Show the structures of the missing substance(s) in each of the following acid-base equilibria. a. CH3-CH2-CH2-NH2 + H,0 = CH3-CH2-CH2-NH3+? b. ? + H20 = CH2-NH, + OH" c. CH3-CH-CH2-NH-CH3 + H2O =?+OH CH3 d. Trimethylamine + H2O = ? + ? 1
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- Amines are weak bases. Table 10.2 in the course textbook provides a list of pKb values for several amines. The pK values for three amines and their structures are shown below. Explain why increased substitution on nitrogen results in an increase of the pKb value. H3C-NH2 PK = 3.36 H3C N-H pKb = 3.27 H₂C' H3C N-CH3 PK = 4.19 H₂CFollowing are structural formulas for phenol and cyclohexanol along with the acid dis- sociation constants for each. OH НО Cyclohexanol pK, 18 Phenol pK, 9.96 Propose an explanation for the fact that phenol is a considerably stronger acid than cyclohexanol.Specialized reagents and their acronyms: MCPBA= meta-chloroperbenzoic acid; HOAC = acetic acid, NaOAc = Sodium Acetate; Ph= phenyl = C6H5-; P(Ph)3 = triphenyl phosphine; NBS = N- bromosuccinimide, PBR3, SOCI2, AICI3, FeBr3, H2SO4, Li, Na, Mg, Br2, CrO3, LDA = lithium diisopropylamide, PCC = pyridinium chlorochromate, KO-C(CH3)3, LAH = LIAIH4, (sia)2BH = disecondary isobutyl borane, KMNO4, HIO4 = periodic acid %3D write the missing reagents and solvents over the arrows. Some transformation require multiple steps. In some cases there will be multiple arrows. Ph -Ph Ph Ph Br
- Specialized reagents and their acronyms: MCPBA= meta-chloroperbenzoic acid; HOAC = acetic acid, NaOAc = Sodium Acetate; Ph= phenyl = C6H5-; P(Ph)3 = triphenyl phosphine; NBS = N- bromosuccinimide, PBr3, SOCI2, AICI3, FeBr3, H2SO4, Li, Na, Mg, Br2, CrO3, LDA = lithium diisopropylamide, PCC = pyridinium chlorochromate, KO-C(CH3)3, LAH = LIAIH4, (sia)2BH = disecondary isobutyl borane, KMNO4, HIO4 = periodic acid %3D %3D %3D %3D %3D write the missing reagents and solvents over the arrows. Some transformation require multiple steps. In some cases there will be multiple arrows. Ph CH CH o 0om ilubongo CEC-Ph In questions 14-24, write the products of the following transformations. If there is no reaction write NR. Indicate R or S or racemic or indicate cis or trans where appropriate OH + LDA THF solvent (S) PhSpecialized reagents and their acronyms: MCPBA= meta-chloroperbenzoic acid; HOAC = acetic acid, NaOAc = Sodium Acetate; Ph= phenyl = C6H5-; P(Ph)3 = triphenyl phosphine; NBS = N- bromosuccinimide, PBR3, SOCI2, AICI3, FeBr3, H2SO4, Li, Na, Mg, Br2, CrO3, LDA = lithium diisopropylamide, PCC = pyridinium chlorochromate, KO-C(CH3)3, LAH = LIAIH4, (sia)2BH = disecondary isobutyl borane, KMNO4, HIO4 = periodic acid %3D %3D %3D %3D %3D %3D %3D write the missing reagents and solvents over the arrows. Some transformation require multiple steps. In some cases there will be multiple arrows. ОН H. (R) Br (S) HO OHSome alcohols undergo rearrangement or other unwanted side reactions when they dehydrate in acid. Alcohols may be dehydrated under mildly basic conditions using phosphorus oxychloride (POCl3) in pyridine. The alcohol reacts with phosphorus oxychloride much like it reacts with tosyl chloride, displacing a chloride ion from phosphorus to give an alkyl dichlorophosphate ester. The dichlorophosphate group is an outstanding leaving group. Pyridine reacts as a base with the dichlorophosphate ester to give an E2 elimination. Propose a mechanism for the dehydration of cyclohexanol by POCl3 in pyridine.
- Specialized reagents and their acronyms: MCPBA= meta-chloroperbenzoic acid; HOAC = acetic acid, NaOAc = Sodium Acetate; Ph= phenyl = C6H5-; P(Ph)3 = triphenyl phosphine; NBS = N- bromosuccinimide, PBR3, SOCI2, AlCl3, FeBr3, H2SO4, Li, Na, Mg, Br2, CrO3, LDA = lithium diisopropylamide, PCC = pyridinium chlorochromate, KO-C(CH3)3, LAH = LIAIH4, (sia)2BH = disecondary isobutyl borane, KMNO4, HIO4 = periodic acid %3D %3D %3D %3D %3D write the missing reagents and solvents over the arrows. Some transformation require multiple steps. In some cases there will be multiple arrows. Br BrSpecialized reagents and their acronyms: MCPBA= meta-chloroperbenzoic acid; HOAC = acetic acid, NaOAc = Sodium Acetate; PhD phenyl = C6H5-; P(Ph)3 = triphenyl phosphine; NBS = N- bromosuccinimide, PBR3, SOCI2, AICI3, FeBr3, H2SO4, Li, Na, Mg, Brz2, CrO3, LDA = lithium diisopropylamide, PCC = pyridinium chlorochromate, KO-C(CH3)3, LAH = LIAIH4, (sia)2BH = disecondary isobutyl borane, KMNO4, HIO4 = periodic acid %3D %3D %3D %3D write the missing reagents and solvents over the arrows. Some transformation require multiple steps. In some cases there will be multiple arrows. -- -Li OH H- H.if the pKa value for p-nitrophenol is 7.08, what fraction of it exists in its ionized form at (a) pH 7, and (b) pH 9?
- Suppose you took your two compounds, dissolved them in tertbutyl methyl ether and then added them to a separatory funnel. Now suppose you add in aqueous sodium bicarbonate and vigorusly shake the contents of the separatory funnel. ethanol will be dissolved in tert butyl methyl ether ether and valeric acid will be dissolved in the aqueous sodium bicarbonate layer. Draw the EXACT chemical structure that will exist in each of the layers after shaking with sodium bicarbonate. (Is it neutral or charged?)You are given a mixture containing the three compounds shown below. Outline a procedure using a flow chart for the separation and isolation of all three compounds, using acid-base extractions. All three are solids at room temperature and are insoluble in deilonized water. You have access to all standard laboratory glassware and equipment, and the standard lab chemicals. .CO2H O,N. „NH2 HO2C napthalene terephthalic acid 3-nitroanilineLow-molecular-weight dicarboxylic acids normally exhibit two different pK, values. Ionization of the first carboxyl group is easier than the second. This effect diminishes with molecular size, and for adipic acid and longer chain dicarboxylic acids, the two acid ionization constants differ by about one pK unit. Dicarboxylic Acid Structural Formula pK,2 a1 Охalic НООССООН 1.23 4.19 Malonic НООСCH,COOH 2.83 5.69 Succinic HOOC(CH,),COOH 4.16 5.61 Glutaric HOOC(CH,),COOH 4.31 5.41 Adipic HOOC(CH,),COOH 4.43 5.41 Why do the two pK, values differ more for the shorter chain dicarboxylic acids than for the longer chain dicarboxylic acids?