Identifying electron-donating and electron-withdrawing effectsFor each of the substituted benzene molecules below, determine the inductive and resonance effects the substituent will have on thebenzene ring, as well as the overall electron-density of the ring compared to unsubstituted benzene.MoleculeInductive EffectsResonance EffectsOverall Electron-DensityCF3O donatingO donatingO electron-richO withdrawingwithdrawingO no inductive effectsO no resonance effectsO electron-deficientO similar to benzeneOCH3ExplanationCheckO donatingO donating○ withdrawingwithdrawingO no inductive effectsno resonance effectselectron-richelectron-deficientO similar to benzeneХ© 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center

Answered: Identifying electron-donating and…

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter19: Eas: Electrophilic Aromatic Substitution

Section: Chapter Questions

Problem 19E

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Jj.198.
Give the stereochemical outcome for each of the followingreactions and assign the stereochemical relationship betweenthe products:
Reaction of C6H5CH2CH2OH with CH3COCl affords compound W, whichhas molecular formula C10H12O2. W shows prominent IR absorptions at3088–2897, 1740, and 1606 cm−1. W exhibits the following signals in its1H NMR spectrum: 2.02 (singlet), 2.91 (triplet), 4.25 (triplet), and 7.20–7.35(multiplet) ppm. What is the structure of W?
Cyclohex-2-enone has two protons on its carbon–carbon double bond (labeled Ha and Hb) and two protons on the carbon adjacent to the double bond (labeled Hc). (a) If Jab = 11 Hz and Jbc = 4 Hz, sketch the splitting pattern observed for each proton on the sp2 hybridized carbons. (b) Despite the fact that Ha is located adjacent to an electron-withdrawing C = O, its absorption occurs upfield from the signal due to Hb (6.0 vs. 7.0 ppm). Offer an explanation.
Identify the structures of D and E, isomers of molecular formulaC6H12O2, from their IR and 1H NMR data. Signals at 1.35 and 1.60 ppm inthe 1H NMR spectrum of D and 1.90 ppm in the 1H NMR spectrum of Eare multiplets
Please sol;;;!!!!:??
Draw the structure of a compound, C4H8O3 that exhibits IR absorptions at 1710 and 2500-3000 cm-1 and thefollowing 1H NMR signals: 11.1 (1H, singlet), 4.14 (2H, singlet), 3.63 (2H, quartet), 1.26 (3H, triplet) ppm.
Draw resonance forms for the sigma complexes resulting from electrophilic attackon substituted aromatic rings. Explain which substituents are activating and whichare deactivating, and show why they are ortho,para-directing, or meta-directing.
16 Draw the structures of Compound 16a and 16b, clearly indicate your assignments of all proton resonances. Calculate the unsaturation index of each compound Compound 16a- c8h6o2 A=10.2 ppm singlet 2h B=7.69 ppm singlet 4h Compound 16b C8H10 A=7.00 ppm, singlet 4h B= 2.25 ppm singlet 6H (Excess) H2NNH2, KOH, (HOCH2CH2)2O heat
On which ring and at what position/s would electrophilic aromatic substitution take place in the molecule below? Briefly account for your choice. A B CH3
For each of the substituted benzene molecules below, determine the inductive and resonance effects the substituent will have on the benzene ring, as well as the overall electron-density of the ring compared to unsubstituted benzene. Molecule CH3 Inductive Effects Odonating O withdrawing no inductive effects Odonating withdrawing Ono inductive effects Resonance Effects O donating O withdrawing Ono resonance effects. Odonating O withdrawing O no resonance effects Overall Electron-Density O electron-rich O electron-deficient Osimilar to benzene electron-rich: O electron-deficient Osimilar to benzene X
Which of the following is expected to result in the following compound ? EtCuLi CH;CH,MgBr OCH3 1) O3 2) DMSO two of the above are perfectly suitable

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