problem 8.13 Draw the complete mechanism and the products for each of the following S2 reactions, paying close attention to stereochemistry. ONCHas Br ? ? CH3 (a) (b) Br Br (CHs),P: ? (c)

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...
icon
Related questions
icon
Concept explainers
Question

do 8.13!

**Problem 8.13**

Draw the complete mechanism and the products for each of the following S<sub>N</sub>2 reactions, paying close attention to stereochemistry.

**(a)** A bromine-substituted alkane reacting with iodide ion (I<sup>-</sup>).

- Reactants: A secondary alkyl bromide with a wedge symbol indicating stereochemistry, reacting with iodide ion.
- Expected to result in a product where the iodide ion replaces the bromine atom, with inversion of stereochemistry.

**(b)** A cyclic ammonium salt reacting with bromide ion (Br<sup>-</sup>).

- Reactants: A cyclic structure with a trimethylammonium group and methyl on one carbon, reacting with bromide ion.
- Expected to result in the bromide replacing the ammonium group, with specific stereochemical outcome.

**(c)** A benzyl bromide reacting with a phosphine nucleophile ((C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>P:).

- Reactants: A benzyl bromide with stereochemical indication, reacting with triphenylphosphine.
- Expected to yield a substitution product with consideration of the stereochemistry of the reaction.
Transcribed Image Text:**Problem 8.13** Draw the complete mechanism and the products for each of the following S<sub>N</sub>2 reactions, paying close attention to stereochemistry. **(a)** A bromine-substituted alkane reacting with iodide ion (I<sup>-</sup>). - Reactants: A secondary alkyl bromide with a wedge symbol indicating stereochemistry, reacting with iodide ion. - Expected to result in a product where the iodide ion replaces the bromine atom, with inversion of stereochemistry. **(b)** A cyclic ammonium salt reacting with bromide ion (Br<sup>-</sup>). - Reactants: A cyclic structure with a trimethylammonium group and methyl on one carbon, reacting with bromide ion. - Expected to result in the bromide replacing the ammonium group, with specific stereochemical outcome. **(c)** A benzyl bromide reacting with a phosphine nucleophile ((C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>P:). - Reactants: A benzyl bromide with stereochemical indication, reacting with triphenylphosphine. - Expected to yield a substitution product with consideration of the stereochemistry of the reaction.
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 3 images

Blurred answer
Knowledge Booster
Ideal and Real Gases
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