Answered: Propose a structure consistent with…

Propose a structure consistent with following set of spectral data: C5H10O2: IR peak at 1740 cm−1; NMR (ppm): 1.15 (triplet, 3 H) 2.30 (quartet, 2 H) 1.25 (triplet, 3 H) 4.72 (quartet, 2 H)

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

Chapter21: Benzene And The Concept Of Aromaticity

Section: Chapter Questions

Problem 21.20P

See similar textbooks

Related questions

Q: Which of the following compounds are aromatic and anti-aromatic? Give justifications for your…

A: The species given are,

Q: 1. A) What type of shift has occurred to anthracene when compared to benzene? Explain your answer.…

A: Bathochromic shift (red shift): a shift to lower energy or longer wavelength. • Hypsochromic…

Q: The spectrum of compound F with molecular formula C5H602 is shown below. IR spectrum shows a medium…

Q: Propose a structure that is consistent with following spectral data given by a compound with the…

Q: Draw a structure consistent with the following set of data: a hydrocarbon with a molecular ion at…

Q: Propose possible structures consistent with each set of data. Assume each compound has an sp…

A: a) The molecular ion at m/z=72 C=MM13=7213=5713H=quotient +remainder=5+7=12 The base formula is…

Q: Treatment of benzaldehyde (CgH,CHO) with Zn(Hg) in aqueous HCI forms a compound Z that has a…

A: Given: Molecular ion of a compound Z = 92 IR spectra = 3150-2950 cm-1, 1605 and 1496 cm-1 From the…

Q: Oxidation of citronellol, a constituent of rose and geranium oils, with PCC in the presence of added…

A: a) Oxidation of citronellol with PCC in the presence of added NaOCOCH3 forms a compound A. The…

Q: There is a Compound called A with the formula C13H20N2O2. In the proton NMR two triplets at 2.8 and…

A: The amino group at para position on benzene ring to ester carbonyl increases electron density on…

Q: Propose a structure for a compound of molecular formula C3H8O with an IR absorption at 3600–3200…

Q: 69 1000- 800.0 600.0 41 400.0 128 100 123 200.0 151 196 0.000 50.00 100.0 150.0 200.0 m/z Abundance

A: There are two common types of NMR: 1H NMR and 13C NMR. The main difference between 1H NMR and 13C…

Q: A compound shows strong, very broad IR absorption in the region 3300–3600 cm-1 and strong, sharp…

A: Infrared spectroscopy (IR) involves the measurement of vibrations by the interaction of infrared…

Q: :) Propose a structure for compound A that satisfies ALL the data provided: (GIVE REASONS FOR YOUR…

A: Note : MF = C5H10 (DBE= 5-10/2+1 = 6-5 = 1). Compound A do not decolorizes the bromine solution…

Q: Reaction of pentanoyl chloride (CH3CH2CH¿CH¿COCI) with lithium dimethyl cuprate [LiCu(CHa] forms a…

A: MASS SPECTRUM: Mass spectrum is used to analyze chemical compounds with the help of mass to charge…

Q: Calculate the index of hydrogen deficiency (degrees of unsaturation) for the following molecule with…

A: The structure of the following is:

Q: The mass spectrum of compound A shows the molecular lon at miz 85, an M+1 peak at m/z 86 of…

A: Mass spectrometry is an important tool for the determination of the molecular mass of the compound…

Q: 1. Propose a structure for a compound that meet the following criteria: a. CSH3, with IR absorptions…

A: Applying stretching frequency values of functional groups in IR spectroscopy.

Q: A chiral hydrocarbon X exhibits a molecular ion at 82 in its mass spectrum. The IR spectrum of X…

Q: Propose a structure consistent with each set of data.a.) C9H10O2: IR absorption at 1718 cm−1 b.)…

A: (a) The DBU calculation for C9H10O2 is as follows: DBU = 9 - 10/2 + 1 = 5 This suggests the presence…

Q: Propose a structure for a compound of molecular formula C3H8O with an IR absorption at 3600–3200…

A: Calculation of double bond equivalence: DBE = C +1 – (H + X – N) / 2 Here, C is the number of carbon…

Q: Compound K: molecular ion at 88; IR peak at 3600-3200 cm-1; 1H NMR data (ppm) at 0.9 (triplet, 3H),…

Q: A chemist is summoned to an abandoned waste-disposal site to determine the contents of a leaking,…

A: (a)

Q: C6H15N

Q: Compound X of the molecular formula C7H10 has the 13C NMR spectrum (5 signals) shown below. On…

A: DBE = 7- (10/2)+1 = 8-5 = 3. Therefore the compound is having one ring and two double bonds.…

Q: What is the element of unsaturation of the molecular formula? Show the math you use: 2. What are…

A: The question is based on the concept of Spectroscopy. we have to analyse the spectra provided and…

Q: Propose a structure consistent with following spectral data for a compound C8H18O2

A: Solution-

Q: Draw the structure of a compound with the formula C5H10O2 (along with the reasons of choosing it)…

Q: Treatment of compound D with LiAlH4 followed by H2O forms compound E. D shows a molecular ion in its…

Q: Propose a structure consistent with each set of spectral data: a. C4H8Br2: IR peak at 3000–2850…

A: Hey, since you have asked multiple question, we will solve the first question for you. If you want…

Q: Propose a structure consistent with each set of spectral data: a.C6H14O: IR peak at 3600−3200 cm−1;…

A: Structure consistent with each set of spectral data: a).

Q: Reaction of pentanoyl chloride (CH3CH2CH2CH2COCl) with lithium dimethyl cuprate [LiCu(CH3)2] forms a…

A: The reaction of pentanoyl chloride (CH3CH2CH2CH2COCl) with lithium dimethyl cuprate [LiCu(CH3)2]…

Q: C9H10O2: IR absorption at 1718 cm–1. Propose a structure with data given.

A: C9H10O2: IR absorption at 1718 cm–1. Propose a structure with data given

Q: Propose a structure consistent with each set of data. C8H10 : IR absorptions at 3108–2875, 1606, and…

A: GIVEN: IR absorptions at 3108–2875, 1606, and 1496 cm−1

Q: The IR spectrum of compound A with a molecular formula of C5H12O is shown below. Compound A is…

Q: An compound that has a molecular formula of C5H11NO, has the below 1H NMR spectrum which is showen…

A: The given is an NMR spectrum for the compound having a molecular formula C5H11NO, the NMR and IR…

Q: cyclohexanone 1-methylcyclopentanecarbaldehyde

A: We know that the 1H- NMR spectroscopy predicts the number of chemically distinct protons present in…

Q: Which compound below has a strong IR absorption at 1715 cm¹ and shows prominent peaks in the mass…

A: IR spectroscopy is used to determine the functional groups present in the sample. Different…

Q: 3H, t 1Η ΝMR 2H, q 1H,broad Disappears when 1 drop of D20 was added. 12 11 10 8. 6. 4 2

A: The correct structure of the above spectral data is propanoic acid. this is mostly confirmed by the…

Q: Propose a structure consistent with following set of spectral data: C3H6Br2: IR peak at 3000–2850…

A: Given, C3H6Br2: IR peak at 3000–2850 cm−1; NMR (ppm): 2.4 (quintet) 3.5 (triplet)

Q: Compound C has a molecular weight of 94.54 and the ¹H-NMR spectrum shows four signals - a triplet at…

A: Please find the attachment.

Q: Oxidation of citronellol, a constituent of rose and geranium oils, with PCC in the presence of added…

Q: Treatment of benzaldehyde (C6H5CHO) with Zn(Hg) in aqueous HCl forms a compound Z that has a…

A: Aldehydes or ketones undergoes reduction to form hydrocarbons when treated with Zn(Hg) in the…

Q: Following is H-NMR of compound A . Compound A is comprised of H, C and O atoms. In mass spectrum,…

A: IHD = Number of Pi bonds or ring

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

Propose a structure consistent with following set of spectral data:

C₅H₁₀O₂: IR peak at 1740 cm⁻¹; NMR (ppm):

1.15 (triplet, 3 H) 2.30 (quartet, 2 H)

1.25 (triplet, 3 H) 4.72 (quartet, 2 H)

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

Trending now

This is a popular solution!

Step by step

Solved in 2 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

Identify A and B, isomers of molecular formula C3H4Cl2, from the given 1H NMR data: Compound A exhibits peaks at 1.75 (doublet, 3 H, J = 6.9 Hz) and 5.89 (quartet, 1 H, J = 6.9 Hz) ppm. Compound B exhibits peaks at 4.16 (singlet, 2 H), 5.42 (doublet, 1 H, J = 1.9 Hz), and 5.59 (doublet, 1 H, J = 1.9 Hz) ppm.
Identify the structures (molecular formula C9H10O). I R peak at 1688 cm−1; 1H NMR data (ppm) at 1.22 (triplet, 3 H), 2.98 (quartet, 2 H), and 7.28–7.95 (multiplet, 5 H).
Propose a structure consistent with following set of spectral data: C3H6O: IR peak at 1730 cm−1; NMR (ppm): 1.11 (triplet) 2.46 (multiplet) 9.79 (triplet)
A compound with molecular mass 114 and in IR spectrum, absorption bands are formed at 1770 cm¹ (s), 1650 cm-¹ (m) and 1200 cm¹ (w). In ¹H NMR six signals are observed, 8 1.0 (t, 3H), 1.7 (m 2H), 2.4 (t, 2H), 4.6 (d, 1H), 4.9 (d, 1H), 7.4 (d, 1H). Predict the molecular structure of the unknown compound and justify your answer.
Propose a structure consistent with each set of spectral data: a.C6H14O: IR peak at 3600−3200 cm−1; NMR (ppm): 0.8 (triplet, 6 H) 1.5 (quartet, 4 H) 1.0 (singlet, 3 H) 1.6 (singlet, 1 H) b.C6H14O: IR peak at 3000−2850 cm−1; NMR (ppm): 1.10 (doublet, relative area = 6) 3.60 (septet, relative area = 1)
Please show complete answer. Propose a structure consistent with following set of spectral data: a. C5H10O2: IR peak at 1740 cm−1; NMR (ppm): 1.15 (triplet, 3 H) 2.30 (quartet, 2 H) 1.25 (triplet, 3 H) 4.72 (quartet, 2 H) b. C3H6O: IR peak at 1730 cm−1; NMR (ppm): 1.11 (triplet) 2.46 (multiplet) 9.79 (triplet)
Reaction of butanenitrile (CH3CH2CH2CN) with methylmagnesium bromide (CH3MgBr), followed by treatment with aqueous acid, forms compound G. G has a molecular ion in its mass spectrum at m/z = 86 and a base peak at m/z = 43. G exhibits a strong absorption in its IR spectrum at 1721 cm−1 and has the 1H NMR spectrum given below. What is the structure of G? We will learn about the details of this reaction in Chapter 22.
Reaction of butanenitrile (CH3CH2CH2CN) with methylmagnesium bromide (CH3MgBr), followed by treatment with aqueous acid, forms compound G. G has a molecular ion in its mass spectrum at m/z = 86 and a base peak at m/z = 43. G exhibits a strong absorption in its IR spectrum at 1721 cm−1 and has the 1H NMR spectrum given below. What is the structure of G?
Propose a structure for a compound that displays the given spectroscopic data. The molecular ion in the mass spectrum appears at m/z = 116. IR: 1710 (s) and 3000 (s, broad) cm¹. ¹H NMR: 8 = 0.94 (t, J = 7.0 Hz, 6H), 1.59 (m, 4H), 2.36 (quintet, J = 7.0 Hz, 1H) and 12.04 (broad s, 1H) ppm. 13C NMR: 8 = 11.7, 24.7, 48.7, and 183 ppm. Deduce the structure. Select 11 ||| ||| Q Search Draw C H O • Templates More Question Source: Vollhardt 7e - Organic Chemistry: Structure And Function P W Erase Publisher: W.H. Freeman ENG 4: 4/18
Give the structure that corresponds to the following molecular formula and ¹H NMR spectrum:: C₂H₁604: 8 1.93 (t, J = 6 Hz); 8 3.35 (s); 8 4.49 (t, J = 6 Hz); relative integral 1:6:1. 16 Draw the structure. Select Draw Rings More C H O
G.5 Mass spectra were acquired for 1,4-diethylbenzene and 1-methyl-4- propylbenzene. The base peak of spectrum A is at m/z = 105 and that of spectrum B is at mlz = 119. Match each spectrum to its compound.
Propose a structure consistent with each set of spectral data: a. C4H8Br2: IR peak at 3000–2850 cm−1; NMR (ppm): 1.87 (singlet, 6 H) 3.86 (singlet, 2 H) b.C3H6Br2: IR peak at 3000–2850 cm−1; NMR (ppm): 2.4 (quintet) 3.5 (triplet) c. C5H10O2: IR peak at 1740 cm−1; NMR (ppm): 1.15 (triplet, 3 H) 2.30 (quartet, 2 H) 1.25 (triplet, 3 H) 4.72 (quartet, 2 H) d.C3H6O: IR peak at 1730 cm−1; NMR (ppm): 1.11 (triplet) 2.46 (multiplet) 9.79 (triplet)