Propose a structural formula for compound J (C,H,,0,) consistent with its 'H-NMRand infrared spectra.CH1403Compound J3H3H2H2H2H2H10875320 ppmChemical shift (8)Micrometers2.5100* 9 108111213 14 15209080706050403020CH1403Compound J1040003600320028002400200018001600140012001000800600400Wavenumber (cm-)Transmittance (%)

Introduction: Infrared spectroscopy is used to detect the functional group in a molecule and nuclear…

Answered: Propose a structural formula for…

Macroscale and Microscale Organic Experiments

7th Edition

ISBN:9781305577190

Author:Kenneth L. Williamson, Katherine M. Masters

Publisher:Kenneth L. Williamson, Katherine M. Masters

Chapter13: Mass Spectrometry

Section: Chapter Questions

Problem 3Q

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Propose a structure consistent with each set of data. C10H14: IR absorptions at 3150–2850, 1600, and 1500 cm−1
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)
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 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).
Treatment of butan-2-one (CH3COCH2CH3) with strong base followed byCH3I forms a compound Q, which gives a molecular ion in its massspectrum at 86. The IR (> 1500 cm−1 only) and 1H NMR spectra of Q aregiven below. What is the structure of Q?
Reaction of pentanoyl chloride (CH3CH2CH2CH2COCl) with lithium dimethyl cuprate [LiCu(CH3)2] forms a compound J that has a molecular ion in its mass spectrum at 100, as well as fragments at m/z = 85, 57, and 43 (base). The IR spectrum of J has strong peaks at 2962 and 1718 cm-1. Propose a structure for J.
A hydrocarbon, compound B, has molecular formula C6H6, and gave an NMR spectrum with two signals: delta 6.55 pm and delta 3.84 pm with peak ratio of 2:1. When warmed in pyridine for three hr, compound B quantitatively converts to benzene. Mild hydrogenation of B yielded another compound C with mass spectrum of m/z 82. Infrared spectrum showed no double bonds; NMR spectrum showed one broad peak at delta 2.34 ppm. With this information, address the following questions. a) How many rings are in compound C? b) How many rings are probably in B? How many double bonds are in B? c) Can you suggest a structure for compounds B and C? d) In the NMR spectrum of B, the up-field signal was a quintet, and the down field signal was a triplet. How must you account for these splitting patterns?
The NMR spectra for compound 1 were acquired in a 7.5 mg / 0.6 mL solution ofCDCl3 . The 1H and 13C peaks are also listedbelow. Provide a full analysis of the NMR spectra for compound 1. correct assignment of NMR spectra of both 13C spectra. correct rationalisation of 13C spectrum1H NMR (400 MHz, CDCl3) δ 7.73 (d, J = 9.5 Hz, 1H), 7.56 (ddd, J = 8.5, 7.5, 1.6 Hz, 1H),7.51 (dd, J = 7.5, 1.6 Hz, 1H), 7.36 (d, J = 8.5 Hz, 1H), 7.30 (dd, J = 8.5, 7.5 Hz, 1H), 6.45(d, J = 9.5 Hz, 1H).13C NMR (101 MHz, CDCl3) δ 160.79, 154.09, 143.43, 131.85, 127.87, 124.44, 118.86,116.94, 116.74.Note: There are two carbon peaks in the 13C spectrum that are so close together that they are not differentiable at the resolution in this experiment. you should be able to assign these peaks to one of two carbon atoms in 1.
Compound A is a hydrocarbon with a molar mass of 96g/mol, with the given C13 spectral data. When compound A reacts with BH3 followed by the treatment with basic H2O2 it is converted to compound B. Propose structures for A and B, explain your analysis.Compound A- Proton decoupled C NMR: 26.8, 28.7, 35.7, 106.9, 149.7 δ.DEPT-90: No peak.DEPT-135: No positive peaks; negative peaks at 26.8, 28.7, 35.7, 106.9 δ.Compound B- Proton decoupled C NMR: 26.1, 26.9, 29.9, 40.5, 68.2 δ.DEPT-90: 40.5 δ.DEPT-135: positive peak at 40.5 δ; negative peaks at 26.1, 26.9, 29.9, 68.2 δ
compound with the molecular formula C7H9N exhibits IR bands at 3450 cm-1 (medium, doublet), and 855 cm-1 (strong) and shows the following major mass spectral signals (m/z): 106 (base); 107 (M+, about 70% of base), 91 (40% of base), and 77 (about 20% of base). Deduce a reasonable structure from this data.
For each compound shown below,(1) sketch the 13C NMR spectrum (totally decoupled, with a singlet for each type of carbon), showing approximatechemical shifts.(2) show the multiplicity expected for each signal in the off-resonance-decoupled spectrum.(3) sketch the spectra expected using the DEPT-90 and DEPT-135 techniques. 3-chloropropene
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?

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