Concept explainers
Interpretation:
The absolute configuration at the chirality center in the
Concept introduction:
The dihydroxylation is the addition of two hydroxyl groups to the double bond of an
The dihydroxylation of alkene is a
The osmium tetroxide reacts with alkene and forms a cyclic osmate ester. In the presence of an oxidizing agent, this ester forms a diol.
The stereochemistry of chiral center is predicted by assigning the absolute configuration to the molecule.
The absolute conjugation can be determined by assigning priority to the groups bonded to chirality center.
The priority order is decided by Cahn-Ingold-Prelog priority rules. If the order of priority of groups bonded to chirality center preceding
The
The
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ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
- When a 2, 6-disubstituted allyl phenyl ether is heated in an attempted Claisen rearrangement, migration occurs to give the p-allyl product as the result of two sequential pericyclic reactions. Explain.arrow_forwardIn addition to organic halides, alkyl tosylates (R'OTs. Section 9.13) also react with organocuprates (R2CuLi) to form coupling products R – R'. When 2° alkyl tosylatee are used as starting materials (R2CHOTs), inversion of the configuration at a stereogenic center results. Keeping this in mind, draw the product formed when each compound is treated with (CH3)2CuLi.arrow_forwardDraw the substitution product formed (including stereochemistry) when (R)-hexan-2-ol is treated with each series of reagents: (a) NaH, followed by CH3I; (b) TsCl and pyridine, followed by NaOCH3; (c) PBr3, followed by NaOCH3. Which two routes produce identical products?arrow_forward
- (a) Which diastereomer of oct-4-ene yields a mixture of two enantiomers, (4R,5R)- and (4S, 5S)-4,5-dibromooctane on reaction with Br2? (b) Which diastereomer of oct-4-ene yields a single meso compound, (4R, 5S)-4,5-dibromooctane?arrow_forwardComplete the three following SN1 reactions by drawing the structure of the major product(s). If the product is a mixture of stereoisomers, draw all possibilities and indicate their relationship (i.e. enantiomers or diastereomers).arrow_forwardIn addition to organic halides, alkyl tosylates (R'OTs. Section 9.13) also react with organocuprates (R2CuLi) to form coupling products R – R'. When 2° alkyl tosylatee are used as starting materials (R2CHOTs), inversion of the conguration at a stereogenic center results. Keeping this in mind, draw the product formed when each compound is treated with (CH3)2CuLi.arrow_forward
- Draw the major product formed when HBr reacts with the following epoxide. Use wedge/dash bonds, including H's at each stereogenic center, to show the stereochemistry of the product.arrow_forwardIn addition to organic halides, alkyl tosylates react with organocuprates (R2CuLi) to form coupling products R–R′. When 2° alkyl tosylates are used as starting materials (R2CHOTs), inversion of the configuration at a stereogenic center results. Keeping this in mind, draw the product formed when each compound is treated with (CH3)2CuLi.arrow_forwardSteps 5 and 6 combined are best described as which of the following? 1. A reduction followed by reoxidation at C3 2. Two keto-enol tautomerizations that lead to stereochemical inversion at C3 3. An elimination followed by addition that leads to stereochemical retention at C4 4. Dehydration followed by hydration that leads to stereochemical retention at C4arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning