8. Organometallic reagents, such as organolithium (RLi), Gilman or Organo-cuprates (R2)CuLi) and Grignard (R MgBr), have been known to transform ketones and aldehyde molecules. Pages 1032-1033 show these reagents can modify acid chlorides, acid anhydrides and esters. OR Given the reactions below, provide the missing products, indicate the likely intermediates and explain all routes yield a alcohol. ÇI 1. LİCH3, ether, rt 2. H;O* 1. CH,CH,MgBr, diethyl ether 2. НС, Н,О 1. (PHCH2),CuLi, THF Ph 2. HCС, Н,О

8. Organometallic reagents, such as organolithium (RLi), Gilman or Organo-cuprates (R2)CuLi) and Grignard (R MgBr), have been known to transform ketones and aldehyde molecules. Pages 1032-1033 show these reagents can modify acid chlorides, acid anhydrides and esters. OR Given the reactions below, provide the missing products, indicate the likely intermediates and explain all routes yield a alcohol. ÇI 1. LİCH3, ether, rt 2. H;O* 1. CH,CH,MgBr, diethyl ether 2. НС, Н,О 1. (PHCH2),CuLi, THF Ph 2. HCС, Н,О

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter21: Nas: Nucleophilic Aromatic Substitution

Section: Chapter Questions

Problem 7E

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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…
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…
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…
Organometallic reagents and alkoxides are strong bases as well as being good nucleophiles. Given the pKa values below, which reagent is the stronger base, nBuLi (CH3CH2CH2CH2LI) or the tert-butoxide anion ((CH3)3CO‒)? Explain your choice clearly in terms of structure andbonding. (Comparing the pKa values is not an explanation.) (CH3)3COH pka= 16.54CH3CH2CH2CH3 pka= 50
The two Grignard reactions and the reduction reaction below are all believed to have similar mechanisms. Use the curved arrow formalism to draw a single mechanism for these reactions using :Nuc-1 to indicate the nucleophile. The reacations are: cyclohexylmagnesium chloride + acetone in ether --> 2-cyclohexyl-2-propanol phenylmagnesium bromide + acetone in ether --> 2-phenyl-2-propanol Acetone + NaBH4 --> 2-propanol
In the reaction series below, write down the appropriate reagents that can be used where there are question marks.
For butenafine, develop a synthesis that starts with napthalene and benzene. (aromatic methyl groups can be converted to alkyl bromides using Br2/light, and aldehydes by heating the alkyl bromide in DMSO, eg. ArCH3 to ArCH2Br then to ArCHO).
4. using retrosynthetic analysis, determine which compounds could lead to the alkene shows below in a single step
10.1 Complete the following reactions: Show the step-by-step process. Do not use shortcut methods. Make it as detailed as it can be. Encode (not hand-written)!
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