Organic Chemistry
3rd Edition
ISBN: 9781119338352
Author: Klein
Publisher: WILEY
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Question
Chapter 18.14, Problem 34CC
Interpretation Introduction
Interpretation:
The synthesis of anisole has to be illustrated using benzene as the starting compound.
Concept Introduction:
- Benzene is a stable aromatic compound and it is the simplest form of the
aromatic compounds . It is a very versatile compound that it furnishes various products with various reagents.
- The most common type of reactions that benzene undergoes is electrophilic substitution reactions.
- The various types of electrophilic substitution reactions in benzene are – Chlorination, Bromination, Nitration, Sulfonation, Friedel Crafts Alkylation/Acylation etc.
- So it is clear benzene can be converted to various range of compounds with appropriate reagents and reaction conditions. One of the useful method one can adapt to introduce any kind of group or atom onto the benzene ring is electrophilic substitution reaction.
- Aromatic compounds undergo another type of reactions called elimination – addition reaction. A compound with leaving group when treated with a strong base under high or low temperature undergoes elimination – addition reaction where the leaving group is eliminated and a new group is added. Halogens are known to be best leaving groups.
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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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* Hint: Think back to Chem 1 solubility rules.
Follow Up Questions for Part B
12. What impact do the following disturbances to a system at equilibrium have on k, the rate constant
for the forward reaction? Explain. (4 pts)
a) Changing the concentration of a reactant or product. (2 pts)
b) Changing the temperature of an exothermic reaction. (2 pts)
of
Chapter 18 Solutions
Organic Chemistry
Ch. 18.2 - Prob. 1CCCh. 18.3 - Prob. 2CCCh. 18.3 - Prob. 3CCCh. 18.4 - Prob. 4CCCh. 18.5 - Prob. 5CCCh. 18.5 - Prob. 6CCCh. 18.5 - Prob. 7CCCh. 18.6 - Prob. 8CCCh. 18.6 - Prob. 9CCCh. 18.6 - Prob. 10CC
Ch. 18.7 - Prob. 11CCCh. 18.7 - Prob. 12CCCh. 18.8 - Prob. 13CCCh. 18.9 - Prob. 14CCCh. 18.9 - Prob. 15CCCh. 18.10 - Prob. 1LTSCh. 18.10 - Prob. 16PTSCh. 18.11 - Prob. 2LTSCh. 18.11 - Prob. 18PTSCh. 18.11 - Prob. 19ATSCh. 18.11 - Prob. 3LTSCh. 18.11 - Prob. 20PTSCh. 18.11 - Prob. 21ATSCh. 18.11 - Prob. 4LTSCh. 18.11 - Prob. 22PTSCh. 18.11 - Prob. 23ATSCh. 18.12 - Prob. 24CCCh. 18.12 - Prob. 25CCCh. 18.12 - Prob. 5LTSCh. 18.12 - Prob. 26PTSCh. 18.12 - 2-Nitroaniline has been used as a precursor in the...Ch. 18.12 - Prob. 6LTSCh. 18.12 - Prob. 28PTSCh. 18.12 - Prob. 29ATSCh. 18.13 - Prob. 30CCCh. 18.13 - Prob. 31CCCh. 18.13 - Prob. 32CCCh. 18.14 - Prob. 33CCCh. 18.14 - Prob. 34CCCh. 18.15 - Prob. 7LTSCh. 18.15 - Prob. 35PTSCh. 18.15 - Prob. 36PTSCh. 18 - Prob. 38PPCh. 18 - Prob. 39PPCh. 18 - Prob. 40PPCh. 18 - Prob. 41PPCh. 18 - Prob. 42PPCh. 18 - Prob. 43PPCh. 18 - Prob. 44PPCh. 18 - Prob. 45PPCh. 18 - Prob. 46PPCh. 18 - Prob. 47PPCh. 18 - Prob. 48PPCh. 18 - Prob. 49PPCh. 18 - Prob. 50PPCh. 18 - Prob. 51PPCh. 18 - Prob. 52PPCh. 18 - Prob. 53PPCh. 18 - Prob. 54PPCh. 18 - Prob. 55PPCh. 18 - Prob. 56PPCh. 18 - Prob. 57PPCh. 18 - Prob. 58PPCh. 18 - Prob. 59PPCh. 18 - Prob. 60PPCh. 18 - Prob. 61PPCh. 18 - Prob. 62PPCh. 18 - Prob. 63PPCh. 18 - Prob. 64PPCh. 18 - When 2,4-dibromo-3-methyltolene is treated with...Ch. 18 - Prob. 66PPCh. 18 - Prob. 67PPCh. 18 - Prob. 68PPCh. 18 - Prob. 69PPCh. 18 - Prob. 70PPCh. 18 - Prob. 71PPCh. 18 - Prob. 72PPCh. 18 - Prob. 74IPCh. 18 - Prob. 75IPCh. 18 - Prob. 76IPCh. 18 - Prob. 77IPCh. 18 - Prob. 78IPCh. 18 - Prob. 79IPCh. 18 - Prob. 80IPCh. 18 - Prob. 81IPCh. 18 - Prob. 82IPCh. 18 - Prob. 83IPCh. 18 - Prob. 84IPCh. 18 - Prob. 85IPCh. 18 - Prob. 86IPCh. 18 - Prob. 87IPCh. 18 - Prob. 88IPCh. 18 - Prob. 89IPCh. 18 - Prob. 90IPCh. 18 - Prob. 91CPCh. 18 - Prob. 92CPCh. 18 - In the following reaction, iodine monochloride...Ch. 18 - Prob. 94CPCh. 18 - The following synthesis was developed in an...
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