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

Structure Determination without Mass Spect

Organic Chemistry

15. Analytical Techniques:IR, NMR, Mass Spect

Structure Determination without Mass Spect

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6:30 minutes

Problem 77b

Textbook Question

Identify each of the following compounds from its molecular formula and its IR and ¹H NMR spectra:
b.C₆H₁₄O
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Verified step by step guidance

Step 1: Analyze the molecular formula (C6H14O). The formula indicates the compound contains 6 carbons, 14 hydrogens, and 1 oxygen. Calculate the degree of unsaturation using the formula: \( ext{Degree of Unsaturation} = rac{2C + 2 - H + N - X}{2} \), where \( C \) is the number of carbons, \( H \) is the number of hydrogens, \( N \) is the number of nitrogens, and \( X \) is the number of halogens. For C6H14O, the degree of unsaturation is 0, meaning the compound is fully saturated (no double bonds, triple bonds, or rings).

Step 2: Examine the IR spectrum. Look for characteristic absorption bands that indicate the presence of functional groups. For example, a broad peak around 3200-3600 cm⁻¹ suggests the presence of an -OH group (alcohol). If no such peak is observed, the oxygen might be part of an ether group.

Step 3: Analyze the 1H NMR spectrum. Look for the number of signals, their chemical shifts, splitting patterns, and integration values. For example, a signal around 3.3-4.0 ppm could indicate protons adjacent to an oxygen atom (e.g., in an alcohol or ether). The splitting patterns (singlet, doublet, triplet, etc.) provide information about the number of neighboring hydrogens, and the integration values indicate the relative number of hydrogens contributing to each signal.

Step 4: Combine the information from the IR and 1H NMR spectra. If the IR spectrum shows an -OH group and the NMR spectrum has a singlet corresponding to a hydroxyl proton (around 1-5 ppm), the compound is likely an alcohol. If the IR spectrum lacks an -OH peak and the NMR spectrum shows signals consistent with an ether, the compound is likely an ether.

Step 5: Propose a structure for the compound based on the molecular formula, degree of unsaturation, and spectral data. For example, if the IR spectrum shows an -OH group and the NMR spectrum indicates a simple alcohol structure, the compound could be a hexanol isomer. If the IR spectrum suggests an ether and the NMR spectrum supports this, the compound could be a hexyl ether isomer. Verify the proposed structure by ensuring it matches all spectral data.

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Key Concepts

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

Molecular Formula Interpretation

The molecular formula provides essential information about the number and types of atoms in a compound. For C6H14O, it indicates the presence of six carbon atoms, fourteen hydrogen atoms, and one oxygen atom. Understanding how to interpret this formula helps in predicting the possible structures and functional groups present in the compound.

Infrared (IR) Spectroscopy

IR spectroscopy is a technique used to identify functional groups in a molecule based on the absorption of infrared light. Different bonds absorb characteristic wavelengths, allowing for the identification of functional groups such as alcohols, ethers, and alkanes. Analyzing the IR spectrum of C6H14O will reveal specific peaks that correspond to the O-H stretch of alcohols, aiding in compound identification.

Proton Nuclear Magnetic Resonance (1H NMR) Spectroscopy

1H NMR spectroscopy provides information about the hydrogen atoms in a molecule, including their environment and connectivity. The chemical shifts, splitting patterns, and integration of peaks in the NMR spectrum can reveal the number of hydrogen atoms in different environments, helping to deduce the structure of C6H14O. This technique is crucial for confirming the identity of the compound based on its unique spectral characteristics.

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Related Practice

Textbook Question

Shown below is the ¹H NMR spectrum of the alkyl bromide used to make the phosphonium ylide that reacts with a ketone in a Wittig reaction to form a compound with molecular formula C₁₁H₁₄. What product is obtained from the Wittig reaction?

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Textbook Question

An aromatic hydrocarbon with a molecular formula of C₁₃H₂₀ has an ¹H NMR spectrum with a signal at ~7 ppm that integrates to 5H. It also has two singlets; one of the singlets has 1.5 times the area of the second. What is the structure of the aromatic hydrocarbon?

Textbook Question

The proton and ¹³C NMR spectra of a compound of formula C₄H₁₁N are shown here. Determine the structure of this amine, and give peak assignments for all of the protons in the structure.

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Textbook Question

Identify each of the following compounds from its molecular formula and its IR and ¹H NMR spectra:

b. C₆H₁₂O₂

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Textbook Question

A compound with molecular formula C₅H₁₀O₂ gives the following IR spectrum. When it undergoes acid-catalyzed hydrolysis, the compound with the ¹H NMR spectrum shown below is formed. Identify the compounds.

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Textbook Question

An unknown compound (C₃H₂NCl) shows moderately strong IR absorptions around 1650 cm^–1 and 2200 cm^–1. Its NMR spectrum consists of two doublets (J = 14 Hz) at δ5.9 and δ7.1. Propose a structure consistent with these data.

Textbook Question

Identify each of the following compounds from its molecular formula and its IR and ¹H NMR spectra.

d. C₄H₈O₂

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Open Question

Propose a structure for the following compound that fits the following 1H NMR data:

Formula:C₃H₈O₂ ¹H NMR:3.36 δ (6H, singlet)

4.57 δ (2H, singlet)

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Identify each of the following compounds from its molecular formula and its IR and 1H NMR spectra: b.C6H14O<IMAGE>

Key Concepts

Molecular Formula Interpretation

Infrared (IR) Spectroscopy

Proton Nuclear Magnetic Resonance (1H NMR) Spectroscopy

Watch next

Identify each of the following compounds from its molecular formula and its IR and ¹H NMR spectra:
b.C₆H₁₄O
<IMAGE>