Rimantadine was among the first antiviral drugs to be licensed in the United States to use against the influenza A virus and to treat established illnesses. It is synthesized from adamantane by the following sequence:
Rimantadine was among the first antiviral drugs to be licensed in the United States to use against the influenza A virus and to treat established illnesses. It is synthesized from adamantane by the following sequence:
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...
Related questions
Question
What is the structure of nucleophile 3? Thank you.
Transcribed Image Text:Rimantadine was among the first antiviral drugs to be licensed in the United States to use against the influenza A virus and to treat established illnesses. It is
synthesized from adamantane by the following sequence:
CH₂=CHBr
AlBr3
(2)
Adamantane
=D₂.-6.
(3)
-Br
Br
(4)
Ø
Br₂
(1)
a Step 2 proceeds via the following mechanism:
1-bromoadamantane
(5)
Br
SnF
ChemDoodle
Rimantadine
1. AlBr, acts as a Lewis acid to yield carbocation 1;
2. Bromoethene acts as a nucleophile to give carbocation 2;
3. Carbocation 2 reacts with nucleophile 3 to give the product of reaction 2.
Work out this mechanism on a separate sheet of paper and then draw the structure of nucleophile 3.
NH₂
==starting points == ✔
Expert Solution
This question has been solved!
Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.
Step by step
Solved in 2 steps with 2 images
Knowledge Booster
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.Recommended textbooks for you
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY