Textbook Question
Each of these compounds can react as a nucleophile. In each case, use curved arrows to show how the nucleophile would react with the strong electrophile BF3.
(e) CH3CH2OH
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Ch. 2 - Acids and Bases; Functional Groups
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Chapter 2, Problem 53a,b
Each of these compounds can react as a nucleophile. In each case, use curved arrows to show how the nucleophile would react with the strong electrophile BF3.
(a) 
(b) 
Verified step by step guidance1
Identify the nucleophilic site in each compound. In compound (a), the oxygen atom in the carbonyl group is the nucleophilic site due to its lone pairs. In compound (b), the double bond can act as a nucleophile due to the pi electrons.
For compound (a), draw a curved arrow from one of the lone pairs on the oxygen atom to the boron atom in BF3. This represents the nucleophilic attack on the electrophile.
For compound (b), draw a curved arrow from the pi bond to the boron atom in BF3. This shows the nucleophilic attack by the pi electrons on the electrophile.
Explain that BF3 is a strong electrophile because boron has an incomplete octet and can accept electrons.
Discuss the result of these interactions: in both cases, the nucleophile donates electron density to the electrophile, forming a coordinate covalent bond.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Nucleophiles
Nucleophiles are species that donate an electron pair to form a chemical bond in a reaction. They are typically negatively charged or neutral molecules with lone pairs of electrons. Understanding the nature of nucleophiles is crucial for predicting how they will interact with electrophiles, such as BF3, which are electron-deficient and seek to accept electron pairs.
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Nucleophilic Addition
Electrophiles
Electrophiles are chemical species that accept an electron pair from nucleophiles during a reaction. They are often positively charged or neutral molecules with an incomplete octet, making them highly reactive. In this context, BF3 acts as a strong electrophile due to its ability to accept electron pairs, facilitating the nucleophilic attack.
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03:Nucleophile or Electrophile
Curved Arrows in Mechanisms
Curved arrows are used in organic chemistry to illustrate the movement of electron pairs during chemical reactions. The tail of the arrow indicates the source of the electrons, while the head points to where the electrons are going. This notation is essential for visualizing reaction mechanisms, particularly in nucleophilic attacks on electrophiles like BF3.
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Related Practice
Textbook Question
The pKa of ascorbic acid (vitamin C, page 55) is 4.17, showing that it is slightly more acidic than acetic acid (CH3COOH, pKa 4.74).
a. Show the four different conjugate bases that would be formed by deprotonation of the four different OH groups in ascorbic acid.
b. Compare the stabilities of these four conjugate bases, and predict which OH group of ascorbic acid is the most acidic.
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Textbook Question
Each of these compounds can react as an electrophile. In each case, use curved arrows to show how the electrophile would react with the strong nucleophile sodium ethoxide, Na+ −OCH2CH3.
a.
b. NH4+
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1
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Textbook Question
In each reaction, label the reactants as Lewis acids (electrophiles) or Lewis bases (nucleophiles). Use curved arrows to show the movement of electron pairs in the reactions. Draw any nonbonding electrons to show how they participate in the reactions.
c.
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Textbook Question
Each of these compounds can react as an electrophile. In each case, use curved arrows to show how the electrophile would react with the strong nucleophile sodium ethoxide, Na+ −OCH2CH3.
(c) CH3CH2Br
(d) BH3
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Textbook Question
Each of these compounds can react as a nucleophile. In each case, use curved arrows to show how the nucleophile would react with the strong electrophile BF3.
(f) (CH3)2S
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