Homework Help is Here – Start Your Trial Now!
Science
Chemistry
16) Which of the following compounds is the most nucleophilic? A) CH3SH B) CH3OH C) H20 D) CH3CO2H E) BF3

16) Which of the following compounds is the most nucleophilic? A) CH3SH B) CH3OH C) H20 D) CH3CO2H E) BF3

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
See similar textbooks
icon
Related questions
Question
**Question 16: Determining the Most Nucleophilic Compound** In this question, students are asked to identify which compound is the most nucleophilic among the following options: A) CH₃SH B) CH₃OH C) H₂O D) CH₃CO₂H E) BF₃ **Explanation:** Nucleophilicity refers to the ability of a compound to donate an electron pair. This property is influenced by factors such as the presence of lone pairs, the electronegativity of atoms, and the steric hindrance around the reactive site. **Option Analysis:** - **A) CH₃SH (Methanethiol)**: Contains a sulfur atom with lone pairs, making it a strong nucleophile due to the reduced electronegativity of sulfur compared to oxygen. - **B) CH₃OH (Methanol)**: Contains an oxygen atom with lone pairs; however, oxygen is more electronegative than sulfur, making it less nucleophilic than CH₃SH. - **C) H₂O (Water)**: Similar to methanol, but without the alkyl group which somewhat stabilizes the negative charge. - **D) CH₃CO₂H (Acetic Acid)**: While it has an oxygen atom with lone pairs, the presence of the carbonyl group decreases its nucleophilicity through resonance. - **E) BF₃ (Boron Trifluoride)**: Acts as an electrophile rather than a nucleophile due to its electron-deficient boron atom. **Conclusion:** - **Answer: A) CH₃SH** is the most nucleophilic compound, as sulfur's larger atomic size and lower electronegativity compared to oxygen increase its nucleophilic characteristics.
Transcribed Image Text:**Question 16: Determining the Most Nucleophilic Compound** In this question, students are asked to identify which compound is the most nucleophilic among the following options: A) CH₃SH B) CH₃OH C) H₂O D) CH₃CO₂H E) BF₃ **Explanation:** Nucleophilicity refers to the ability of a compound to donate an electron pair. This property is influenced by factors such as the presence of lone pairs, the electronegativity of atoms, and the steric hindrance around the reactive site. **Option Analysis:** - **A) CH₃SH (Methanethiol)**: Contains a sulfur atom with lone pairs, making it a strong nucleophile due to the reduced electronegativity of sulfur compared to oxygen. - **B) CH₃OH (Methanol)**: Contains an oxygen atom with lone pairs; however, oxygen is more electronegative than sulfur, making it less nucleophilic than CH₃SH. - **C) H₂O (Water)**: Similar to methanol, but without the alkyl group which somewhat stabilizes the negative charge. - **D) CH₃CO₂H (Acetic Acid)**: While it has an oxygen atom with lone pairs, the presence of the carbonyl group decreases its nucleophilicity through resonance. - **E) BF₃ (Boron Trifluoride)**: Acts as an electrophile rather than a nucleophile due to its electron-deficient boron atom. **Conclusion:** - **Answer: A) CH₃SH** is the most nucleophilic compound, as sulfur's larger atomic size and lower electronegativity compared to oxygen increase its nucleophilic characteristics.
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps

SEE SOLUTIONCheck out a sample Q&A here
Blurred answer
Knowledge Booster
Selection Rules for Pericyclic Reactions
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY
SEE MORE TEXTBOOKS