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
- Following is a retrosynthetic analysis for an intermediate in the industrial synthesis of vitamin A. (a) Addition of one mole of HCl to isoprene gives 4-chloro-2-methyl-2-butene as the major product. Propose a mechanism for this addition and account for its regioselectivity. (b) Propose a synthesis of the vitamin A precursor from this allylic chloride and ethyl acetoacetate.arrow_forwardTreating 2-methylpropene with methanol in the presence of sulfuric acid gives tert-butyl methyl ether Propose a mechanism for the formation of this ether.arrow_forwardPropose a mechanism for the acid-catalyzed reaction of cyclohexanone with ethylene glycol to give cyclohexanone ethylene acetal.arrow_forward
- Provide reaction mechanisms for the following transformationsarrow_forwardPropose a mechanism for the reaction of 1-methylcyclohexanol with HBr to form 1-bromo-1-methylcyclohexanearrow_forwardShow you would use Grignard syntheses to prepare the following alcohols from the indicated starting materials and anyother necessary reagents. 1-cyclohexylethanol from acetaldehyde, CH3CHOarrow_forward
- Treatment of 3-chloro-2-cyclohexenone with sodium ethoxide in methanol gives 3-ethoxy-2-cyclohexene. Propose a mechanism for this reaction that accounts for the formation of the product.arrow_forwardShow how to synthesize 3-nitro-4-propoxybenzoic acid from phenol, C6H5OH and any reagents that you need.arrow_forwardProvide reagents needed to bring about the following transformation.arrow_forward
- How 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_forwardSyntheses of each of the following compounds have been reported in the chemical literature. Using the indicated starting material and any necessary organic or inorganic reagents, describe short sequences of reactions that would be appropriate for each transformation. (a) 1,1,5-Trimethylcyclononane from 5,5-dimethylcyclononanonearrow_forwardShow the products from the reaction of p-bromoaniline with following reagents: a)CH3Cl(excess) b) HCl c) CH3COCl d) CH3MgBr e) CH3CH2Cl, AlCl3arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningEBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT