Textbook Question
Show an arrow-pushing mechanism that forms the product on the right from the reactant at left. Only one arrow is necessary in each reaction. [Don't forget to draw in the lone pairs on this and the next two assessments.]
(a)
3. Acids and Bases
Reaction Mechanism
3:45 minutesProblem 55b
Textbook Question
Identify the nucleophile and the electrophile in each of the following reactions.
(b) 
Verified step by step guidance1
Step 1: Understand the definitions of nucleophile and electrophile. A nucleophile is a species that donates a pair of electrons to form a new covalent bond, often rich in electron density (e.g., lone pairs, π bonds, or negative charges). An electrophile is a species that accepts a pair of electrons to form a new covalent bond, often electron-deficient (e.g., positive charges, partial positive charges, or empty orbitals).
Step 2: Analyze the reaction provided. Look at the reactants and identify which species has electron-rich regions (potential nucleophile) and which species has electron-deficient regions (potential electrophile).
Step 3: Examine functional groups or charges. For example, if one reactant has a lone pair of electrons or a negative charge, it is likely the nucleophile. If another reactant has a positive charge, partial positive charge, or an electron-deficient atom, it is likely the electrophile.
Step 4: Consider the mechanism of the reaction. Determine which species initiates the reaction by donating electrons (nucleophile) and which species accepts those electrons (electrophile).
Step 5: Assign the roles. Clearly label the nucleophile and electrophile based on the analysis. For example, if a hydroxide ion (OH⁻) reacts with a carbonyl compound, the hydroxide ion is the nucleophile, and the carbonyl carbon (C=O) is the electrophile due to its partial positive charge on the carbon.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Nucleophile
A nucleophile is a species that donates an electron pair to form a chemical bond in a reaction. Nucleophiles are typically negatively charged or neutral molecules with lone pairs of electrons, allowing them to attack positively charged or electron-deficient centers. Understanding the nature of nucleophiles is crucial for predicting reaction mechanisms and outcomes in organic chemistry.
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Electrophile
An electrophile is a chemical species that accepts an electron pair from a nucleophile during a reaction. Electrophiles are often positively charged or have a partial positive charge due to electronegative atoms nearby. Recognizing electrophiles is essential for understanding how reactions proceed, as they are the targets for nucleophilic attack.
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Reaction Mechanism
A reaction mechanism describes the step-by-step process by which reactants transform into products, detailing the movement of electrons and the formation and breaking of bonds. Understanding reaction mechanisms is vital for predicting the behavior of nucleophiles and electrophiles in various reactions, as it provides insight into the intermediates and transition states involved.
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