EBK ORGANIC CHEMISTRY-PRINT COMPANION (
4th Edition
ISBN: 9781119776741
Author: Klein
Publisher: WILEY CONS
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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?
Identify 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?
Propose a structure for each of the following two isomers with formula C6H14 given their 1H-NMR spectra.
Isomer A: δ = 0.84 (d, 12 H), 1.39 (septet, 2H) ppm
Isomer B: δ = 0.84 (t, 3 H), 0.86 (t, 9H), 1.22 (q, 2H) ppm
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- A C5H8 alkyne is reacted with Lindlar's catalyst and hydrogen gas to yield product with the following H NMR resonances. Provide the structure for Product A and the alkyne 0.78 ppm triplet 3H 1.60 ppm doublet 3H 2.05 ppm doublet of quartets 2H 5.40 ppm doublet of quartets 1H 5.34 ppm doublet of triplets 1Harrow_forward2. Fill in the boxes in the following problem. (Hints: The difference between the # of carbons in the product and the # in the starting material tells us the # in the carbonyl. The fact that we form only one product tells us the identity of the carbonyl.) C8H9Br 1H NMR: 7.3-7.1 (m, 5H) 3.5 (t, 2H) 3.1 (t, 2H) 1) Ph3P 2) nBuLi phosphonium ylide carbonyl C1114 (only one product formed)arrow_forwardCancer of the prostate is the second leading cause of cancer deaths among American males, exceeded only by lung cancer. One treatment of prostate cancer is based on the fact that testosterone and androsterone (both androgens) enhance the proliferation of prostate tumors. The drug flutamide (an antiandrogen) reduces the level of androgens in target tissues and is currently used to prevent and treat prostate cancer.Propose a synthesis of flutamide from trifluoromethylbenzenearrow_forward
- 4. The 1H NMR spectrum shown below corresponds to one of the molecules A-D. Identify the molecule and then provide the complete IUPAC name for the molecule. Don't forget about stereochemistry. он ÕH ÕH B D 11 10 8 6 5 1 'H NMR: 3.35 (1H, m), 1.66 (1H, m), 1.36 (9H, m, overlapping signals), 0.91 (6H, d), 0.90 (3H, t)arrow_forwardPropose a synthesis for the following transformation: 1) Reagent 1 CI 1) 2) NaNO2, HCI Compound A AICI 3 3) Reagent 2 4) H₂O*, heat 2) HNO3, H2SO4 Choose from the following list of reagents: A B C D CH3CI CuCN 3 PBr3 E F G Н LAH NBS, heat DMS Fe, H3O+ -COOHarrow_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_forward
- Identify the following compound from its IR and proton NMR spectra. C,H1,0: 'H NMR 8 3.31 (3H, s); 8 2.41 (1H, s); & 1.43 (6H, s) IR: 2110, 3300 cm-1 (sharp) Draw the compound.arrow_forwardThe infrared spectrum of compound A, C,H,0, shows a strong, sharp peak at 1724 cm-1. From this information and its 'H-NMR spectrum, deduce the structure of compound A. CH120 Compound A ЗН 3H 3H IH 2H 10 9. 8. 7 6. 4 3 1 O ppm Chemical shift (8)arrow_forwardReaction of aldehyde D with amino alcohol E in the presence of NaH forms F (molecular formula C11H15NO2). F absorbs at 1730 cm−1 in its IR spectrum. F also shows eight lines in its 13C NMR spectrum, and gives the following 1H NMR spectrum: 2.32 (singlet, 6 H), 3.05 (triplet, 2 H), 4.20 (triplet, 2 H), 6.97 (doublet, 2 H), 7.82 (doublet, 2 H), and 9.97 (singlet, 1 H) ppm. Propose a structure for F. We will learn about this reaction in Chapter 18.arrow_forward
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