-bromo-1-methylcyclopentane is being reacted with sodium ethoxide in diethyl ether Ethoxide will remove a proton from one of the carbons alpha to the carbon bonded to bromine. The electron pair from the carbon-hydrogen bond will move toward the 1 carbon to form a new pi bond. This will push off the bromine, which will leave with its electron pair to form a bromide leaving group. This will form the product 1-methylcyclopentene and sodium bromide as byproduct. So, is this reaction following an E1 or E2 mechanism? Write out the rate law for this reaction. Draw a reaction coordinate diagram for this reaction.

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter25: Enolate & Enol Nucleophiles
Section: Chapter Questions
Problem 11CTQ
icon
Related questions
icon
Concept explainers
Question

1-bromo-1-methylcyclopentane is being reacted with sodium ethoxide in diethyl ether

Ethoxide will remove a proton from one of the carbons alpha to the carbon bonded to bromine. The electron pair from the carbon-hydrogen bond will move toward the 1 carbon to form a new pi bond. This will push off the bromine, which will leave with its electron pair to form a bromide leaving group. This will form the product 1-methylcyclopentene and sodium bromide as byproduct.

So, is this reaction following an E1 or E2 mechanism? Write out the rate law for this reaction. Draw a reaction coordinate diagram for this reaction.

Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 2 images

Blurred answer
Knowledge Booster
Ethers
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
Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:
9780618974122
Author:
Andrei Straumanis
Publisher:
Cengage Learning