Identify the structures of isomers A and B (molecular formula CoH10O).IR peak at 1742 cm; 'H NMR data (ppm) at 2.15 (singlet, 3 H), 3.70 (singlet, 2 H),and 7.20 (broad singlet, 5 H).CompoundA:ionIR peak at 1688 cm; 'H NMR data (ppm) at 1.22 (triplet, 3 H), 2.98 (quartet, 2 H),and 7.28-7.95 (multiplet, 5 H).CompoundB:

The given two compounds (A and B) are isomers with molecular formula C9H10ODetermine double bond…

Answered: Identify the structures of isomers A…

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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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?
Treatment of compound D with LiAlH4 followed by H2O forms compound E. D shows a molecular ion in its mass spectrum at m/z = 71 and IR absorptions at 3600–3200 and 2263 cm–1. E shows a molecular ion in its mass spectrum at m/z = 75 and IR absorptions at 3636 and 3600–3200 cm–1. Propose structures for D and E from these data and the given 1H NMR spectra.
Treatment of isobutene [(CH3)2C=CH2] with (CH3)3CLi forms a carbanionthat reacts with CH2=O to form H after water is added to the reactionmixture. H has a molecular ion in its mass spectrum at m/z = 86, andshows fragments at 71 and 68. H exhibits absorptions in its IR spectrumat 3600−3200 and 1651 cm−1, and has the 1H NMR spectrum given below.What is the structure of H?
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.
Reaction of tert-butyl pentyl ether [CH3CH2CH2CH2CH2OC(CH3)3] with HBr forms 1-bromopentane (CH3CH2CH2CH2CH2Br) and compound B. B has a molecular ion in its mass spectrum at 56 and gives peaks in its IR spectrum at 3150−3000, 3000−2850, and 1650 cm−1. Propose a structure for B, and draw a stepwise mechanism that accounts for its formation.
Treatment of isobutene [(CH3)2C = CH2] with (CH3)3CLi forms a carbanion that reacts with CH2=O to form H after water is added to the reaction mixture. H has a molecular ion in its mass spectrum at m/z = 86, and shows fragments at 71 and 68. H exhibits absorptions in its IR spectrum at 3600–3200 and 1651 cm−1, and has the 1H NMR spectrum given below. Whatis the structure of H?
Complete the following answer using the data provided here: Molecular formula: C4H8O2 Important IR data (cm-1): 3280 (broad); 2980-2730 (many); 1690; 1254 All 1H NMR data (ppm, splitting, integration): 11.0 ppm (s), 1; 2.57 ppm (m), 1; 1.07 ppm (d), 6 1. Sketch out a 1H NMR spectrum showing peak locations and peak splitting on a ppm scale for the data provided above. Include the data labels above in your spectrum, but do not show integration lines. 2. draw the most proper line bond structure for the data given above
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.
The mass spectrum of 1-ethyl-1-methylcyclohexane shows many fragments, with two in very large abundance. Kne appears af m/z=111 and the other appears at m/z=97. Identify the structure of each of these fragments.
The infrared spectrum of the compound with the mass spectrum shown below has a medium-intensity peak at about 1650 cm-1. There is also a C-H out-of-plane bending peak near 880 cm-1. Propose a structure consistent with the data.
Long-range coupling between protons more than two carbon atoms apart is sometimes observed when bonds intervene. An example is found in 1-methoxy-l-buten-3-yne. Not only does the acetylenic proton, Î—a, couple with the vinylic proton Hb, it also couples with the vinylic proton Hc, four carbon atoms away. The data are: Construct tree diagrams that account for the observed splitting patterns of Î—a, Hb, and Hc.
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.

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