Textbook Question
The following compounds can all react as acids.
a. For each compound, show its conjugate base. Show any resonance forms if applicable. b. Rank the conjugate bases in the order you would predict, from most stable to least stable.
3. Acids and Bases
Acids and Bases
5:25 minutesProblem 52e,f
Textbook Question
What products are formed when each of the following reacts with HO−?
e. +CH3
f. FeBr3
Verified step by step guidance1
Step 1: For part (e), consider the reaction of the methyl cation (+CH3) with hydroxide ion (HO−). The methyl cation is a highly reactive electrophile, and the hydroxide ion is a strong nucleophile. Analyze the nucleophilic attack of HO− on the positively charged carbon of +CH3.
Step 2: Write the reaction mechanism for part (e). The hydroxide ion donates a lone pair of electrons to the carbon atom of +CH3, forming a new C-O bond. This results in the formation of methanol (CH3OH).
Step 3: For part (f), consider the reaction of FeBr3 with hydroxide ion (HO−). FeBr3 is a Lewis acid, and hydroxide ion is a strong base. Analyze the acid-base interaction between FeBr3 and HO−.
Step 4: Write the reaction mechanism for part (f). The hydroxide ion reacts with FeBr3, leading to the formation of a ferric hydroxide complex (Fe(OH)3) and bromide ions (Br−).
Step 5: Summarize the products for both reactions. For part (e), the product is methanol (CH3OH). For part (f), the products are Fe(OH)3 and Br−. Ensure the reaction mechanisms are balanced and consistent with the principles of organic and inorganic chemistry.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Nucleophilic Attack
Nucleophilic attack is a fundamental reaction mechanism in organic chemistry where a nucleophile, such as hydroxide ion (HO−), donates a pair of electrons to an electrophile, forming a new bond. Understanding this concept is crucial for predicting the products of reactions, as it determines how reactants interact and what new compounds are formed.
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Electrophiles
Electrophiles are species that accept electron pairs from nucleophiles during chemical reactions. They are typically positively charged or have a partial positive charge, making them attractive to nucleophiles. Identifying the electrophiles in a reaction is essential for determining the products formed when they react with nucleophiles like HO−.
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Reaction Conditions
Reaction conditions, including the presence of solvents, temperature, and catalysts, significantly influence the outcome of chemical reactions. In the context of the question, understanding how HO− interacts with different reactants under specific conditions helps predict the nature of the products formed, such as whether substitution or elimination reactions occur.
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