Propose a structure for the carboxylic acid, C7H14O2, with the following 13C and DEPT NMR data: 185.4 (4°), 42.9 (2º), 42.2 (4°), 25.0 (1), 18.2 (2º), 14.5 (1°) ppm.
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- 19-33 Rank the amines in each set in order of increasing basicity. (b) sbims ne (a) NH2 NH2 N. H (c) H (d) NH2 NH2 NH2 H3C H2 (е) NH2 CH,NH, CONH,Propose a structure for an amine with molecular formula CGH7N by interpreting the given 'H and 13C NMR data below. 1H NMR O 2.35 ppm O7.10 ppm 8 8.46 ppm singlet (3) doublet (2) doublet (2) 13C NMR 2, 4 1,5 6.00- 5.00- 4.00- 3.00- 2.00- 1.00- 0.00- 200 120 100 8/ ppm 180 160 140 80 60 40 20Phthalic acid and isophthalic acid have protons on two carboxy groups that can be removed with base. (a) Explain why the pKa for loss of the first proton (pKa1) is lower for phthalic acid than isophthalic acid. (b) Explain why the pKa for loss of the second proton (pKa2) is higher for phthalic acid than isophthalic acid.
- Electrostatic potential maps of anisole and thioanisole are shown. Which do you think is the stronger acid, p-methoxybenzoic acid or p-(methylthio)benzoic acid? Explain.As far back as the 16th century, South American Incas chewed the leaves of the coca bush, Erythroxylon coca, to combat fatigue. Chemical studies of Erythroxylon coca by Friedrich Wöhler in 1862 resulted in the discovery of cocaine, C17H21NO4, as the active component. Basic hydrolysis of cocaine leads to methanol, benzoic acid, and another compound called ecgonine, C9H15NO3. Oxidation of ecgonine with CrO3 yields a keto acid that readily loses CO2 on heating, giving tropinone. (a) What is a likely structure for the keto acid? (b) What is a likely structure for ecgonine, neglecting stereochemistry? (c) What is a likely structure for cocaine, neglecting stereochemistry?Phthalic acid and isophthalic acid have protons on two carboxy groupsthat can be removed with base. (a) Explain why the pKa for loss of thefirst proton (pKa1) is lower for phthalic acid than isophthalic acid. (b)Explain why the pKa for loss of the second proton (pKa2) is higher forphthalic acid than isophthalic acid.
- The 1H NMR spectrum of 2-chloroacetamide (ClCH2CONH2) shows three signals at 4.02, 7.35, and 7.60 ppm. What protons give rise to each signal? Explain why three signals are observed.Phthalic acid and isophthalic acid have protons on two carboxy groups that can be removed with base. (a) Explain why the pKa for loss of the first proton (pKa1) is lower for phthalic acid than isophthalic acid. (b) Explain why the pKa for loss of the second proton (pKa2) is higher for phthalic acid than isophthalic acid.Phthalic acid and isophthalic acid have protons on two carboxy groups that can be removed with base. (a) Explain why the pKa for loss of the rst proton (pKa1) is lower for phthalic acid than isophthalic acid. (b) Explain why the pKa for loss of the second proton (pKa2) is higher for phthalic acid than isophthalic acid.
- ¹H NMR spectroscopic data for propofol is as follows: 8 1.14 ppm (12H, doublet); 3.05 ppm (2H, multiplet); 7.09 ppm (1H, triplet); 7.25 ppm (2H, doublet); 7.6 ppm (1H, singlet). Match each NMR signal to the corresponding proton on the structure of propofol. OH propofol. Propose a structure for a compound CH12O2 that dissolves in dilute NAOH and shows the following 'H NMR spectrum: 1.08 8 (9H, singlet), 2.2 8 (2H, singlet), and 11.2 8 (1H, singlet).PQ-20. This type of reaction, typical of carboxylic acids, esters, acid halides, anhydrides and amines, is called: (A) a bimolecular nucleophilic substitution. (C) an electrophilic substitution. (A) (A) H3C-C-OCH₂CH3 OH R CI PQ-21 What would be hydrolyzed most slowly with aqueous NaOH? lo (B) OH₂ (C) H3C-C-OCH₂CH3 H3C-C- H CI + H₂O (B) a nucleophilic addition. (D) a nucleophilic acyl substitution. (C) PQ-22. Which structure is a reasonable intermediate in the acid-catalyzed hydrolysis of ethyl acetate, shown, in dilute aqueous acid? RiOH OH (D) H3C- (D) OH (B) H3C-C-OCH₂CH3 OH₂ + HCI si in