Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 23.SE, Problem 33MP
Azlactones are important starting materials used in the synthesis of dehydro α-aminoacids. They react with
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α-Amino acids can be prepared by treating an aldehyde with ammonia/trace acid, followed by hydrogen cyanide, followed by acid-catalyzed hydrolysis.
Draw the structures of the two intermediates formed in this reaction.
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NaBH₂CN,
EtOH, pH= 4
Using the data in Appendix C, determine which of the following bases is strong enough to deprotonate acetonitrile (CH3CN), so that equilibrium favors the products: (a) NaH; (b) Na2CO3; (c) NaOH; (d) NaNH2; (e) NaHCO3.
Chapter 23 Solutions
Organic Chemistry
Ch. 23.1 - Prob. 1PCh. 23.1 - Prob. 2PCh. 23.3 - Prob. 3PCh. 23.3 - Prob. 4PCh. 23.4 - Prob. 5PCh. 23.4 - 1-Butanol is prepared commercially by a route that...Ch. 23.4 - Prob. 7PCh. 23.5 - Prob. 8PCh. 23.6 - Prob. 9PCh. 23.6 - What product would you Expect to obtain from base...
Ch. 23.7 - Show the products you would expect to obtain by...Ch. 23.7 - Prob. 12PCh. 23.8 - What product would you expect from the following...Ch. 23.9 - What product would you expect From the following...Ch. 23.9 - Prob. 15PCh. 23.10 - Prob. 16PCh. 23.10 - Prob. 17PCh. 23.10 - Prob. 18PCh. 23.11 - Prob. 19PCh. 23.11 - Show how you might use an enamine reaction to...Ch. 23.12 - Prob. 21PCh. 23.12 - How would you prepare the following compound using...Ch. 23.SE - Prob. 23VCCh. 23.SE - Prob. 24VCCh. 23.SE - Prob. 25VCCh. 23.SE - The following molecule was formed by a Robinson...Ch. 23.SE - Prob. 27MPCh. 23.SE - Prob. 28MPCh. 23.SE - Predict the product(s) and provide the mechanism...Ch. 23.SE - Predict the product(s) and provide the mechanism...Ch. 23.SE - Predict the product(s) and provide the mechanism...Ch. 23.SE - Knoevenagel condensation is a reaction involving...Ch. 23.SE - Azlactones are important starting materials used...Ch. 23.SE - Prob. 34MPCh. 23.SE - Isoleucine, another of the twenty amino acids...Ch. 23.SE - The first step in the citric acid cycle of food...Ch. 23.SE - Prob. 37MPCh. 23.SE - The Knoevenagel reaction is a carbonyl...Ch. 23.SE - The Darzens reaction invoIves a two-step,...Ch. 23.SE - The following reaction involves a hydrolysis...Ch. 23.SE - Prob. 41MPCh. 23.SE - Prob. 42MPCh. 23.SE - Prob. 43MPCh. 23.SE - Propose a mechanism for the following...Ch. 23.SE - Prob. 45MPCh. 23.SE - Prob. 46MPCh. 23.SE - Prob. 47MPCh. 23.SE - Prob. 48APCh. 23.SE - Prob. 49APCh. 23.SE - Prob. 50APCh. 23.SE - Prob. 51APCh. 23.SE - Prob. 52APCh. 23.SE - Prob. 53APCh. 23.SE - Prob. 54APCh. 23.SE - Prob. 55APCh. 23.SE - Prob. 56APCh. 23.SE - Prob. 57APCh. 23.SE - Prob. 58APCh. 23.SE - In the mixed Claisen reaction of cyclopentanone...Ch. 23.SE - Ethyl dimethylacetoacetate reacts instantly at...Ch. 23.SE - Prob. 61APCh. 23.SE - Prob. 62APCh. 23.SE - The so-called Wieland-Miescher ketone is a...Ch. 23.SE - Prob. 64APCh. 23.SE - Prob. 65APCh. 23.SE - Prob. 66APCh. 23.SE - What condensation products would you expect to...Ch. 23.SE - The following reactions are unlikely to provide...Ch. 23.SE - Fill in the missing reagents a-h in the following...Ch. 23.SE - Prob. 70APCh. 23.SE - Prob. 71APCh. 23.SE - Prob. 72APCh. 23.SE - Prob. 73AP
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- Q4:- Draw structures, give names, and classify as primary, secondary, or tertiary amine : the eight isomeric amines of formula CaHi.N Q5:- Give structures and names of the principal organic reactants and products of the following reactions. a- conversion of Carboxylic Acids into Esters b- Hydrolysis of nitrites. c- Hofmann degradation of amides Q6:- Arrange the compounds of each set in order of basicity ? Explain your choice. ethylamine, 2-aminoethanol, 3-amino-l-propanolarrow_forwardPrepare CH3COOC2H5, ethyl acetate, using ethyl alcohol. Write the chemical reaction. The pain reliever acetaminophen is produced by reacting 4-aminophenol with acetic anhydride. Outline a synthesis of acetaminophen from 4-aminophenol including any needed inorganic reagents.arrow_forwardDraw structural formulas for the following compounds: (a) Tributylamine(b) N-methylanilinium chloride(c) ethylammonium chloride (d) 2-amino-1-pentanol(e) 3,3-dimethyl-N-phenyl-2-aminohexane (f) 1,2-ethanediaminearrow_forward
- (a) Compound Z is a tertiary aromatic amine with the formula, C8H11N. Provide a chemical structure for compound Z. (b)nDraw the structure of the product formed exclusively when nitrous acid reacts with Z.arrow_forward1 Aromatic amines can be made from reacting benzene in the presence of concentrated nitric and sulfuric acid. a State the electrophile in the first stage of this reaction. b State the conditions required to reduce the nitro group to an amine group. c Draw the skeletal formula and state the name of the amine product of this two-stage reaction.arrow_forward(a) Predict the product of the reaction of KOH with 1-amino propane. (b) Predict the product of a deprotonated ethanol (an “ethanolate anion", O-CH2-CH3) with phenol (hydroxybenzene). (c) Predict the product of propanoic acid with deprotonated ethanol (an “ethanolate anion", O-CH2-CH3).arrow_forward
- An aqueous solution of a primary or secondary amine reacts with an acyl chloride to form an amide as the major product. However, if the amine is tertiary, an amide is not formed. What product is formed? Explain.arrow_forwardNote these acronyms: HOAC = Acetic Acid; NaOAc = Sodium Acetate; THF = tetrahydrofuran Ph = Phenyl = C6H5; DMSO = Dimethyl Sulfoxide, H3C-O-H = methanol, NBS = N-Bromo succinimide, LDA = Lithium Diisopropylamide, DIA = Diisopropyl Amine, ACN=Acetonitrile Acetone = Acetic Acid = THF= DMSO= Ph= H3C `CH3 HạC HO, H3C CH3 2. Write the major alkene product formed when the bromides below react with the specified base. NaOH, DMSO solvent LDA, THF solvent 3. Will the reaction conditions below favor SN2 or E2 chemistry? Simply write SN2 or E2 on the right side of the arrow). a) Br LDA, THF solventarrow_forwardNote these acronyms: HOAC = Acetic Acid; NaOAc = Sodium Acetate; THF = tetrahydrofuran Ph = Phenyl = C6H5; DMSO = Dimethyl Sulfoxide, H3C-O-H = methanol, NBS = N-Bromo succinimide, LDA = Lithium Diisopropylamide, DIA = Diisopropyl Amine, ACN=Acetonitrile Acetone = Acetic Acid = THF= DMSO= Ph= H3C CH3 H3C HO. H3C CH3 1. Circle the bromide below that most rapidly undergoes E2 reaction with NaOH in DMSO. The R group is tertiary butyl. Use conformational analysis to explain your answer. 2. Write the major alkene product formed when the bromides below react with the specified base. NaOH, DMSO solvent -Br -Ph Br NaOH, DMSO solvent Pharrow_forward
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