Determine the structure of an alcohol with molecular formula C5H12O that exhibits the following signals in its 13C NMR spectra: a. Broadband decoupled: 73.8 δ, 29.1δ, and 9.5 δ b. DEPT-90: 73.8 δ c. DEPT-135: positive signals at 73.8 δ, and 9.5 δ, and negative signal at 29.1δ,

Determine the structure of an alcohol with molecular formula C5H12O that exhibits the following signals in its 13C NMR spectra: a. Broadband decoupled: 73.8 δ, 29.1δ, and 9.5 δ b. DEPT-90: 73.8 δ c. DEPT-135: positive signals at 73.8 δ, and 9.5 δ, and negative signal at 29.1δ,

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter18: Functional Derivatives Of Carboxylic Acids

Section: Chapter Questions

Problem 18.18P: Propose a structural formula for each compound consistent with its 1H-NMR and 13C-NMR spectra. (a)...

See similar textbooks

Related questions

Q: Propose a structure for D (molecular formula C9H9ClO2) consistent with the given spectroscopic data.…

A: Given: The molecular formula of the given compound is C9H9ClO2.

Q: Identify below compound from its spectral data. Molecular formula:C8H8O3 IR:3500–2500 cm−1, 1710…

A: The molecular formula is C8H8O3,. Calculate the double bond equivalence as follows: Double bond…

Q: An unknown compound D exhibits a strong absorption in its IR spectrum at 1692 cm−1. The mass…

A: Given, The absorption of unknown compound is 1692 cm-1. The value of m/z ratio is 150. The base peak…

Q: Propose a structural formula for each compound consistent with its 1H-NMR and 13C-NMR spectra.

Q: Identify the lettered compounds in the following reaction scheme. Compounds F, G, and K are isomers…

Q: Identify the following compound from its IR and proton NMR spectra. C,H1,0: 'H NMR 8 3.31 (3H, s); 8…

A: NMR spectroscopy is a very important tool for the determination of the structure of the organic…

Q: What is the structure of a compound of molecular formula C1H1402 that shows a strong IR absorption…

A: Given that: Molecular formula = C10H14O2 IR absorption = 3150 - 2850 cm-1 H1 NMR absorption =…

Q: - 5. A compound with the molecular formula C,H,O produces a broad signal between 3200 and 3600cm'in…

Q: Compound C has a molecular ion in its mass spectrum at 146 and a prominent absorption in its IR…

A: The IR absorption at 1762 cm-1 suggests the presence of carbonyl ester bond.The molecular ion peak…

Q: Propose a structure for D (molecular formula CgH,CIO,) consistent with the given spectroscopic data.…

A: Nuclear magnetic resonance which is more precisely known as NMR is used to determine the local…

Q: How many signals would the product of the following reaction show in a. its 1H NMR spectrum? b. its…

A: The product formed in the reaction is shown below.

Q: Given here are 1H-NMR and 13C-NMR spectral data for nine compounds. Each compound shows strong…

A: Given: C4H6O2 Splitting in 1H NMR-n+1, n is the number of adjacent protons. Generally, in 1H NMR,…

Q: Given here are 1H-NMR and 13C-NMR spectral data for nine compounds. Each compound shows strong…

A: Given data:

Q: A compound used as a moth repellant has three molecular ion peaks at m/z = 146 (100%), 148 (65%) &…

A: Mass spectrometry is a technique for determining the mass-to-charge ratio (m/z) of one or more…

Q: Propose the structure that corresponds to the following H NMR spectra 1H-NMR, CDCI; Solvent,…

Q: An unknown compound D exhibits a strong absorption in its IR spectrumat 1692 cm−1. The mass spectrum…

Q: An unknown compound D exhibits a strong absorption in its IR spectrum at 1692 cm−1. The mass…

Q: 1. Given the following 'H NMR spectra. А. Draw structure of compound. В. Label peaks (Ha, Hb, He,…

A: The NMR spectrum provides the following details about the structure of the molecules: The number of…

Q: b) A compound with molecular formula C,H1402 upon hydrolysis produces an alcohol and an acid. It has…

Q: Provide a structure for the compound with molecular formula C5H₁00 and with the following…

Q: Propose a structure for each of the following two isomers with formula C6H14 given their 1H-NMR…

Q: An unknown compound produces an 1H NMR spectrum with only three signals: 1.8, 2.8, 7.5 (broad) ppm,…

Q: Identify the lettered compounds in the following reaction scheme. Compounds F, G, and K are isomers…

A: Cyclohexanone reacts with the Grignard reagent to form product A which undergoes dehydration to form…

Q: How can you use 1H NMR spectroscopy to distinguish between CH2 = C(Br)CO2CH3 and methyl…

A: The structures of the given organic compounds, CH2 = C(Br)CO2CH3 and methyl (E)-3-bromopropenoate,…

Q: What is the structure of the compound with the formula C4H10O, if it shows 1H-NMR spectrum: 1.20…

Q: A compound has a molecular formula of C5H3O2 and exhibits the following 13C NMR spectrum. 8 170.67,…

A: Double bond equivalent or the degree of unsaturation of a compound is the number of H2 molecules…

Q: How can the signals in the 6.5 to 8.1 ppm region of their 1H NMR spectra distinguish the following…

A: In NMR spectroscopy, splitting of signal takes place according to number of protons present on…

Q: 12. A compound shows a strong infrared absorption at 1100 cm, but no absorption a 3300 to 3400 cm.…

Q: 1) Propose a structure for the ether of formula C4H100 with the following 1H NMR signals S0.95…

A: The given molecular formula of the compound is C4H10O. It is given that the compound is an ether. It…

Q: Which compound is consistent with the 13C-NMR data shown below? 21.9 (2 x 3H) 41.8 (2H) 31.5 (2H)…

A: Chemical shift: It is the resonance frequency of the nucleus of the carbon atom with respect to the…

Q: How can the signals in the 6.5 to 8.1 ppm region of their 1H NMR spectra distinguish the following…

A: 1H-NMR of 2-methoxynitrobenzne: The structure of 2-methoxynitrobenzné gives four signals in aromatic…

Q: A compound of molecular formula C4H8O2 shows no IR peaks at 3600–3200 or 1700 cm-1. It exhibits one…

A: The given molecular formula of the compound is C4H8O2.The double bond equivalence is calculated by –

Q: The 13C NMR spectrum of 3-pentanone is expected to show signals representing the distinct carbons in…

A: We have to predict the number of signals, carbons,and ppm value.

Q: Identify below compound from its spectral data. Molecular formula:C3H5ClO2 IR:3500–2500 cm−1, 1714…

A: Different types of spectroscopy can be used to identify the structure of unknown compound. Some…

Q: NaOH + Compound C Compound D MW: C12H140 H. H20 'H NMR of Compound D 3H 3H 2H 1H singlet 5H 7 6. 3 2…

A: Aldol condensation: The given reaction is an example of aldol condensatation. The alpha hydrogen of…

Q: Compound X (molecular formula C10H12O) was treated with NH2NH2,−OH to yield compound Y (molecular…

A: The molecular formula of X is C10H12O and the molecular formula of Y is C10H14.

Q: An unknown compound produces an 1H NMR spectrum with only three signals: 1.8, 2.8, 7.5 (broad) ppm,…

A: Determination of molecular mass by mass spectrum: The key point of the mass spectrum and their…

Q: The 1H NMR spectrum of N,N-dimethylformamide shows three singlets at2.9, 3.0, and 8.0 ppm. Explain…

A: The lone pair of electrons on N-atom shifts to the adjacent bonds which results in the double bond…

Q: 1. Given the following 'H NMR spectra. А. Draw structure of compound. В. Label peaks (Ha, Hb, Hg,…

A: Interpretation- Here we have 1H NMR spectra which is given in the question - According to which…

Q: The 'H NMR and 13C spectra of a compound with a molecular formula of C,H1202 are shown below. 1.…

A: The structure of the compound is shown below:

Q: Identify the structures of each compound from the given data.

A: the chemical formula, C6H12O2 indicates that the compound consists six carbon atoms, 12 hydrogen…

Q: Given here are 1H-NMR and 13C-NMR spectral data for nine compounds. Each compound shows strong…

A: The strong IR absorption between 1720 and 1700 cm-1 strongly suggests presence of carboxylic acid…

Q: A compound has a formula of C19H16- Five signals appear in its 1°C NMR spectrum-one at 57 ppm and…

A: Degree of unsaturation It is the number of double bonds or number of rings present in a compound The…

Q: A compound has a molecular formula of C4H602 and exhibits the following 13C NMR spectrum. õ 177.95,…

A: Given:

Q: Question attached

Q: Give structures for the compounds below that show one 1H NMR signal each. C2H6O C4H9Cl c)…

Q: Identify below compound from its spectral data. Molecular formula: C4H7N IR:2250 cm−1 1H NMR…

A: The IR stretching frequency 2250 cm-1 shows that the functional group is -C≡N And from the given 1H…

Q: Given here are 1H-NMR and 13C-NMR spectral data for nine compounds. Each compound shows strong…

A: The structural formula for the compound shows strong absorption between 1720 and 1700 cm-1 and…

Concept explainers

NMR Spectroscopy

NMR stands for Nuclear Magnetic Resonance in which the study of different molecules is done based on the interaction of radiofrequency electromagnetic radiations with the nuclei of molecules placed in a strong magnetic field. A precise study of spectra of visible light and all bands of electromagnetic radiation is called spectroscopy.

Question

Determine the structure of an alcohol with molecular formula C₅H₁₂O that exhibits the following signals in its ¹³C NMR spectra:

a. Broadband decoupled: 73.8 δ, 29.1δ, and 9.5 δ

b. DEPT-90: 73.8 δ

c. DEPT-135: positive signals at 73.8 δ, and 9.5 δ, and negative signal at 29.1δ,

Expert Solution

This question has been solved!

Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.

This is a popular solution!

SEE SOLUTION Check out a sample Q&A here

Step 1

VIEW

Step 2

VIEW

Answer

VIEW

Trending now

This is a popular solution!

Step by step

Solved in 3 steps with 2 images

SEE SOLUTION Check out a sample Q&A here

Knowledge Booster

Learn more about

Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.

Similar questions

Propose a structural formula for each compound consistent with its 1H-NMR and 13C-NMR spectra. (a) C5H10O2 (b) C7H14O2 (c) C6 H12O2 (d) C7H12O4 (e) C4H7ClO2 (f) C4H6O2
Following are 1H-NMR spectra for compounds G, H, and I, each with the molecular formula C5H12O. Each is a liquid at room temperature, is slightly soluble in water, and reacts with sodium metal with the evolution of a gas. (a) Propose structural formulas of compounds G, H, and I. (b) Explain why there are four lines between 0.86 and 0.90 for compound G. (c) Explain why the 2H multiplets at 1.5 and 3.5 for compound H are so complex.
Given the following 13C NMR signals, construct a structure for the unknown compounds. A. Molecular formula: C6H14O DEPT-135 (positive): 14.1 δ DEPT-135 (negative): 22.7 δ, 25.3 δ, 31.8 δ, 32.2 δ, 62.8 δ B. Molecular formula: C7H12O2 Broadband decoupled: 19.1 δ, 28.0 δ, 70.5 δ, 129.0 δ, 129.8 δ, 165.8 δ DEPT-90: 28.0 δ, 129.8 δ DEPT-135 (positive): 19.1 δ, 28.0 δ, 129.8 δ DEPT-135 (negative): 70.5 δ, 129.0 δ
A compound has a formula of C19H16- Five signals appear in its 1°C NMR spectrum-one at 57 ppm and the remaining four between 126 and 144 ppm. In its 'H NMR spectrum, an unresolved multiplet (15 H) appears between 6.9 and 7.44 ppm and a singlet (1 H) appears at 5.5 ppm. What is the structure of this compound?
Assume a compound with the formula C4H8O. a) How many double bonds and/or rings does your compound contain? b) If your compound shows an infrared absorption peak at 1715 cm-1, what functional group does it have? c) If your compound shows a single 1H NMR absorption peak at 2.1 δ, what is its structure?
Given the following 13C NMR signals, construct a structure for the unknown compounds. A. Molecular formula: C4H10O Broadband decoupled: 69.3 δ, 32.1 δ, 22.8 δ, 10.0 δ DEPT-90: 69.3 δ DEPT-135 (positive): 69.3 δ, 22. 8 δ, and 10.0 δ DEPT-135 (negative): 32.1 δ B. Molecular formula: C6H14O DEPT-135 (positive): 14.1 δ DEPT-135 (negative): 22.7 δ, 25.3 δ, 31.8 δ, 32.2 δ, 62.8 δ C. Molecular formula: C7H12O2 Broadband decoupled: 19.1 δ, 28.0 δ, 70.5 δ, 129.0 δ, 129.8 δ, 165.8 δ DEPT-90: 28.0 δ, 129.8 δ DEPT-135 (positive): 19.1 δ, 28.0 δ, 129.8 δ DEPT-135 (negative): 70.5 δ, 129.0 δ
Propose a structure for an alcohol with molecular formula C5H12O that has the 1H NMR spectrum given below. Given chemical shifts and splitting patterns: 0.95 ppm (3H, triplet) 1.3 ppm (6H, singlet) 1.5 ppm (2H, quartet) 2.0 ppm (1H, singlet)
The 1H-NMR spectrum of Compound C shows five signals – δ 2.38 (1H, dt), 2.72 (1H, dt), 5.34 (1H, t), 5.49 (2H, ddd), 6.27 (2H, dd) ppm. Its 13C-NMR spectrum has four signals – δ 26, 58, 127, 129 ppm. In the compound’s mass spectrum, the M+1 peak appears at m/z = 115. An M+2 peak, whose intensity is roughly one-third that of the M+1 peak, also appears. Suggest a structure for this compound.
The structure of an ester could either be A or B: CH3 O O CH3 T || -C-OCH3 CH3-C CH3-C-O-C-CH3 CH3 CH3 A B Its ¹H NMR spectrum consists of two peaks at 80.9 and 83.6 (relative areas 3:1). Which compound is it? Describe the spectrum that would be expected if it had been the other ester.
The 'H NMR spectrum of compound A (C3H100) has four signals: a multiplet at 8 = 7.25-7.32 ppm (5 H), a singlet at d = 5.17 ppm (1 H), a quartet at d = 4.98 ppm (1 H), and a doublet at ô = 1.49 ppm (3 H). There are 6 signals in its 13C NMR spectrum. The IR spectrum has a broad absorption in the -3200 cm-1 region. Compound A reacts with KMNO4 in a basic solution followed by acidification to give compound B with the molecular formula C7H6O2. Draw structures for compounds A and B.
What is the structure of the compound with the formula C8H10O has six signals in its 13C-NMR spectrum. The IR spectrum shows signals at 3400 and 2900 cm-1, the 1H-NMR spectrum is: 1.19 ppm (3H triplet) 2.58 ppm (2H quartet) 4.65 ppm (1H broad singlet) 6.07 ppm (2H doublet) 7.05 ppm (2H doublet)
What is the structure of an unknown compound with molecular formula C6H15N that gives the following 1H NMR absorptions: 0.9 (singlet, 1 H), 1.10 (triplet, 3 H), 1.15 (singlet, 9 H), and 2.6 (quartet, 2 H) ppm?