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 CHEM. VOL.1+2-W/WILEYPLUS
- 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_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_forwardOptically active (R)-2-bromobutane can be converted to 2-butanol under either conditions A or conditions B. Describe the stereochemistry of the product solutions for the two different conditions.arrow_forward
- The 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_forwardDraw the line-angle formula of the enol formed in the following alkyne hydration reaction and then draw the structural formula of the carbonyl compound with which this enol is in equilibrium. -C=CH 1. (sia)2BH 2. NaOH/H₂O₂ an enol carbonyl compound • You do not have to consider stereochemistry. • Draw both the enol and the carbonyl forms. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures using the sign from the drop-down menu. ChemDoodleⓇ <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
- Name (including E/Z stereochemistry) the five alkenes that can produce 3-bromo-3-methylhexane on reaction with HBr. Draw the skeletal structure of each molecule.arrow_forwardThe reaction of 1-iodopropane with potassium thiocyanate (KSCN) in certain solvents results in the formation of two isomeric products, propylthiocyanate and propylisothiocyanate (see scheme below), via the SN2 reaction mechanism. Attempts to prepare a similar mixture of these same isomeric products (propylthiocyanate and propylisothiocyanate) starting from 1-propene is illustrated below. Despite the strong acidity of thiocyanic acid (recall pKa = 1.1), this addition reaction does not lead to either of the products indicated. Based on your knowledge of alkene addition reactions, explain this experimental result.arrow_forwardThe nitro groups on the benzene ring in the reactant serve two purposes.One is to let you know what atoms in the reactant correspond to what atomsin the product. But what role do the nitro groups play electronically – whywould the reaction be much slower if these nitro groups weren’t attached tothose benzene carbons? Draw any relevant structures to support youranswer.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning