Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Textbook Question
Chapter 20, Problem 14PP
Practice Problem 20.14
Outline a synthesis of orange a from 2-naphthol and p-aminobenzenesulfonic acid.
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Devise a synthesis of benzocaine, ethyl p-aminobenzoate (H2NC6H4CO2CH2CH3), from benzene, organic alcohols, and any needed organic or inorganic reagents. Benzocaine is the active ingredient in the topical anesthetic Orajel (Section 18.15C).
19.57 Because phenol (C6H5OH) is less acidic than a carboxylic acid, it can be
deprotonated by NaOH but not by the weaker base NaHCO3. Using this
information, write out an extraction sequence that can be used to
separate C6H5OH, benzoic acid, and cyclohexanol. Show what
compound is present in each layer at each stage of the process, and if it
is present in its neutral or ionic form.
Devise a synthesis of benzocaine, ethyl p-aminobenzoate (H2NC6H4CO2CH2CH3), from benzene, organic alcohols, and any needed organic or inorganic reagents. Benzocaine is the active ingredient in the topical anesthetic Orajel.
Chapter 20 Solutions
Organic Chemistry
Ch. 20 - Prob. 1PPCh. 20 - Prob. 2PPCh. 20 - Practice Problem 20.3
Write a mechanism that...Ch. 20 - Prob. 4PPCh. 20 - PRACTICE PROBLEM 20.5 Outline a preparation of...Ch. 20 - Prob. 6PPCh. 20 - Prob. 7PPCh. 20 - Prob. 8PPCh. 20 - Prob. 9PPCh. 20 - Prob. 10PP
Ch. 20 - Practice Problem 20.11 In the preceding examples...Ch. 20 - Prob. 12PPCh. 20 - Prob. 13PPCh. 20 - Practice Problem 20.14
Outline a synthesis of...Ch. 20 - Prob. 15PPCh. 20 - Prob. 16PPCh. 20 - Prob. 17PPCh. 20 - Prob. 18PPCh. 20 - Prob. 19PCh. 20 - 20.20 Give common or systematic names for each of...Ch. 20 - Which is the most basic nitrogen in each compound?...Ch. 20 - Prob. 22PCh. 20 - Prob. 23PCh. 20 - Show how you might synthesize each of the...Ch. 20 - Prob. 25PCh. 20 - 20.26 Provide the major organic product from each...Ch. 20 - Prob. 27PCh. 20 - 20.28 What products would you expect to be formed...Ch. 20 - Prob. 29PCh. 20 - Prob. 30PCh. 20 - Prob. 31PCh. 20 - Write equations for simple chemical rests or state...Ch. 20 - Prob. 33PCh. 20 - Explain the following, including mention of key...Ch. 20 - 20.35 Provide a detailed mechanism for each of the...Ch. 20 - Prob. 36PCh. 20 - Prob. 37PCh. 20 - Prob. 38PCh. 20 - Prob. 39PCh. 20 - 20.40 Give structures for compounds R-W:
Ch. 20 - Prob. 41PCh. 20 - Prob. 42PCh. 20 - Diethylpropion (shown here) is a compound used in...Ch. 20 - Prob. 44PCh. 20 - 20.45 Compound W is soluble in dilute aqueous HCI...Ch. 20 - 20.46 Propose structures for compounds X, Y, and...Ch. 20 - Compound A(C10H15N) is soluble in dilute HCI. The...Ch. 20 - Prob. 48PCh. 20 - Prob. 49PCh. 20 - For each of the following, identify the product...Ch. 20 - 20.51 Develop a synthesis for the following...Ch. 20 - 20.52 When phenyl isochiocyanatc, , is reduced...Ch. 20 - Prob. 53PCh. 20 - 20.54 Propose a mechanism that can explain the...Ch. 20 - When acetone is treated with anhydrous ammonia in...Ch. 20 - Prob. 56P
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- Synthesize ethylbenzoate using benzoic acid and acetonitrile.arrow_forward19.48 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. OH OH phthalic acid pKa1 = 2.9 pKa2 = 5.4 HO isophthalic acid pkat = 3.7 PK a2 = 4.6 pKa2 Draw out the single anions (one deprotonation) and bear in mind that there is free rotation about C-C single bonds. OH Look for stabilization based on the conformations possible from Such rotation.arrow_forwardHN 21.10 Suggest reagents. HNarrow_forward
- 22.47 Tertiary amines with three different alkyl groups are chiral but cannot be resolved because pyramidal inversion causes racemization at room temperature. Nevertheless, chiral aziridines can be resolved and stored at room temperature. Aziridine is a three-membered heterocycle containing a nitrogen atom. The following is an example of a chiral aziridine. In this compound, the nitrogen atom is a chiral center. Suggest a reason why chiral aziridines do not undergo racemization at room temperature.arrow_forward18arrow_forwardGive reasons :(a) Aniline is a weaker base than cyclohexyl amine.(b) It is difficult to prepare pure amines by ammonolysis of alkyl halides.arrow_forward
- Show how to convert amines to other functional groups, and devise multistepsyntheses using amines as starting materials and intermediatesarrow_forwardDevise a synthesis of benzocaine, ethyl p-aminobenzoate(H2NC6H4CO2CH2CH3), from benzene, organic alcohols, and any neededorganic or inorganic reagents. Benzocaine is the active ingredient in thetopical anesthetic Orajelarrow_forward19 & 20. 19. 20. Consider the following synthetic estrogen shown below O= H Im Compound X The maximum number of stereoisomers in X is Illllllll CH3 a OH CH3 Draw compound X below and prioritize the groups present in the stereocenter labeled as a.arrow_forward
- Synthesize octadecyl stearate using linoleic acid (18:2) (Given, stearic acid: 18:0) as the only starting material.arrow_forwardAs 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?arrow_forwardIn the mid-1930s a substance was isolated from a fungus that is a parasite of ryes and other grasses. This alkaloid, lysergic acid, has been of great interest to chemists because of its strange, dramatic action on the human mind. Many derivatives of lysergic acid are known, some with medicinal applications. Perhaps the best known derivative of lysergic acid is the potent hallucinogen lysergic acid diethylamide (LSD): మగవా జి N-H LSD (CH25N;O) Like other alkaloids, LSD is a weak base, with Kp = 7.6 × 107. What is the pH of a 0.94 M solution of LSD? pH =arrow_forward
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