Concept explainers
Interpretation:
The synthesis for the given products is to be outlined by using benzene, toluene or aniline and any other required.
Concept introduction:
Bromination of
Grignard reagents are nucleophiles which are highly reactive, they can be obtained by reacting magnesium in diethyl ether with an alkyl or aryl bromide.
Swern oxidation of alcohols allows conversion of primary or secondary alcohols to an
Synthesis of β-hydroxyketone is possible by reacting an enolate with a carbonyl compound. Thus, various reagents can be used to convert a
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Organic Chemistry
- Isoerythrogenic acid, C18H26O2, is an acetylic fatty acid that turns a vivid blue on exposure to UV light. On Catalytic hydrogenation over a palladium catalyst, five molar equivalents of hydrogen are absorbed, and stearic acid, CH3(CH2)16CO2H, is produced. Ozonolysis of isoerythrogenic acid yields the following products: formaldehyde, CH2O, malonic acid, HO2CCH2CO2H, adipic acid, HO2C(CH2)4CO2H, and the aldehyde carboxylic acid, OHC(CH2)6CO2H. Provide a structure for isoerythrogenic acid.arrow_forwardChemistry Suggest a synthesis for the following compound from the indicated starting materials and any other necessary organic and inorganic materials: fromarrow_forwardStarting with benzene and using any other necessary reagents of your choice, what are the possible syntheses for the following compound?arrow_forward
- Propose a synthesis of the anti-inflammatory drug Ibuprofen from benzene. Show all reagents and all intermediate structures. Assume that ortho and para isomers can be separatedarrow_forwardQuinolines, heterocyclic compounds that contain a pyridine ring fused to a benzene ring, are commonly synthesized by a method known as the Skraupsynthesis, in which aniline reacts with glycerol under acidic conditions. Nitrobenzene is added to the reaction mixture to serve as an oxidizing agent.The first step in the synthesis is the dehydration of glycerol to propenal. a. What product would be obtained if para-ethylaniline were used instead of aniline?b. What product would be obtained if 3-hexen-2-one were used instead of glycerol?c. What starting materials are needed for the synthesis of 2,7-diethyl-3-methylquinoline?arrow_forwardGrignard reagent is a versatile tool in synthetic organic chemistry. Using bromocyclopentane as a starting material, show how a Grignard reagent, X, is synthesized. Reaction of X with water produces compound Y while treatment in carbon dioxide followed by hydrolysis forms compound Z. 3-methyl-2butanone reacts with X and hydrolyses to yield compound AA. Draw the structural formulae of compounds Y, Z and AA and write the chemical equations respectively.arrow_forward
- Discovery of the antibiotic sulphanilamide led to rapid development of a large number of structurally related sulphonamides. Some of these were useful leads to compounds with other medicinal properties. Amongst these, sulfasalazine was active in the treatment of ulcerative colitis, a potentially fatal disease of the colon. As a medicinal chemist, you are about to carry out the synthesis of sulfasalazine, starting from aniline. Give the chemical names and draw the chemical structures of the reagents you will need to use for the all the steps marked (a)-(d). Aniline HO₂C HO (a) N=N- ACHN Ac represents CH3CO Sulfasalazine SO,NH S0,C1 N (b) (d) H₂N- SO,NH (c) N [Oro] SO,NH N Step (a) in question 5 above results in the para product only. Explain why this occurs.arrow_forwardMyristoleic acid, C14H26O2, yields myristic acid on catalytic hydrogenation and undergoes oxidative cleavage with ozone to yield pentanoic acid and nonanedioic acid. Draw the structure of Myristoleic acid.arrow_forward2b)Synthesize the following from benzene or toluene, and/or small alcohols, using formaldehyde or ethylene oxide if needed:arrow_forward
- Cadaverine (1,5-diaminopentane) and putrescine (1,4-diaminobutane) are two compounds that are formed by bacterialaction and are responsible for the odor of rotting flesh. Drawtheir structures. Suggest a series of reactions to synthesize pu-trescine from 1,2-dibromoethane and any inorganic reagentsarrow_forwardCarototoxin is a natural pesticide produced by carrots, with formula C₁H2O. It undergoes hydrogenation with Pd to: give product A, C,H,O, and with Lindlar's catalyst to give product B, C,H2O. Ozonolysis followed by zinc leads to a mixture of methanal, octanal, 1,2-ethanedioic acid, 3-oxopropanoic acid, and 2-hydroxy-3-oxopropanoic acid. Draw possible structures for carototoxin, A, and B. Product B structure H2, Lindlar's Structure of carototoxin H2, Pd/C Product A structurearrow_forwardSuggest the starting reagent in the following reaction:arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning