2. 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)
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- Reaction of p-cresol with two equivalents of 2-methylprop-1-ene affordsBHT, a preservative with molecular formula C15H24O. BHT gives thefollowing 1H NMR spectral data: 1.4 (singlet, 18 H), 2.27 (singlet, 3 H), 5.0(singlet, 1 H), and 7.0 (singlet, 2 H) ppm. What is the structure of BHT?Draw a stepwise mechanism illustrating how it is formed.Propose a structure for a C,H150,N compound that is unstable in aqueous acid and has the given NMR spectra. 'H NMR: 8 2.30 (6H, s); 8 2.45 (2H, d, J = 6 Hz); 8 3.27 (6H, s); 8 4.50 (1H, t, J = 6 Hz) 13C NMR: 8 46.3, 8 53.2, 8 68.8, 8 102.4 Draw C,H1502N. Select Draw Rings More C N APR étv N Aa MacBook Air4. 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)
- 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. 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?Predict the product based on the following data: H-NMR: 0.93 ppm (3H, triplet); 1.57 ppm (2H, multiplet – looks like “pentet”); 2.14 ppm (3H,singlet), 2.26ppm (2H, triplet); 3.42 ppm (1H, triplet); 4.83 ppm (1H, multiplet) Weight of product: 156 g/mol IR: Two sharp peaks at 1784 cm-1 and 1742 cm-1 C-NMR: 9.9 ppm; 29.0 ppm; 29.8 ppm; 31.8 ppm; 52.9 ppm; 76.1 ppm; 181.1 ppm; 200.2 ppm
- 1. What spectral features allow you to differentiate the product from the starting material? Mass Spec: IR: H NMR: C NMR:Reaction of p-cresol with two equivalents of 2-methylprop-1-ene affords BHT, a preservative with molecular formula C15H24O. BHT gives the following 1H NMR spectral data: 1.4 (singlet, 18 H), 2.27 (singlet, 3 H), 5.0 (singlet, 1 H), and 7.0 (singlet, 2 H) ppm. What is the structure of BHT? Draw a stepwise mechanism illustrating how it is formed.Reaction between this aldehyde and ketone in base gives a compound A with the proton NMR spectrum: ô 1.10 (9H, s), 1.17 (9H, s), 6.4 (1H, d, J 15), and 7.0 (1H, d, J 15). What is its structure? (Don't forget stereochemistry!). When this compound reacts with HBr it gives compound B with this NMR spectrum: õu 1.08 (9H, s), 1.13 (9H, s), 2.71 (1H, dd, J 1.9, 17.7), 3.25 (dd, J10.0, 17.7), and 4.38 (1H, dd, J 1.9, 10.0). Suggest a structure, assign the spectrum, and give a mechanism for the formation of B. H base C11H₂00 HBr B C11H₂1 Bro
- The compound that exhibits the following spectral data is IR: 1740 cm. 1H NMR: 6 0.9(t, 3H), 1.6(sext, 2H), 2.3(1,2H), 4.6(d, 2H), 5.2(d, 1H), 5.4(d, 1H), 5.9(m, 1H) ppm. El-MS(m/z): 71 (100%) O ОA compound (C3H,NO) gives the following NMR data. In the box below please draw the structure of the compound. 'H-NMR: 2.06 ppm, s(3H); 7.01 ppm, t(1H); 7.30 ppm, m(2H); 7.59 ppm, d(2H); 9.90 ppm, s(1H) 13C-NMR: 168.14; 139.24; 128.511; 122.834; 118.90; 23.93 • You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. Do not include lone pairs in your answer. They will not be considered in the grading.2. Provide the structure of E-2,5-dimethyloct-5-enoic acid. 3. a. Name the structure with the following 'H NMR spectrum. 8 (ppm) = 12.71 (1H, s), 8.04 (2H, d), 7.30 (2H, d), 2.41 (3H, s)