Treatment of benzaldehyde (CgH,CHO) with Zn(Hg) in aqueous HCI forms a compound Z that has a molecular ion at 92 in its mass spectrum. Z shows absorptions at 3150-2950, 1605, and 1496 cm-1 in its IR spectrum. Give a possible structure for Z.
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- Reaction of 2-methylpropanoic acid [(CH3)2CHCO2H] with SOCl2 followed by 2-methylpropan-1-ol forms X. X has a molecular ion at 144 and IR absorptions at 2965, 2940, and 1739 cm-1. Propose a structure for X.Compounds B and C are isomers with molecular formula C5H9BrO2. The 1H NMR spectrum of compounds B and C are shown below. The IR spectrum corresponding to compound B showed strong absorption bands at 1739, 1225, and 1158 cm-1, while the spectrum corresponding to compound C have strong bands at 1735, 1237, and 1182 cm-1. 1.Based on the information provided, determine the structure of compounds B and C. 2.Assign all peaks in 1H NMR spectrum of compounds B and C.A solution of acetone [(CH3)2C=O] in ethanol (CH3CH2OH) in the presence of a trace of acid was allowed to stand for several days, and a new compound of molecular formula C7H16O2 was formed. The IR spectrum showed only one major peak in the functional group region around 3000 cm−1, and the 1H NMR spectrum is given here. What is the structure of the product?
- Propose a structure for a compound with the formula, C4H7ClO2, that has the following IR and1H NMR spectra. Provide spectral analysis.Compound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3, but dissolves readily in 10% Na2CO3 and 10% NaOH. When these alkaline solutions are acidified with 10% HCl, compound I is recovered unchanged. Given this information and its 1H-NMR spectrum, deduce the structure of compound I.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?
- Consider the monosubstituted benzene reagent X. Nitration of X yields product Y. Product Y is analysed by 1H and 13C NMR spectroscopy (see Figures 1 to 4). Determine the structure of X and Y on the basis of the spectral data provided.Although benzene itself absorbs at 128 ppm in its 13C NMR spectrum, the carbons of substituted benzenes absorb either upfield or downfield from this value depending on the substituent. Explain the observed values for the carbon ortho to the given substituent in the monosubstituted benzene derivatives X and Y.γ-Butyrolactone (C4H6O2, GBL) is a biologically inactive compound that is converted to the biologically active recreational drug GHB (Section 19.5) by a lactonase enzyme in the body. Since γ-butyrolactone is more fat soluble than GHB, it is more readily absorbed by tissues and thus produces a faster onset of physiological symptoms. γ-Butyrolactone shows an absorption in its IR spectrum at 1770 cm−1 and the following 1H NMR spectral data: 2.28 (multiplet, 2 H), 2.48 (triplet, 2 H), and 4.35 (triplet, 2 H) ppm. What is the structure of γ-butyrolactone?
- Sketch and explain the IR, UV, mass, and NMR (1H and 13C) spectroscopy data of BenzonitrileReaction of C6H5CH2CH2OH with CH3COCl affords compound W, whichhas molecular formula C10H12O2. W shows prominent IR absorptions at3088–2897, 1740, and 1606 cm−1. W exhibits the following signals in its1H NMR spectrum: 2.02 (singlet), 2.91 (triplet), 4.25 (triplet), and 7.20–7.35(multiplet) ppm. What is the structure of W?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?