
ORGANIC CHEMISTRY
9th Edition
ISBN: 9780134645704
Author: WADE AND SIMEK
Publisher: PEARSON
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Question
Chapter 7.11, Problem 7.21P
Interpretation Introduction
Interpretation:
The structures of the two substitution products formed in the given reaction are to be given.
Concept introduction:
Substitution reactions are the reactions in which there is replacement of an atom or a
Elimination reactions are the reaction in which
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Identifying 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
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Rank 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)
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Assign R or S to all the chiral centers in each compound drawn below
porat
bg
9
Br
Br
Chapter 7 Solutions
ORGANIC CHEMISTRY
Ch. 7.3A - Prob. 7.1PCh. 7.3A - Prob. 7.2PCh. 7.3B - Draw five more compounds of formula C4H6NOC1.Ch. 7.3B - For each of the following molecular formulas,...Ch. 7.4 - Give the systematic (IUPAC) names of the following...Ch. 7.5B - The following names are all incorrect. Draw the...Ch. 7.5B - Prob. 7.8PCh. 7.5B - a. How many stereogcmc double bonds are in...Ch. 7.6 - Teflon-coated frying pans routinely endure...Ch. 7.7B - Prob. 7.11P
Ch. 7.8B - Use the data in Table7-2 to predict the energy...Ch. 7.8C - Prob. 7.13PCh. 7.8E - Explain why each of the following alkenes is...Ch. 7.8F - Prob. 7.15PCh. 7.10 - Prob. 7.16PCh. 7.10A - SN1 substitution and E1 elimination frequently...Ch. 7.10C - Prob. 7.18PCh. 7.10C - Prob. 7.19PCh. 7.10C - Prob. 7.20PCh. 7.11 - Prob. 7.21PCh. 7.11 - Prob. 7.22PCh. 7.12 - Prob. 7.23PCh. 7.12 - Prob. 7.24PCh. 7.13 - Prob. 7.25PCh. 7.14B - Prob. 7.26PCh. 7.14B - Make models of the blowing compounds, and predict...Ch. 7.15 - Prob. 7.28PCh. 7.15 - Prob. 7.29PCh. 7.15 - Prob. 7.30PCh. 7.15 - Prob. 7.31PCh. 7.16 - Predict the major and minor elimination products...Ch. 7.17B - Predict the products and mechanisms of the...Ch. 7.18 - Propose mechanisms for the following reactions.Ch. 7.18 - Prob. 7.35PCh. 7.19B - The dehydrogenation of butane to trans-but-2-ene...Ch. 7.19B - Prob. 7.37PCh. 7.19B - Prob. 7.38PCh. 7.19B - Prob. 7.39PCh. 7 - Prob. 7.40SPCh. 7 - Prob. 7.41SPCh. 7 - Prob. 7.42SPCh. 7 - Prob. 7.43SPCh. 7 - Prob. 7.44SPCh. 7 - Prob. 7.45SPCh. 7 - Prob. 7.46SPCh. 7 - The energy difference between cis- and...Ch. 7 - Prob. 7.48SPCh. 7 - Prob. 7.49SPCh. 7 - Prob. 7.50SPCh. 7 - What halides would undergo E2 dehydrohalogenation...Ch. 7 - Prob. 7.52SPCh. 7 - Prob. 7.53SPCh. 7 - Write a balanced equation for each reaction,...Ch. 7 - Prob. 7.55SPCh. 7 - Using cyclohexane as your starting material, show...Ch. 7 - Show how you would prepare cyclopentene from each...Ch. 7 - Prob. 7.58SPCh. 7 - E1 eliminations of alkyl halides are rarely useful...Ch. 7 - Prob. 7.60SPCh. 7 - Propose mechanisms for the following reactions....Ch. 7 - Prob. 7.62SPCh. 7 - Prob. 7.63SPCh. 7 - Prob. 7.64SPCh. 7 - Prob. 7.65SPCh. 7 - Prob. 7.66SPCh. 7 - Prob. 7.67SPCh. 7 - Prob. 7.68SPCh. 7 - Prob. 7.69SPCh. 7 - Explain the dramatic difference in rotational...Ch. 7 - One of the following dichloronorbornanes undergoes...Ch. 7 - A graduate student wanted to make...Ch. 7 - Prob. 7.73SPCh. 7 - Prob. 7.74SPCh. 7 - Prob. 7.75SPCh. 7 - Prob. 7.76SP
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- (c) (4pts) Mechanism: heat (E1) CH3OH + 1.5pts each _E1 _ (1pt) Br CH3OH (d) (4pts) Mechanism: SN1 (1pt) (e) (3pts) 1111 I H 10 Ill!! H LDA THF (solvent) Mechanism: E2 (1pt) NC (f) Bri!!!!! CH3 NaCN (3pts) acetone Mechanism: SN2 (1pt) (SN1) -OCH3 OCH3 1.5pts each 2pts for either product 1pt if incorrect stereochemistry H Br (g) “,、 (3pts) H CH3OH +21 Mechanism: SN2 (1pt) H CH3 2pts 1pt if incorrect stereochemistry H 2pts 1pt if incorrect stereochemistryarrow_forwardA mixture of butyl acrylate and 4'-chloropropiophenone has been taken for proton NMR analysis. Based on this proton NMR, determine the relative percentage of each compound in the mixturearrow_forwardQ5: Label each chiral carbon in the following molecules as R or S. Make sure the stereocenter to which each of your R/S assignments belong is perfectly clear to the grader. (8pts) R OCH 3 CI H S 2pts for each R/S HO R H !!! I OH CI HN CI R Harrow_forward
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