Identifying electron-donating and electron-withdrawing effects on benzeneFor 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.Inductive EffectsResonance EffectsOverall Electron-DensityMoleculeCF3O donatingO donatingO withdrawingO withdrawingO no inductive effectsO no resonance effectselectron-richelectron-deficientO similar to benzeneCH3O donatingO withdrawingO no inductive effectsO donatingO withdrawingOno resonance effectsO electron-richO electron-deficientO similar to benzeneExplanationCheckХ© 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center

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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:
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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.
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
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
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
Reaction of p-cresol with two equivalents of 2-methylprop-1-ene affordsBHT, a preservative with molecular formula C15H24O. BHT gives thefollowing 1H NMR spectral data: 1.4 (singlet, 18 H), 2.27 (singlet, 3 H), 5.0(singlet, 1 H), and 7.0 (singlet, 2 H) ppm. What is the structure of BHT?Draw a stepwise mechanism illustrating how it is formed.
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?
A C5H8 alkyne is reacted with Lindlar's catalyst and hydrogen gas to yield product with the following H NMR resonances. Provide the structure for Product A and the alkyne 0.78 ppm triplet 3H 1.60 ppm doublet 3H 2.05 ppm doublet of quartets 2H 5.40 ppm doublet of quartets 1H 5.34 ppm doublet of triplets 1H
Identify A, B, and C, intermediates in the synthesis of the five-membered ring called an α- methylene-γ-butyrolactone. This heterocyclic ring system is present in some antitumor agents.
Reaction of p-cresol with two equivalents of 2-methylprop-1-ene affords BHT, a preservative with molecular formula C15H24O. BHT gives the following 1H NMR spectral data: 1.4 (singlet, 18 H), 2.27 (singlet, 3 H), 5.0 (singlet, 1 H), and 7.0 (singlet, 2 H) ppm. What is the structure of BHT? Draw a stepwise mechanism illustrating how it is formed.

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