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ORGANIC CHEMISTRY W/BIO...-STUD.SOLN.
- Identify products A and B from the given 1H NMR data. a.Treatment of CH2=CHCOCH3 with one equivalent of HCl forms compound A. A exhibits the following absorptions in its 1H NMR spectrum: 2.2 (singlet, 3 H), 3.05 (triplet, 2 H), and 3.6 (triplet, 2 H) ppm. What is the structure of A? b.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 (1 H) ppm. What is the structure of B?arrow_forwardIdentify products A and B from the given 1H NMR data. Treatment of CH2=CHCOCH3 with one equivalent of HCl forms compound A. A exhibits the following absorptions in its 1H NMR spectrum: 2.2 (singlet, 3H), 3.05 (triplet, 2 H), and 3.6 (triplet, 2 H) ppm. What is the structure of A?arrow_forwardReaction of (CH3)3CCHO with (C6H5)3P=C(CH3)OCH3, followed bytreatment with aqueous acid, affords R (C7H14O). R has a strong absorption in its IR spectrum at 1717 cm−1 and three singlets in its 1H NMR spectrum at 1.02 (9 H), 2.13 (3 H), and 2.33 (2 H) ppm. What is thestructure of R?arrow_forward
- When treated with an equivalent of methanol, compound A, with molecular formula C4H6Cl2O, forms the compound whose 1H NMR spectrum is shownhere. Identify compound A.arrow_forwardAn unknown compound A (molecular formula C7H14O) was treated withNaBH4 in CH3OH to form compound B (molecular formula C7H16O).Compound A has a strong absorption in its IR spectrum at 1716 cm−1.Compound B has a strong absorption in its IR spectrum at 3600−3200cm−1. The 1H NMR spectra of A and B are given. What are the structuresof A and B?arrow_forwardIdentify the structure of compound C (molecular formula C11H15NO2), which has an IR absorption at 1699 cm−1 and the 1H NMR spectrum shown below.arrow_forward
- Compound A, C8H10O, has the IR and 1H NMR spectra shown. Propose a structure consistent with the observed spectra, and label each peak in the NMR spectrum. Note that the absorption at 5.5 î disappears when D2O is added.arrow_forwardIdentify the structure of compound C (molecular formula C11H15NO2),which has an IR absorption at 1699 cm−1 and the 1H NMR spectrumshown below.arrow_forwardAn unknown compound C of molecular formula C6H12O3 exhibits a strong absorption in its IR spectrum at 1718 cm−1 and the given 1H NMR spectrum. What is the structure of C?arrow_forward
- Treatment of (CH3)2CHCH(OH)CH2CH3 with TsOH affords two products(M and N) with molecular formula C6H12. The 1H NMR spectra of M and Nare given below. Propose structures for M and N, and draw a mechanismto explain their formation.arrow_forwardCompound A undergoes an acid-catalyzed hydrolysis. One of the products (B) that is isolated gives the following 1H NMR spectrum. Identify the compounds A and Carrow_forward2. DEDUCE THE STRUCTURE FOR EACH COMPOUND WITH THE INDICATED MOLECULAR FORMULA AND THE 1H-NMR AND IR SPECTRA PROVIDED. (c) Formula: C3H6O2arrow_forward