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Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination
Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
Chapter 12, Problem 14c

Suggest a reagent to carry out each of the following conversions to an alcohol.
(c)

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1
Analyze the given chemical structure. The starting material is a compound with a chlorine atom attached to a carbon chain containing a triple bond. The product is an alcohol with the hydroxyl group (-OH) replacing the chlorine atom.
Recognize that this transformation involves a substitution reaction where the chlorine atom is replaced by a hydroxyl group. This suggests the use of a nucleophilic substitution mechanism.
Identify the appropriate reagent for this substitution. A common reagent for replacing a halogen with a hydroxyl group is aqueous sodium hydroxide (NaOH) or potassium hydroxide (KOH). These reagents provide hydroxide ions (OH⁻) as nucleophiles.
Consider the reaction conditions. The reaction may require heating to facilitate the substitution process, as the bond between the carbon and chlorine is relatively strong.
Ensure that the triple bond in the molecule remains intact during the reaction. The chosen reagent and conditions should not affect the alkyne functional group.

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Key Concepts

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

Alcohol Functional Group

An alcohol is an organic compound characterized by the presence of one or more hydroxyl (-OH) groups attached to a carbon atom. Understanding the structure and reactivity of alcohols is crucial for predicting how they can be synthesized or converted from other functional groups.
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Reagents for Alcohol Synthesis

Various reagents can be used to convert different organic compounds into alcohols. Common reagents include reducing agents like lithium aluminum hydride (LiAlH4) or sodium borohydride (NaBH4), which can reduce carbonyl compounds (like aldehydes and ketones) to alcohols. Knowing the appropriate reagent for a specific conversion is essential for successful synthesis.
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Forming alcohols through Hydroboration-Oxidation.

Mechanism of Reduction Reactions

Reduction reactions involve the gain of electrons or hydrogen, often resulting in the conversion of a carbonyl group to an alcohol. Understanding the mechanism, including the role of nucleophiles and electrophiles, helps in predicting the outcome of the reaction and the conditions required for the conversion.
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