Concept explainers
Interpretation:
The reagents to bring about the synthesis of the given compound from cyclohexane have to be shown.
Concept Introduction:
Retrosynthesis: The synthesizing a target molecule a synthetic route must be designed to give a pure sample of the target molecule using a convenient and efficient method.
A logical approach for designing
Grignard reagent: Alkyl or aryl magnesium halides (
Synthesis of Grignard reagent is shown below,
Acid Catalyzed Hydration Reaction: The reaction involves breaking of π-bonds between carbon-carbon multiple bonds and addition of alcohol to more substituted position of carbon in the molecule.
Nucleophiles: A nucleophile is a more reactant species that affords a pair of electrons to the electrophile or electrophilic center and forms a new covalent bond. The carbon or other hetero atom in a molecule which is bearing negative charge or lone pair of electron is called as nucleophiles.
Ring-opening of
Stereoisomers are isomeric molecules that have the same molecular formula and sequence of bonded atoms but differ in the three-dimensional orientations of their atoms in space.
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Chapter 15 Solutions
Organic Chemistry
- Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forwardHow would you perform an experiment to produce cyclohexanol from cyclohexene? Describe in detail the reagents and glassware you would use including approximate amounts and concentrations of reagents. What steps would be needed to purify the cyclohexanol from the other reagents used in the reaction?arrow_forwardDraw out the reaction mechanism for cyclohexanol to cyclohexanone. Sodium hypochlorite oxidation of an alcohol to a ketone with the product being cyclohexanone.arrow_forward
- Acetylene reacts with sodium amide in the presence of propyl halide produces aldehyde produces ketones It produces 2-pentanearrow_forwardPropose a mechanism for the acid-catalyzed hydration of 1-methylcyclohexene to give 1-methylcyclohexanol. Which step in your mechanism is rate-determining?arrow_forwardA dialkyl-substituted benzene, C14H22, is treated with basic potassium permanganate, followed by acid workup. The same dialkyl-substituted benzene was recovered afterward from the reaction mixture. Draw the structure of the compound.arrow_forward
- Propose a mechanism for the acid-catalyzed hydration of methylidenecyclohexane to give 1-methylcyclohexanol. Which step in your mechanism is rate-determining?arrow_forwardEthylene oxide is the starting material for the synthesis of 1,4-dioxane. Propose a mechanism for each step in this synthesis.arrow_forwardAldehydes and ketones react with thiols to yield thioacetals just as they react with alcohols to yield acetals. Predict the product of the following reaction, and propose a mechanism:arrow_forward
- Using your reaction roadmap as a guide, show how to convert butane into butanal. Show all reagents needed and all molecules synthesized along the way.arrow_forwardClaisen condensation between diethyl phthalate and ethyl acetate followed by saponification, acidification, and decarboxylation forms a diketone, C9H6O2. Propose structural formulas for compounds A and B and the diketone.arrow_forwardFollowing 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_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning