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When a consumer purchases a tomato, smell is one of the factors affecting selection. Researchers in Japan have thus analyzed the volatile components of tomatoes using a novel method.11 Among the complex mixture of 367 compounds detected were 3-methylbutanal and hexanal. Propose a single synthesis that produces an equimolar mixture of these two compounds (equal amounts of both products) starting with one
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- Following is the structural formula of the tranquilizer meparfynol (Oblivon). Propose a synthesis for this compound starting with acetylene and a ketone. (Notice the -yn- and -ol in the chemical name of this compound, indicating that it contains alkyne and hydroxyl functional groups.)arrow_forwardA student attempted to prepare 1-chlorobutane by mixing 1-butanol with NaCl in acetone. Was the student succesful? Explain.arrow_forwardYou are given a mixture of benzoic acid, 2-naphthol and 1,4-dimethoxybenzene and you are asked to separate the mixture into its following compounds. You are limited to using dichloromethane, pentane, cyclohexane and ethyl acetate as organic solvents. This doesn't involve solvents used to convert the 3 compounds to ionic salts. Suggest possible organic solvents and explain a procedure you would carry out to separate the 3 mixtures briefly.arrow_forward
- Draw a diagram similar to that in figure 6 detailing the separation of 1,2-dichlorobenzene, phenol (pka = 10), and pyridine by an extraction protocol. OH aa CI 1,2-dichlorobenzene phenol ·N·. pyridinearrow_forwardPropose an efficient synthesis for two of the following target molecules, starting with any of the following starting materials for the source of carbon atoms: (i) benzene, (i) any alcohol containing four or fewer carbon atoms, (im) carbon dioxide, (iv) cyanide ion. This means that any carbon atom that ends up in the target molecule must come from one of these starting materials! Br (а) H2N (b) HOarrow_forwardThe fungus responsible for Dutch elm disease is spread by European bark beetles when they burrow into the tree. Other beetles congregate at the site, attracted by the scent of a mixture of chemicals, some emitted by other beetles and some coming from the tree. One of the compounds given off by female bark beetles is 4-methyl-3-heptanol. Suggest an efficient synthesis of this pheromone from alcohols of five carbon atoms or fewer.arrow_forward
- Predict the major organic product of the reaction sequence described. Styrene (1.53 g, 0.011 mol) in methanol (30 mL) was added to a mixture of Hg(OAc)2 (5.30 g, 0.016 mol) in methanol (100 mL) at room temp. and stirred for 24 hours. Sodium hydroxide (3.0 M, 16 mL) was added, followed by NaBH4 (0.32 g, 0.008 mol) in NaOH (3.0 M, 16 mL) at 0 °C. The precipitated Hg was removed by filtration. The product was isolated by diethyl ether extraction. After drying over Na2SO4, solvent was removed and distillation gave the productarrow_forwardIn the presence of excess base and excess halogen, a methyl ketone is converted to a carboxylate ion. The reaction is known as the haloform reaction because one of the products is haloform (chloroform, bromoform, or iodoform). Before spectroscopy became a routine analytical tool, the haloform reaction served as a test for methyl ketones: the formation of iodoform, a bright yellow compound, signaled that a methyl ketone was present. Why do only methyl ketones form a haloform?arrow_forwardThis is a multistep syntheses. More than one reagent/reaction will be necessary to produce the product. Provide all necessary reaction conditions (HBr, HgSO4, etc.) and the products produced after each step of the synthesis.arrow_forward
- ›Predict the major organic product of the reaction sequence described. Styrene (1.53 g, 0.011 mol) in methanol (30 mL) was added to a mixture of Hg(OAc)₂(5.30 g, 0.016 mol) in methanol (100 mL) at room temp. and stirred for 24 hours. Sodium hydroxide (3.0 M, 16 mL) was added, followed by NaBH (0.32 g, 0.008 mol) in NaOH (3.0 M, 16 mL) at 0 °C. The precipitated Hg was removed by filtration. The product was isolated by diethyl ether extraction. After drying over Na₂ SO4, solvent was removed and distillation gave the product. (Adapted from: Senda, Y.; Kanto, H.; Itoh, H. J. Chem. Soc., Perkin Trans. 2 1997, 1143–1146.) Draw the major organic product. H₂O Harrow_forwardFollowing is a retrosynthetic analysis for the synthesis of the herbicide (S)-Metolachlor from 2-ethyl-6-methylaniline, chloroacetic acid, acetone, and methanol. CI OMe OMe OMe 'N' HN N CI. + НО, Chloroacetic acid (S)-Metolachlor 3 NH2 CI + MEOH OMe Acetone Methanol 2-Ethyl-6-methylaniline Show reagents and experimental conditions for the synthesis of Metolachlor from these four organic starting materials. Your synthesis will most likely give a racemic mixture. The chiral catalyst used by Novartis for reduction in Step 2 gives 80% enantiomeric excess of the S enantiomer.arrow_forwardAlcohols are important for organic synthesis, especially in situations involving alkenes. The alcohol might be the desired product, or the OH group might be transformed into another functional group via halogenation, oxidation, or perhaps conversion to a sulfonic ester derivative. Formation of an alcohol from an alkene is particularly powerful because conditions can be chosen to produce either the Markovnikov or non-Markovnikov product from an unsymmetrical alkene. Using your reaction roadmap as a guide, show how to convert 4-methyl-1-pentene into 5-methylhexanenitrile. You must use 4-methyl-1-pentene and sodium cyanide as the source of all carbon atoms in the target molecule. Show all reagents needed and all molecules synthesized along the way.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning