For each reaction in question 20, sketch a reaction coordinate energy diagram indicating the starting materials, transition states and any intermediates, if present, in the reaction

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

For each reaction in question 20, sketch a reaction coordinate energy diagram indicating the starting materials, transition states and any intermediates, if present, in the reaction. Don't worry about the absolute energy of starting materials and products but you can assume that the product is more stable than the starting materials. 

20. When the acetate of (S)-2-pentanol is heated in water which contains ammonium
chloride, a racemic mixture of (S)- and (R)-2-chloropentane is produced (reaction
A). When the same reaction is carried out in dimethylformamide (DMF) as the
solvent, only the (R) product is obtained (reaction B). Answer the following about
these reactions:
NH,CI, H,O
A
heat
50:50
NHẠCI, DMF
B
only product
heat
a. By what mechanism are these reactions proceeding? (circle the correct
mechanism)
Reaction A:
SN1
Sx2
El
E2
Reaction B:
Syl
Sx2
E1
E2
b. Why did reaction A give a mixture of products? Be sure to use and orbital
argument to support your answer.
Transcribed Image Text:20. When the acetate of (S)-2-pentanol is heated in water which contains ammonium chloride, a racemic mixture of (S)- and (R)-2-chloropentane is produced (reaction A). When the same reaction is carried out in dimethylformamide (DMF) as the solvent, only the (R) product is obtained (reaction B). Answer the following about these reactions: NH,CI, H,O A heat 50:50 NHẠCI, DMF B only product heat a. By what mechanism are these reactions proceeding? (circle the correct mechanism) Reaction A: SN1 Sx2 El E2 Reaction B: Syl Sx2 E1 E2 b. Why did reaction A give a mixture of products? Be sure to use and orbital argument to support your answer.
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 1 images

Blurred answer
Knowledge Booster
Catalysis and Enzymatic 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
  • SEE MORE 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