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
552
views
Ch. 2 - Acids and Bases; Functional Groups
Wade9th EditionOrganic ChemistryISBN: 9780135213728
Not the one you use?Change textbookSelect a different textbook
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 52c,d
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
Verified step by step guidance1
Identify the electrophile in each compound. For CH3CH2Br, the electrophile is the carbon atom bonded to the bromine, as bromine is a good leaving group. For BH3, the boron atom is the electrophile due to its electron deficiency.
Consider the nucleophile, sodium ethoxide (Na+ −OCH2CH3). The ethoxide ion (−OCH2CH3) is the nucleophilic part, with the oxygen atom having a lone pair of electrons that can be donated.
For CH3CH2Br, draw a curved arrow from the lone pair on the oxygen of the ethoxide ion to the electrophilic carbon atom in CH3CH2Br. This represents the nucleophilic attack.
In the reaction with CH3CH2Br, also draw a curved arrow from the bond between the carbon and bromine to the bromine atom, indicating that the bromine will leave as a bromide ion (Br−).
For BH3, draw a curved arrow from the lone pair on the oxygen of the ethoxide ion to the boron atom. This represents the formation of a coordinate covalent bond between the nucleophile and the electrophile, as boron accepts the electron pair.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
5mWas this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Electrophile
An electrophile is a chemical species that accepts an electron pair from a nucleophile to form a chemical bond. Electrophiles are typically positively charged or neutral species with an electron-deficient atom. In the context of the question, CH3CH2Br and BH3 act as electrophiles, seeking electrons from the nucleophile sodium ethoxide.
Recommended video:
Guided course
03:
Nucleophile or Electrophile
Nucleophile
A nucleophile is a chemical species that donates an electron pair to an electrophile to form a chemical bond. Nucleophiles are typically negatively charged or neutral species with a lone pair of electrons. Sodium ethoxide (Na+ −OCH2CH3) acts as a strong nucleophile, with the ethoxide ion (−OCH2CH3) donating electrons to the electrophiles in the reaction.
Recommended video:
Guided course
08:27Nucleophilic Addition
Curved Arrow Notation
Curved arrow notation is used in organic chemistry to depict the movement of electron pairs during chemical reactions. The tail of the arrow starts at the electron pair donor (nucleophile) and points towards the electron pair acceptor (electrophile). In the given reactions, curved arrows will show the flow of electrons from the nucleophile sodium ethoxide to the electrophiles CH3CH2Br and BH3, illustrating the formation of new bonds.
Recommended video:
Guided course
06:20Alternative MO Notation for Dienes
Related Practice
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.
(b)
1531
views
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+
1650
views
1
rank
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.
750
views
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
609
views
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.
(a)
(b)
1209
views