Ch. 24 - Benzene II: Reactions Influenced by the Aromatic Ring

Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition

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Mullins 1st Edition

Ch. 24 - Benzene II: Reactions Influenced by the Aromatic Ring

Problem 4

Chapter 23, Problem 4

Calculate the oxidation number of the indicated atoms in the following reaction.

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Identify the atoms in the reaction for which you need to calculate the oxidation numbers. Typically, these are the atoms that undergo a change in oxidation state during the reaction.

Recall the general rules for assigning oxidation numbers: (1) The oxidation number of an atom in its elemental form is 0. (2) For monoatomic ions, the oxidation number is equal to the charge of the ion. (3) Oxygen usually has an oxidation number of -2, and hydrogen usually has +1. (4) The sum of oxidation numbers in a neutral compound is 0, and in a polyatomic ion, it is equal to the ion's charge.

Apply these rules to assign oxidation numbers to each atom in the reactants and products. Start with atoms that have known oxidation states, such as oxygen and hydrogen, to help deduce the oxidation states of other atoms.

Compare the oxidation numbers of the indicated atoms in the reactants and products. Determine if there is an increase or decrease in the oxidation number, which indicates oxidation or reduction, respectively.

Summarize the changes in oxidation numbers to identify which atoms are oxidized and which are reduced. This will help in understanding the redox process occurring in the reaction.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Oxidation Number

The oxidation number, or oxidation state, is a theoretical charge assigned to an atom in a molecule or ion, reflecting its degree of oxidation. It helps in tracking electron transfer in redox reactions. The rules for determining oxidation numbers include assigning -2 to oxygen, +1 to hydrogen, and using the charge of ions to deduce the oxidation states of other elements.

Redox Reactions

Redox reactions involve the transfer of electrons between two species, leading to changes in their oxidation states. Oxidation refers to the loss of electrons, while reduction refers to the gain of electrons. Understanding redox reactions is crucial for calculating oxidation numbers, as it helps identify which atoms are oxidized and which are reduced.

Balancing Chemical Equations

Balancing chemical equations ensures that the number of atoms for each element is equal on both sides of the reaction, maintaining the law of conservation of mass. In redox reactions, balancing also involves ensuring that the total increase in oxidation numbers equals the total decrease, which is essential for accurately determining the oxidation states of atoms.

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Related Practice

Textbook Question

Look closely at the resonance structures of the benzylic anions, radicals, and cations in Figures 24.2–24.4. On which benzene carbons did the charge/radical exist in the resonance structures—that is, were they ortho, meta, or para?

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Textbook Question

A carboxylic acid ( pK_a = 5) is 10¹¹ times more acidic than an alcohol (pK_a = 16). Why?

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Textbook Question

What is the product of the following reaction?

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Textbook Question

Which haloalkane would you expect to undergo the fastest S_N1 reaction? Why?

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Textbook Question

Provide an arrow-pushing mechanism for the following alkane bromination. [Don't forget to use fishhook arrows to represent the movement of single electrons.]

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Textbook Question

What reagent would you use to brominate the allylic carbon of cyclohexene?

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