(R)-2-butanol reacts with phosphorus tribromide to give A (C4H9Br). Treatment of A with sodium cyanide in DMF gives B (C5H9)N. B is opticallyactive. Draw the structure of B.• Use the wedge/hash bond tools to indicate stereochemistry where it exists.Show stereochemistry in a meso compound.Sn [F?ChemDoodleⓇ Cyclohexene reacts with m-chloroperoxybenzoic acid to give A (C6H100). A reacts with methylmagnesium iodide in anhydrous ether to give B(C7H₁40). Draw the structure of B.O• Use the wedge/hash bond tools to indicate stereochemistry where it exists.Show stereochemistry in a meso compound.If the reaction produces a racemic mixture, draw both stereoisomers.●• Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner.Separate multiple products using the + sign from the drop-down menu.?ChemDoodleⓇSn [F

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(R)-2-butanol reacts with phosphorus tribromide to give A (C4H9Br). Treatment of A with sodium cyanide in DMF gives B (C5H9)N. B is optically active. Draw the structure of B. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Show stereochemistry in a meso compound. 90-85 To th OO. [F

(R)-2-butanol reacts with phosphorus tribromide to give A (C4H9Br). Treatment of A with sodium cyanide in DMF gives B (C5H9)N. B is optically active. Draw the structure of B. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Show stereochemistry in a meso compound. 90-85 To th OO. [F

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter5: Stereochemistry At Tetrahedral Centers

Section5.SE: Something Extra

Problem 70AP

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A difficult problem in the synthesis of PGF2α is the introduction of the OH group at C15 in the desired conguration.a. Label this stereogenic center as R or S.b. A well known synthesis of PGF2α involves reaction of A with Zn(BH4)2, a metal hydride reagent similar in reactivity to NaBH4, to form two isomeric products, B and C. Draw their structures and indicate their stereochemical relationship.c. Suggest a reagent to convert A to the single stereoisomer X.
A difficult problem in the synthesis of PGF2α is the introduction of the OH group at C15 in the desired configuration. a. Label this stereogenic center as R or S. b. A well known synthesis of PGF2α involves reaction of A with Zn(BH4)2, a metal hydride reagent similar in reactivity to NaBH4, to form two isomeric products, B and C. Draw their structures and indicate their stereochemical relationship. c. Suggest a reagent to convert A to the single stereoisomer X.
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draw the two possible carbocations that can form when this alkene reacts with a strong acid (such as HBr or H3O+). of the two structures you drew, circle the more stable carbocation
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