Concept explainers
Reaction of butanenitrile (
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Chapter 20 Solutions
Organic Chemistry
- Ketones undergo a reduction when treated with sodium borohydride, NaBH4. What is the structure of the compound produced by reaction of 2-butanone with NaBH4 if it has an IR absorption at 3400 cm-1 and M+=74 in the mass spectrum?arrow_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_forwardCompound H (C8H6O3) gives a precipitate when treated with hydroxylamine in aqueous ethanol and a silver mirror when treated with Tollens solution. Following is its 1H-NMR spectrum. Deduce the structure of compound H.arrow_forward
- Propose a structural formula for the analgesic phenacetin, molecular formula C10H13NO2, based on its 1H-NMR spectrum.arrow_forwardAnethole, C10H12O, a major constituent of the oil of anise, has the 1H NMR spectrum shown. On oxidation with Na2Cr2O7, anethole yields p-methoxybenzoic acid. What is the structure of anethole? Assign all peaks in the NMR spectrum, and account for the observed splitting patterns.arrow_forwardC5H10O2 H Determine H and C Spectra for the compundarrow_forward
- An unknown compound D exhibits a strong absorption in its IR spectrum at 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?arrow_forwardAn unkown compound, which is insoluable in water but soluble in 10% aqueous sodium bicarbonate, yielded the given 1H NMR spectrum. What is the compound?arrow_forwardTreatment of butan-2-one (CH3COCH2CH3) with strong base followed by CH3I forms a compound Q, which gives a molecular ion in its mass spectrum at 86. The IR (> 1500 cm−1 only) and 1H NMR spectra of Q are given below. What is the structure of Q?arrow_forward
- Treatment of butan-2-one (CH3COCH2CH3) with strong base followed by CH3I forms a compound Q, which gives a molecular ion in its mass spectrum at 86. The IR (> 1500 cm−1 only) and 1H NMR spectrum of Q are given below. What is the structure of Q?arrow_forwardCompound P has molecular formula C5H9ClO2. Deduce the structure of Pfrom its 1H and 13C NMR spectra.arrow_forwardGive and explain the analysis of H-NMR and C-NMR spectra of the followingarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning