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Ch.11 - Reactions of Alcohols
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Non è quello che usi tu?Cambia libro di testo
Capitolo 11, Problema 1j,k,l

Classify each reaction as an oxidation, a reduction, or neither.
(j)
(k)
(l) Chemical reaction showing the conversion of a cyclohexene to cyclohexanol using BH3 and H2O2.

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1
Step 1: Analyze the first reaction (j). The starting material is cyclohexene, which undergoes reaction with a peroxyacid (RCO₃H) to form an epoxide. This is followed by hydrolysis with H₃O⁺ to produce a trans-diol. The formation of the epoxide involves the addition of oxygen, which is an oxidation process.
Step 2: Analyze the second reaction (k). Cyclohexene reacts with Cl₂ and H₂O to form a halohydrin. The addition of chlorine and hydroxyl groups does not involve a change in the oxidation state of the carbon atoms. Therefore, this reaction is classified as neither oxidation nor reduction.
Step 3: Analyze the third reaction (l). Cyclohexene undergoes hydroboration-oxidation using BH₃·THF followed by H₂O₂ and OH⁻ to form cyclohexanol. The addition of a hydroxyl group to the alkene involves the gain of hydrogen, which is a reduction process.
Step 4: Understand the definitions. Oxidation in organic chemistry typically involves the addition of oxygen or the removal of hydrogen, while reduction involves the addition of hydrogen or the removal of oxygen. Reactions that do not change the oxidation state are classified as neither.
Step 5: Summarize the classifications. Reaction (j) is an oxidation, reaction (k) is neither, and reaction (l) is a reduction.

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Oxidation and Reduction

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Oxidation states (or oxidation numbers) are a way to keep track of electron transfer in chemical reactions. Each element in a compound is assigned an oxidation state based on its electron configuration and bonding. By analyzing the changes in oxidation states of elements in a reaction, one can determine whether the reaction is an oxidation, reduction, or neither.
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