Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 16, Problem 16.30SP
One of the following hydrocarbons is much more acidic than the others. Indicate which one and explain why it is unusually acidic.
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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
Inductive Effects
Resonance Effects
Overall Electron-Density
×
NO2
○ donating
O donating
O withdrawing
O withdrawing
O electron-rich
electron-deficient
no inductive effects
O no resonance effects
O similar to benzene
E
[
CI
O donating
withdrawing
O no inductive effects
Explanation
Check
○ donating
withdrawing
no resonance effects
electron-rich
electron-deficient
O similar to benzene
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Understanding how substituents activate
Rank each of the following substituted benzene molecules in order of which will react fastest (1) to slowest (4) by electrophilic
aromatic substitution.
Explanation
HN
NH2
Check
X
(Choose one)
(Choose one)
(Choose one)
(Choose one)
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Identifying electron-donating and electron-withdrawing effects on benzene
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.
Inductive Effects
Resonance Effects
Overall Electron-Density
Molecule
CF3
O donating
O donating
O withdrawing
O withdrawing
O no inductive effects
O no resonance effects
electron-rich
electron-deficient
O similar to benzene
CH3
O donating
O withdrawing
O no inductive effects
O donating
O withdrawing
Ono resonance effects
O electron-rich
O electron-deficient
O similar to benzene
Explanation
Check
Х
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Chapter 16 Solutions
Organic Chemistry (9th Edition)
Ch. 16.2 - Prob. 16.1PCh. 16.2 - Prob. 16.2PCh. 16.2 - a. Draw the resonance forms of benzene,...Ch. 16.2 - Show the product of the Diels-Alder dimerization...Ch. 16.4 - Prob. 16.5PCh. 16.6 - Make a model of cyclooctatetraene in the tub...Ch. 16.6 - Prob. 16.7PCh. 16.6 - Prob. 16.8PCh. 16.7 - Prob. 16.9PCh. 16.8A - a. Draw the molecular orbitals for the...
Ch. 16.8A - Repeat Problem16-10 for the cyclopentadienyl ions....Ch. 16.8C - Explain why each compound or ion should be...Ch. 16.8C - The following hydrocarbon has an unusually large...Ch. 16.8C - Prob. 16.14PCh. 16.8C - Prob. 16.15PCh. 16.9B - Prob. 16.16PCh. 16.9C - Show which of the nitrogen atoms in purine are...Ch. 16.9C - The proton NMR spectrum of 2-pyridone gives the...Ch. 16.9D - Prob. 16.19PCh. 16.9D - Prob. 16.20PCh. 16.10 - Prob. 16.21PCh. 16.12 - Ciprofloxacin is a member of the fluoroquinolone...Ch. 16.13 - Draw and name all the chlorinated benzenes having...Ch. 16.13 - Name the following compounds:Ch. 16.15 - The UV spectrum of 1-phenylprop-2-en-1-ol shows an...Ch. 16 - Prob. 16.26SPCh. 16 - Name the following compounds:Ch. 16 - Draw and name all the methyl, dimethyl, and...Ch. 16 - Four pairs of compounds are shown. In each pair,...Ch. 16 - One of the following hydrocarbons is much more...Ch. 16 - In Kekuls time cyclohexane was unknown, and there...Ch. 16 - Prob. 16.32SPCh. 16 - Azulene is a deep-blue hydrocarbon with resonance...Ch. 16 - Prob. 16.34SPCh. 16 - Prob. 16.35SPCh. 16 - Prob. 16.36SPCh. 16 - Prob. 16.37SPCh. 16 - Prob. 16.38SPCh. 16 - Prob. 16.39SPCh. 16 - Biphenyl has the following structure. a. Is...Ch. 16 - Anions of hydrocarbons are rare, and dianions of...Ch. 16 - How would you convert the following compounds to...Ch. 16 - Prob. 16.43SPCh. 16 - Prob. 16.44SPCh. 16 - A student found an old bottle labeled thymol on...Ch. 16 - Prob. 16.46SPCh. 16 - Prob. 16.47SPCh. 16 - Prob. 16.48SPCh. 16 - The proton NMR chemical shifts of the hydrogens in...Ch. 16 - Prob. 16.50SPCh. 16 - NMR has been used to probe many molecular...
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- + C8H16O2 (Fatty acid) + 11 02 → 8 CO2 a. Which of the above are the reactants? b. Which of the above are the products? H2o CO₂ c. Which reactant is the electron donor? Futty acid d. Which reactant is the electron acceptor? e. Which of the product is now reduced? f. Which of the products is now oxidized? 02 #20 102 8 H₂O g. Where was the carbon initially in this chemical reaction and where is it now that it is finished? 2 h. Where were the electrons initially in this chemical reaction and where is it now that it is finished?arrow_forward→ Acetyl-CoA + 3NAD+ + 1FAD + 1ADP 2CO2 + CoA + 3NADH + 1FADH2 + 1ATP a. Which of the above are the reactants? b. Which of the above are the products? c. Which reactant is the electron donor? d. Which reactants are the electron acceptors? e. Which of the products are now reduced? f. Which product is now oxidized? g. Which process was used to produce the ATP? h. Where was the energy initially in this chemical reaction and where is it now that it is finished? i. Where was the carbon initially in this chemical reaction and where is it now that it is finished? j. Where were the electrons initially in this chemical reaction and where is it now that it is finished?arrow_forwardRank each of the following substituted benzene molecules in order of which will react fastest (1) to slowest (4) by electrophilic aromatic substitution. OCH 3 (Choose one) OH (Choose one) Br (Choose one) Explanation Check NO2 (Choose one) © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center | Aarrow_forward
- 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 Inductive Effects O donating O withdrawing O no inductive effects Resonance Effects Overall Electron-Density ○ donating ○ withdrawing O no resonance effects O electron-rich O electron-deficient O similar to benzene Cl O donating O withdrawing ○ donating ○ withdrawing O no inductive effects O no resonance effects O Explanation Check O electron-rich O electron-deficient similar to benzene X © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center | Accessarrow_forwardIdentifying electron-donating and 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 Inductive Effects NH2 ○ donating NO2 Explanation Check withdrawing no inductive effects Resonance Effects Overall Electron-Density ○ donating O withdrawing O no resonance effects O donating O withdrawing O donating withdrawing O no inductive effects Ono resonance effects O electron-rich electron-deficient O similar to benzene O electron-rich O electron-deficient O similar to benzene olo 18 Ar 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center | Accessibilityarrow_forwardRank each of the following substituted benzene molecules in order of which will react fastest (1) to slowest (4) by electrophilic aromatic substitution. Explanation Check Х (Choose one) OH (Choose one) OCH3 (Choose one) OH (Choose one) © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Centerarrow_forward
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