NMR spectrum of phenyl propanoate is shown here. Predict the appearance of the DEPT-90 and DEPT-135 spectra.

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Textbook Question

Different types of protons and carbons in alkanes tend to absorb at similar chemical shifts, making structure determination difficult. Explain how the ¹³C NMR spectrum, including the DEPT technique, would allow you to distinguish among the following four isomers.

Multiple Choice

How many signals would be expected in the ¹³C NMR spectrum for the following molecule?

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Sketch the following spectra that would be obtained for 2-chloroethanol:e. The four parts of a DEPT 13C NMR spectrum.

Key Concepts

DEPT NMR Spectroscopy

Carbon Types in Organic Molecules

Interpreting NMR Spectra

Watch next

Sketch the following spectra that would be obtained for 2-chloroethanol:
e. The four parts of a DEPT ¹³C NMR spectrum.