the (A) Predict the product(s) of the following synthetic transformations: (B) Name each reaction (reaction type): (C) Make sure the NMR of the final product matches your structure: 8 7 6 -5 4 3 2 1 PPM 4 0
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- As we will learn in Chapter 17, 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−1. 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?The enamine prepared from acetone and dimethylamine is shown here in its lowest-energy form. (a) What is the geometry and hybridization of the nitrogen atom? (b) What orbital on nitrogen holds the lone pair of electrons? (c) What is the geometric relationship between the p orbitals of the double bond and the nitrogen orbital that holds the lone pair? Why do you think this geometry represents the minimum energy?Compounds A and B are isomers having the molecular formula C4H8O3. Identify A and B on the basis of their 1H NMR spectra.Compound A: δ 1.3 (3H, triplet); 3.6 (2H, quartet); 4.1 (2H, singlet); 11.1 (1H, broad singlet)Compound B: δ 2.6 (2H, triplet); 3.4 (3H, singlet); 3.7 (2H triplet); 11.3 (1H, broad singlet)
- Which is the stronger acid in each of the following pairs? Explain your reasoning. (a) Phenol or p-hydroxybenzaldehyde (b) m-Cyanophenol or p-cyanophenol (c) o-Fluorophenol or p-fluorophenolAs 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?1 (a) In the following reactions, CI (1) LIAIH, A (2) H20 MCPBA (i) Draw the structure of compounds A and B. (ii) For each reaction, explain the type of reaction involved. (iii) Explain the successful transformation of compound A using mass spectra. (b) Complete the following reactions by filling in missing reactants or product. (i) (1) O3 (2) CH;SCH3 (ii) он (CH3)3(COOH) D Ti(OCH(CH3)2l4 (-)-DET
- 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) ppm(d) When a primary amine is combined with a ketone, both an imine and an enamine can be obtained. With most ketones, the major product is the imine, as shown: H3C NH2 -N -CH3 -CH3 imine: major product enamine: minor product However, in some cases, like the one shown below, the major product is the enamine. CO₂Et CO₂Et CO₂Et H H3C NH2 -CH3 imine: minor product -CH3 enamine: major product Referring to specific features of the starting materials, intermediates, or products, explain why.Predict the major products formed when benzoyl chloride (PhCOCl) reacts with the following reagents.(a) ethanol (b) sodium acetate (c) aniline
- Consider the tetracyclic aromatic compound drawn below, with rings labeled as A, B, C, and D. (a) Which of the four rings is most reactive in electrophilic aromatic substitution? (b) Which of the four rings is least reactive in electrophilic aromatic substitution? (c) What are the major product(s) formed when this compound is treated with one equivalent of Br2?In each of the following compounds, a particular atom is indicated with an ar- row. Determine whether this atom is nucleophilic, electrophilic, acidic. Some atoms may have none or more than one of these properties. (a) (b) O O (d) H3C H₂C CH3 CH3 + -OH₂ (e) (h) H3C H3C CH3 + OH₂ MgBr (c) (f) (i) H3C H3C O CH3 ÓH₂ O MgBrReaction of (CH3)3CCHO with (C6H5)3P=C(CH3)OCH3, followed by treatment 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 the structure of R? We will learn about this reaction in Chapter 18.
