22. A compound has a strong absorption in the infrared spectrum near 1700 cm and molecular lons at m/z 166 and168 in a 1:1 ratio in its mass spectrum. The 'H NMR spectrum is given below. Give a structure consistent with thesedata.PPMT7

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

A compound strong absorption in infrared spectrum near 1700 cm" and molecular ions at m/z 166 and 168 in a 1:1 ratio in its mass spectrum. The 'H NMR spectrum is given below. Give a structure consistent with these data. PPM 6.

A compound strong absorption in infrared spectrum near 1700 cm" and molecular ions at m/z 166 and 168 in a 1:1 ratio in its mass spectrum. The 'H NMR spectrum is given below. Give a structure consistent with these data. PPM 6.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter12: Structure Determination: Mass Spectrometry And Infrared Spectroscopy

Section12.SE: Something Extra

Problem 48AP: The infrared spectrum of the compound with the mass spectrum shown below lacks any significant...

See similar textbooks

Related questions

Q: How could 1H NMR spectroscopy be used to distinguish among isomersA, B, and C?

A: It is type of spectroscopy called as Nuclear Magnetic resonance spectroscopy. It is analytical tool…

Q: Choose the structure corresponding to the given 1H and 13C NMR spectra

Q: Assume that you have a compound with the formula C4H8O. a) How many double bonds and/or rings does…

A: The structure of any organic compound can be accurately determine with help of spectroscopy…

Q: Treatment of isobutene [(CH3)2C=CH2] with (CH3)3CLi forms a carbanionthat reacts with CH2=O to form…

A: Given information, The reaction of isobutene [(CH3)2C = CH2] with (CH3)3CLi forms a carbanion…

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

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: Reaction of tert-butyl pentyl ether [CH3CH2CH2CH2CH2OC(CH3)3] with HBr forms 1-bromopentane…

A: In the given reaction of tert - Butyl pentyl ether with HBr, bromide ion reacts with protonated form…

Q: Compound A has prominent infrared absorptions at 1050, 1786, and 1852 cm and shows a single…

Q: In the presence of a small amount of acid, a solution of acetaldehyde (CH3CHO) in methanol (CH3OH)…

A: Aldehyde react with alcohol and form hemiacetal molecule. Further reaction form acetal. Acetal has…

Q: C-NMR analysis on the molecule hexaphenylbenzene.

A: C-13 NMR of hexaphenylbenzene.

Q: Reaction of butanenitrile (CH3CH2CH2CN) with methylmagnesium bromide (CH3MgBr), followed by…

A: The reaction involved is shown below.

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: In the presence of a small amount of acid, a solution of acetaldehyde (CH3CHO) in methanol (CH3OH)…

A: The 1H NMR spectrum contains three signals indicating three proton environments in the organic…

Q: Reaction of 2-methylpropanoic acid [(CH3)2CHCO2H] with SOCl2 followed by 2-methylpropan-1-ol forms…

Q: Treatment of ketone A with ethynyllithium (HC≡CLi) followed by D3O+ afforded a compound B of…

Q: Treatment of compound D with LIAIH4 followed by H2O forms compound E. D shows a molecular ion in its…

A: Spectroscopy deals with the transitions that a molecule undergoes between its energy levels upon…

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

Q: (a) The 'H-NMR spectrum of cyclobutanone shows two signals - signal A at 3.00 ppm and signal B at…

A: “Since you have asked multiple question, we will solve the first question for you. If youwant any…

Q: (b) An organic compound (A), having MF C,H120 reduces Fehling solution and Tollens reagent. The…

A: Compound A reduces the Tollens reagent. Therefore the compound is aldehyde ( see the fragmentation…

Q: Reaction of butanenitrile (CH3CH2CH2CN) with methylmagnesium bromide (CH3MgBr), followed by…

A: The reaction of butanenitrile with methyl magnesium bromide followed by treatment with aqueous acid…

Q: Compound Y (molecular formula C6H10) gives four lines in its 13C NMRspectrum (27, 30, 67, and 93…

Q: Compound A (C1,H14) shows prominent peaks in its mass spectrum at m/z 134 and 91. Compound B (also…

A: The double bond equivalent of compound A and compound B is same. The double bond equivalent of the…

Q: Q1-Deduce the structures of isomeric compounds (A) and (B) having molecular formula C3H,0 and the…

A: Please note- As per our company guidelines we are supposed to answer only one question. Kindly…

Q: Benzonitrile (C6H5CN) is reduced to two different products depending on the reducing agent used.…

Q: Suggest a structure, which is consistent with the IR and 1 H NMR spectra as shown below. (C,H,0,)…

Q: Treatment of anisole (CH3OC6H5) with Cl2 and FeCl3 forms P, which has peaks in its mass spectrum at…

A: The chemical reaction between anisole and chlorine molecule in presence of ferric chloride is given…

Q: The IR, 'H NMR and 13C NMR spectre of compound P are shown below. The molecular formuls for compound…

A: The solution is as follows:

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: A molecule of the molecular formula C5H11B gives rise to the NMR spectrum below. When reacted with…

Q: Treatment of isobutene [(CH3)2C = CH2] with (CH3)3CLi forms a carbanion that reacts with CH2=O to…

A: The reaction of isobutene [(CH3)2C = CH2] with (CH3)3CLi forms a carbanion that reacts with CH2 = O…

Q: 10. (a) Give reasons, arrange the following compounds in order of decreasing frequency of carbonyl…

A: For finding decreasing order, all the IR values have to be found, the carbonyl frequency decreases…

Q: Calculate the IHD and explain (elucidate) the structure using the 1H and 13C NMR data.

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

Q: Treatment of compound D with LIAIH, followed by H,O forms compound E. D shows a molecular ion in its…

A: From given IR spectra We are depicting peak value for both compound D and E and from that we are…

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: reatment of molecule A with Mg forms a Grignard reagent that reacts with CH,=0 to form H aft ater is…

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

Q: A two-step synthesis of virstatin reactions are given. Give the yield and % yield of each synthesis.…

A: Since you have asked a question with multiple sub-part, we will solve the yield and percent yield…

Q: 6. Draw a structure for a compound that meets the following description: C7H8 with IR absorptions at…

A: Part - 1 IR spectrum Sr no peak (cm-1) assignment 1 1600 due to aromatic C =C stretching…

Concept explainers

Mass Spectrometry

This process is an instrumental method in which a sample is changed to fast moving positive ions by electron bombardment. The charged particles vary due to their different mass to charge ratio and are estimated with the help of this difference. It is also called mass spectroscopy.

Question

22. A compound has a strong absorption in the infrared spectrum near 1700 cm and molecular lons at m/z 166 and
168 in a 1:1 ratio in its mass spectrum. The 'H NMR spectrum is given below. Give a structure consistent with these
data.
PPM
T7

Expert Solution

This question has been solved!

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

SEE SOLUTION Check out a sample Q&A here

Step 1

VIEW

Step 2

VIEW

Step by step

Solved in 2 steps with 1 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

3-Chlorocyclopropene, on treatment with AgBF4, gives a precipitate of AgCl and a stable solution of a product that shows a single 1H NMR absorption at 11.04 Î´. What is a likely structure for the products, and what is its relation to HĂ¼ckelâ€™s rule?
Compound A, a hydrocarbon with M+=96 in its mass spectrum, has the 13C spectral data given below. On reaction with BH3, followed by treatment with basic H2O2. A is converted into B, whose, 13C spectral data are also given below. Propose structures for A and B. Compound A Broadband-decoupled l3C NMR: 26.8, 28.7, 35.7, 106.9, 149.7 DEPT-90: no peaks DEPT-135: no positive peaks; negative peaks at 26.8, 28.7, 35.7, 106.9 Compound B Broadband-decoupled 13C NMR: 26.1, 26.9, 29.9, 40.5, 68.2 DEPT-90: 40.5 DEPT-135: positive peak at 40.5 ; negative peaks at 26.1, 26.9. 29.9, 68.2
The infrared spectrum of the compound with the mass spectrum shown below lacks any significant absorption above 3000 cm-1. There is a prominent peak near 1740 cm-1 and another strong peak near 1200 cm-1. Propose a structure consistent with the data.
When measured on a spectrometer operating at 200 MHz, chloroform (CHCl3) shows a single sharp absorption at 7.3 Î´. (a) How many parts per million downfield from TMS does chloroform absorb? (b) How many hertz downfield from TMS would chloroform absorb if the measurement were carried out on a spectrometer operating at 360 MHz? (c) What would be the position of the chloroform absorption in Î´ units when measured on a 360 MHz spectrometer?
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.
Treatment of anisole (CH3OC6H5) with Cl2 and FeCl3 forms P, which has peaks in its mass spectrum at m/z = 142 (M), 144 (M + 2), 129, and 127. P has absorptions in its IR spectrum at 3096–2837 (several peaks), 1582, and 1494 cm-1. Propose possible structures for P.
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?
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.
How could 1H NMR spectroscopy be used to distinguish among isomersA, B, and C?
An unknown compound D exhibits a strong absorption in its IR spectrumat 1692 cm−1. The mass spectrum of D shows a molecular ion at m/z =150 and a base peak at 121. The 1H NMR spectrum of D is shown below.What is the structure of D?
In the presence of a small amount of acid, a solution of acetaldehyde (CH3CHO) in methanol (CH3OH) was allowed to stand and a new compound L was formed. L has a molecular ion in its mass spectrum at 90 and IR absorptions at 2992 and 2941 cm−1. L shows three signals in its 13C NMR at 19, 52, and 101 ppm. The 1H NMR spectrum of L is given below. What is the structure of L?
A compound used as a moth repellant has three molecular ion peaks at m/z = 146 (100%), 148 (65%) & 150 (10%) amu in its mass spectrum. A pair of smaller peaks are seen at m/z= 111 (34%) & 113 (11%). The infrared spectrum shows sharp absorption just above 3000 cm^-1 region, and also at 1480 cm^-1. The ^1 H nmr shows a single sharp signal at delta = 7.2 ppm, and the ^13 C nmr has two signals (delta = 133 & 130 ppm).