Interpretation:
The two syntheses with different approaches are to be devised for
Concept introduction:
Terminal
(Z)-Alkenes on reaction with either osmium tetroxide or with cold dilute potassium permanganate, give syn esters and then produce syn
(E)-Alkenes on reaction with meta-chloroperbenzoic acid give
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Organic Chemistry
- The following sequence of steps converts (R)-2-octanol to (S)-2-octanol. Propose structural formulas for intermediates A and B, specify the configuration of each, and account for the inversion of configuration in this sequence.arrow_forwardWhen exactly 1 mole of methane is mixed with exactly 1 mole of chlorine and light is shone on the mixture, a chlorination reaction occurs. The products are found to contain substantial amounts of di-, tri-, and tetrachloromethane, as well as unreacted methane. Explain how a mixture is formed from this stoichiometric mixture of reactants, and propose mechanisms for the formation of these compounds from chloromethane.arrow_forwardHydroboration of the following bicycloalkene followed by oxidation in alkaline hydroperoxide is both stereoselective and regioselective. The product is a single alcohol in better than 95% yield.Propose a structural formula for this alcohol and account for the stereo- and regio- selectivity of its formation. Hint: Examine a molecular model of this alkene and see if you can determine which face of the double bond is more accessible to hydroboration.arrow_forward
- Two substitution products result from the reaction between 3-chloro-3-methyl-1- butene with sodium acetate (CH3COO – Na +) in acetic acid under SN1. Identify the products.arrow_forwardThe compound below is treated with chlorine in the presence of light. CH3 CH3CHCH,CH3 Draw the structure for the organic radical species produced by reaction of the compound with a chlorine atom. Assume reaction occurs at the weakest C-H bond. • You do not have to consider stereochemistry. You do not have to explicitly draw H atoms.arrow_forwardThe major product of the following reaction exists as two stereoisomers. Draw both isomers: show all hydrogen atoms in the structures. Use wedge and dash bonds to indicate the stereochemistry (you don’t need to draw wedge and dash bonds for C-H bonds of CH3 and CH2 groups). Assign stereo configuration of the asymmetric carbon atoms and write the relationship between two isomers.arrow_forward
- Addition of HBr to 3,3-dimethyl-1-butene gives a mixture of two isomeric alkyl bromide products. Please daw structures for the two products, and give a mechanistic explanation for their formation.arrow_forwardМЕСНANISMS 1,2-epoxy-1-methylcyclopentane undergoes both acid-catalyzed and base-catalyzed opening of the epoxide ring to form two different products. > Using ethanol as the solvent and an appropriate acid, show the steps in the acid catalyzed mechanism, writing structures for all products of the steps. Circle the major product(s). > Using ethanol as the solvent and an appropriate base, show the steps in the base- catalyzed mechanism, writing structures for all products of the steps. Circle the major product(s). 1,2-epoxy-1-methylcyclopentane CH3arrow_forwardDraw an approximate reaction-energy diagram showing the curves for the two possible pathways for ionic addition of HBr to 1-methylcyclohexene. (a) Formation of the major product, 1-bromo-1-methylcyclohexane, and (b) formation of the minor product, 1-bromo-2-methylcyclohexane. Point out how these curves show that 1-bromo-1-methylcyclohexane should be formed fasterarrow_forward
- Draw a structural formula of an alkene or alkenes (if more than one) that undergo acid-catalyzed hydration and without rearrangement give 2-methyl-2-butanol as the MAJOR product. You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. If more than one structure fits the description, draw them all. Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures with + signs from the drop-down menu.arrow_forwardEthers can be prepared by reaction of an alkoxide or phenoxide ion with a primary alkyl halide. Draw the structure of the expected organic product of the reaction of 1-iodo-2-methylpropane with the following alkoxide ic + O Na You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • Do not include counter-ions, e.g., Na", I", in your answer. C opy astearrow_forwardAlcohols are acidic in nature. Therefore, a strong base can abstract the acidic hydrogen atom of the alcohol in a process known as deprotonation. The alcohol forms an alkoxide ion by losing the proton attached to the oxygen atom of the hydroxyl ( -OH) group. The alkoxide formed can act as a base or a nucleophile depending on the substrate and reaction conditions. However, not all bases can abstract the acidic proton of alcohols and not all alcohols easily lose the proton. Deprotonation depends on the strength of the base and the acidity of the alcohol. Strong bases, such as NaNH2, can easily abstract a proton from almost all alcohols. Likewise, more acidic alcohols lose a proton more easily. Determine which of the following reactions would undergo deprotonation based on the strength of the base and the acidity of the alcohol. Check all that apply. ► View Available Hint(s) CH3CH,OH + NH3 →CH,CH,O-NH CH3 CH3 H3C-C-H+NH3 → H3 C-C-H OH O-NH CH3CH2OH + NaNH, → CH3CH,O-Na* + NH3 CHC12 Cl₂…arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning