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aniked [119]
4 years ago
13

Which of the following two combinations of reactants is more appropriate for the preparation of p-nitrophenyl phenyl ether? Fluo

robenzene and sodium p-nitrophenoxide, or p-fluoronitrobenzene and sodium phenoxide.

Chemistry
1 answer:
VladimirAG [237]4 years ago
5 0

Answer:

p-fluoronitrobenzene and sodium phenoxide is more appropriate

Explanation:

An ipso substitution is required to form p-nitrophenyl phenyl ether.

For this ipso substitution, an alkoxide anion needs to attack as a nucleophile at the carbon atom attached to fluorine atom and thereby substitute that F atom.

p-nitrophenoxide is an weak nucleophile as compared to phenoxide due to presence of electron withdrawing resonating effect of nitro group at para position.

p-fluoronitrobenzene is a good choice for nucleophilic attack by alkoxide anion as compared to fluorobenzene due to higher positive charge density at carbon atom directly attached to F atom. Higher positive charge density arises due to presence of electron withdrawing resonating effect og nitro group at para position.

So, p-fluoronitrobenzene and sodium phenoxide is more appropriate

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See attached => LeChatelier's Principle

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The attached notes explain in general terms how to evaluate a chemical reaction under an applied stress factor and determine direction of shift to establish a new equilibrium stability. Compare and apply to the worksheet problems.

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Answers to worksheet (compare to attached notes)

1a. => increasing wt to product side => tilts right => shifts left

1b. => removing wt from reactant side => tilts right => shifts left,

1c. => increasing wt to product side => tilts right => shifts left

2a. => tilts left (excess wt from Hg), shifts right,

2b. => Increase pressure shifts toward lower molar gas volume side (right) Note: apply only to gas phase substances, Hg is in liquid phase.

3a. exothermic rxn => cooling => tilts left, rxn shifts right

3b. endothermic rxn => cooling => tilts right, rxn shifts left

3c. exothermic rxn => cooling => tilts left, rxn shifts right

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Answer:

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