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Interpretation:
The compound between vanillin and isovanillin that would have a
Concept introduction:
Spectroscopy method is used to identify the structure of the molecule. It is based on the interactions between matter and
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Organic Chemistry Study Guide and Solutions
- 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?arrow_forwardAs we will learn in Chapter 20, reaction of (CH3)2CO with LiC ≡ CH followed by H2O affords compound D, which has a molecular ion in its mass spectrum at 84 and prominent absorptions in its IR spectrum at 3600–3200, 3303, 2938, and 2120 cm. D shows the following 1H NMR spectral data: 1.53 (singlet, 6 H), 2.37 (singlet, 1 H), and 2.43 (singlet, 1 H) ppm. What is the structure of D?arrow_forwardIs it possible to distinguish between the following compounds using the spectroscopic techniques covered in CHE331? If so, discuss how. If not, discuss why.Benzonitrile vs Benzaldehyde(a) UV spectroscopy(b) IR spectroscopy(c) Mass spectrometry(d) 13C NMR spectroscopy(e) 1H NMR spectroscopyarrow_forward
- Treatment of compound E (molecular formula C4H8O2) with excess CH3CH2MgBr yields compound F (molecular formula C6H14O) after protonation with H2O. E shows a strong absorption in its IR spectrum at 1743 cm-1. F shows a strong IR absorption at 3600–3200 cm-1. The 1H NMR spectral data of E and F are given. What are the structures of E and F?Compound E signals at 1.2 (triplet, 3 H), 2.0 (singlet, 3 H), and 4.1 (quartet, 2 H) ppmCompound F signals at 0.9 (triplet, 6 H), 1.1 (singlet, 3 H), 1.5 (quartet, 4 H), and 1.55 (singlet, 1 H) ppmarrow_forwardCompound 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.arrow_forwardAmines suitable for preparing buffers are often synthesized by treating ammonia with epoxides. Consider the following series of reactions, and draw the structure of compound B. NH₂ B You do not have to consider stereochemistry.arrow_forward
- Compound A has molecular formula C8H8O. Its 1H-NMR spectrum shows a singlet of integral 3 at 2.58 ppm and a multiplet of integral 5 at 7.84 ppm. Its 13C-NMR shows six signals. The IR spectrum of A shows a noteworthy stretch at 1698 cm-1. - Identify Compound A, explaining your reasoning Compound A is treated with a mixture of nitric and sulfuric acids to generate Compound B. The 1H-NMR spectrum of B shows three singlets, one at 2.52 pm of integral 3, one at 6.67 ppm of integral 1, and one at 7.94 ppm of integral 2. The 13C-NMR spectrum of B shows six signals. - Identify compound B, explaining your reasoning Compound B is treated with methylmagnesium bromide and then aqueous acid to generate compound C. The 1H-NMR spectrum of C shows four singlets, one at 1.42 ppm of integral 6, one at 2.3 ppm of integral 1, one at 8.52 ppm of integral 2, and one at 8.97 ppm of integral 1. The 13C-NMR spectrum of C shows six signals. The IR spectrum of C shows a noteworthy broad stretch at 3326 cm-1. -…arrow_forwardPlease helparrow_forwardJj.198.arrow_forward
- Treatment of 1,3,6-cyclononatriene (Compound 1), or its dimethyl derivative (Compound 2), with potassium amide (KNH₂) in liquid ammonia results in the formation of anion 1a or 2a, respectively (J. Am. Chem. Soc. 1973, 95, 3437-3438): 9 15.85a 2 6 3 4 5 Compound 1 (R=H) Compound 2 (R=CH3) * You answer is incorrect. KNH₂ KNH₂ 1a (anion) 2a (anion) Of the following, which is NOT one of the four resonance structures of 1a?arrow_forwardIdentify products A and B from the given 1H NMR data. Treatment of acetone [(CH3)2C=O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1H NMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1H) ppm. What is the structure of B?arrow_forwardGiven here are 1H-NMR and 13C-NMR spectral data for nine compounds. Each compound shows strong absorption between 1720 and 1700 cm-1 and strong, broad absorption over the region 2500–3300 cm-1. Propose a structural formula for each compound.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning