Textbook Question
Identify the nucleophile and the electrophile in each of the following reactions.
(b)
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Ch. 4 - Acids and Bases: Electron Flow
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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Table of contents
- Ch. 2 - General Chemistry Translated: Finding the Electrons114
- Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis109
- Ch. 4 - Acids and Bases: Electron Flow144
- Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics118
- Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space112
- Ch. 7 - Principles of Green (Organic) Chemistry3
- Ch. 8 - Alkenes I: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes II: Oxidation and Reduction150
- Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions101
- Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions108
- Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes172
- Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination239
- Ch. 14 - Structural Identification I: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems I: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems II: Pericyclic Reactions54
- Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene II: Reactions Influenced by the Aromatic Ring62
- Ch. 25 - Amines: Structure, Reactions, and Synthesis27
- Ch. 26 - Amino Acids, Proteins, and Peptide Synthesis9
- Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids54
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
Chapter 3, Problem 55a
Identify the nucleophile and the electrophile in each of the following reactions.
(a) 
Verified step by step guidance1
Step 1: Analyze the reaction provided in the image. The reaction involves methanol (CH₃OH) and a tertiary alcohol with a positively charged oxygen atom (OH⁺). The arrow indicates the movement of electrons from the lone pair on the oxygen atom of methanol to the positively charged oxygen atom of the tertiary alcohol.
Step 2: Define the nucleophile. A nucleophile is a species that donates a pair of electrons to form a bond. In this reaction, methanol (CH₃OH) acts as the nucleophile because its oxygen atom has lone pairs of electrons that can be donated.
Step 3: Define the electrophile. An electrophile is a species that accepts a pair of electrons to form a bond. In this reaction, the positively charged oxygen atom (OH⁺) of the tertiary alcohol acts as the electrophile because it is electron-deficient and can accept electrons.
Step 4: Explain the interaction. The lone pair of electrons on the oxygen atom of methanol is attracted to the positively charged oxygen atom of the tertiary alcohol. This results in the formation of a new bond between the oxygen atoms.
Step 5: Summarize the roles. Methanol (CH₃OH) is the nucleophile, donating electrons, and the positively charged oxygen atom (OH⁺) of the tertiary alcohol is the electrophile, accepting electrons.
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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. In the provided reaction, the hydroxide ion (OH-) acts as a nucleophile, attacking the electrophile to form a new bond.
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08:27
Nucleophilic Addition
Electrophile
An electrophile is a chemical species that accepts an electron pair from a nucleophile during a reaction. Electrophiles are usually positively charged or electron-deficient species. In the given reaction, the carbon atom in the alcohol group (attached to the hydroxyl group) acts as the electrophile, as it is susceptible to attack by the nucleophile.
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03:Nucleophile or Electrophile
Reaction Mechanism
A reaction mechanism describes the step-by-step sequence of elementary reactions by which overall chemical change occurs. Understanding the mechanism helps in identifying the roles of nucleophiles and electrophiles in a reaction. In this case, the mechanism illustrates how the nucleophile attacks the electrophile, leading to the formation of a new product.
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Related Practice
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)
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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.]
(d)
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Textbook Question
The nitrogen screened in purple in Figure 4.43 is not protonated at physiological pH. Why?
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Textbook Question
Identify the most acidic proton in each pair. Tell which structural features you analyzed and why you weighted them as you did in picking one answer. [Always start by drawing the conjugate base.]
(h)
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Textbook Question
Identify the Lewis acid and the Lewis base in each of the following reactions.
(c)