Propose an efficient synthesis for the following transformation. x- f The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. A B Br2 D HBr G 1) 03; 2) DMS HBr, ROOR E H₂, Pd H 1) xs NaNH2, 2) H,O C cat. OsO4, NMO F H₂SO4, H₂O, HgSO4 1) R₂BH; 2) H₂O2, NaOH

Propose an efficient synthesis for the following transformation. x- f The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. A B Br2 D HBr G 1) 03; 2) DMS HBr, ROOR E H₂, Pd H 1) xs NaNH2, 2) H,O C cat. OsO4, NMO F H₂SO4, H₂O, HgSO4 1) R₂BH; 2) H₂O2, NaOH

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter19: Enolate Anions And Enamines

Section19.9: Crossed Enolate Reactions Using Lda

Problem EQ

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In this study, the researcher compared S N 2 and E2reaction rates for four substrates. Three of the substrates had a second halogen on the bposition in the molecule. This work also compared the behavior of two nucleophiles:dianion I and II. You should read the abstract and look at Scheme 1 (p. 3082) and Table 4(p. 3086). Abstract: The gas-phase reactions of benzoate and phenolate containing dianions with a series of ‚-substitutedalkyl bromides (X-CH2CH2Br, X ) H, F, Cl, Br) have been studied in a quadrupole ion trap mass spectrometer.Branching ratios between SN 2 and E2 products were measured and rate constants were determined. The‚-halogens increase both the S N 2 and E2 rates, but the effect is greater for the latter process and thereforethese substituents lead to an increase in the amount of elimination. The kinetic data for the SN 2 reactions canbe analyzed via a two-parameter, linear free-energy relationship and the results indicate that field-effects (i.e.,electron-withdrawing…
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