Explain why the reaction of 2-bromopropane with NaOCOCH3 gives (CH3)2CHOCOCH3 exclusively as product, but the reactionof 2-bromopropane with NaOCH,CHg gives a mixture of (CH3)CHOCH,CHs (20%) and CH3CH=CH2 (80%).

The reason why reaction of 2-bromopropane with NaOCOCH3 forms CH32CHOCOCH3, whereas the reaction of…

Answered: Explain why the reaction of…

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter14: Conjugated Compounds And Ultraviolet Spectroscopy

Section14.SE: Something Extra

Problem 54AP

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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.
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.
Show how HC≡CH, CH3CH2Br, and (CH3)2CHCH2CH2Br can be used to prepare CH3CH2C≡CCH2CH2CH(CH3)2. Show all reagents, and use curved arrows to show movement of electron pairs.
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. d. Suggest a reagent to convert A to the single stereoisomer X.
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Explain why the reaction of 2-bromopropane with NaOCOCH3 gives (CH3)2CHOCOCH3 exclusively as product, but the reaction of 2-bromopropane with NaOCH,CHg gives a mixture of (CH3)CHOCH,CHs (20%) and CH3CH=CH2 (80%).