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Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives
Bruice - Organic Chemistry 8th Edition
Bruice8th EditionOrganic ChemistryISBN: 9780135213711Not the one you use?Change textbook
Chapter 16, Problem 50f

What compounds are formed from the reaction of benzoyl chloride with the following reagents?
f. cyclohexanol

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1
Identify the functional group in benzoyl chloride. Benzoyl chloride contains an acyl chloride group (-COCl), which is highly reactive and undergoes nucleophilic acyl substitution reactions.
Recognize the functional group in cyclohexanol. Cyclohexanol is an alcohol, containing a hydroxyl group (-OH), which can act as a nucleophile in the reaction.
Understand the reaction mechanism. The hydroxyl group of cyclohexanol will attack the carbonyl carbon of benzoyl chloride, displacing the chloride ion (Cl⁻) as a leaving group. This is a nucleophilic acyl substitution reaction.
Predict the product. The reaction will result in the formation of an ester, specifically cyclohexyl benzoate, where the cyclohexyl group is attached to the benzoate moiety.
Write the general reaction equation: C6H5(COCl)+C6H11OHC6H5(COOC6H11)+HCl. This shows the formation of cyclohexyl benzoate and HCl as a byproduct.

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Key Concepts

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

Benzoyl Chloride

Benzoyl chloride is an acyl chloride derived from benzoic acid. It is a reactive compound that can undergo nucleophilic acyl substitution reactions. In the presence of alcohols, such as cyclohexanol, benzoyl chloride can react to form esters through the nucleophilic attack of the alcohol on the carbonyl carbon, releasing hydrochloric acid as a byproduct.
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Nucleophilic Acyl Substitution

Nucleophilic acyl substitution is a fundamental reaction in organic chemistry where a nucleophile attacks the electrophilic carbon of a carbonyl group, leading to the substitution of a leaving group. In the case of benzoyl chloride reacting with cyclohexanol, the hydroxyl group of cyclohexanol acts as the nucleophile, resulting in the formation of an ester, specifically cyclohexyl benzoate.
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Formation of Esters

Esters are organic compounds formed from the reaction of an alcohol and a carboxylic acid or its derivatives, such as acyl chlorides. The reaction typically involves the nucleophilic attack of the alcohol on the carbonyl carbon of the acyl compound, followed by the elimination of a small molecule, often water or hydrochloric acid. In this case, cyclohexanol reacts with benzoyl chloride to yield cyclohexyl benzoate.
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