Give the SN1 mechanism for the formation of

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L. G. Wade Jr

Problem 25P Chapter 6

Organic Chemistry | 8th Edition

  • 2901 Step-by-step solutions solved by professors and subject experts
  • Get 24/7 help from StudySoup virtual teaching assistants
Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L. G. Wade Jr

Organic Chemistry | 8th Edition

4 5 0 417 Reviews
18
0
Problem 25P

Give the SN1 mechanism for the formation of 2-ethoxy-3-methylbutane, the unrearrangedproduct in this reaction.

Step-by-Step Solution:

Solution 25P :

Step 1:

Here, we have to give the SN1 mechanism for the formation of 2-ethoxy-3-methylbutane

SN1 mechanism is a substitution reaction involving a nucleophile where 1 specie is involved in the slowest rate determining step. ‘SN’ stands for nucleophilic substitution and ‘1’ determines that the rate determining step is unimolecular. Rate determining step is a step in a multistep reaction, that controls the overall reaction rate.

Step 2:

SN1 mechanism for the formation of 2-ethoxy-3-methylbutane is as follows :

In SN1 mechanism, first, the dissociation of the halogen takes place. In the compound below, Br is the halogen and hence is a leaving group and dissociation of it takes place, producing secondary carbocation as shown below :

Here, the Bromide group, a halogen which is the leaving group, dissociates from the compound 2-ethoxy-3-methylbutane in presence of heat or light, and produces secondary carbocation. The carbocation is secondary carbocation, as the carbon atom bearing positive charge is bonded to 2 carbon atoms.  

The dissociation of halogen is the slowest step in the mechanism and in this step there is only 1 specie involved and a nucleophile is involved in the second step and hence it is called as SN1 mechanism.

Step 3 :

The above step describes the nucleophilic attack, which is a second step in the SN1 mechanism.

Here, the ethanol is supplied as nucleophile. A nucleophilic attack takes place from bottom, forming a bond with the carbocation and the substitution of nucleophile takes place producing the product that has OH group and has a positive charge on it.

Because the oxygen atom in the product has a positive charge on it, and there is still availability of ethanol to it, further reaction takes place where a hydrogen atom should be lost, to form a stable compound. This is the step 3 of  SN1 mechanism.

Step 3 of 3

Chapter 6, Problem 25P is Solved
Textbook: Organic Chemistry
Edition: 8
Author: L. G. Wade Jr
ISBN: 9780321768414

The answer to “Give the SN1 mechanism for the formation of 2-ethoxy-3-methylbutane, the unrearrangedproduct in this reaction.” is broken down into a number of easy to follow steps, and 14 words. Organic Chemistry was written by Sieva Kozinsky and is associated to the ISBN: 9780321768414. The full step-by-step solution to problem: 25P from chapter: 6 was answered by Sieva Kozinsky, our top Chemistry solution expert on 05/06/17, 06:41PM. This textbook survival guide was created for the textbook: Organic Chemistry, edition: 8. This full solution covers the following key subjects: unrearrangedproduct, mechanism, give, Formation, methylbutane. This expansive textbook survival guide covers 25 chapters, and 1336 solutions. Since the solution to 25P from 6 chapter was answered, more than 649 students have viewed the full step-by-step answer.

×
Log in to StudySoup
Get Full Access to Organic Chemistry - 8 Edition - Chapter 6 - Problem 25p

Forgot password? Reset password here

Join StudySoup for FREE
Get Full Access to Organic Chemistry - 8 Edition - Chapter 6 - Problem 25p
Join with Email
Already have an account? Login here
Reset your password

I don't want to reset my password

Need help? Contact support

Need an Account? Is not associated with an account
Sign up
We're here to help

Having trouble accessing your account? Let us help you, contact support at +1(510) 944-1054 or support@studysoup.com

Got it, thanks!
Password Reset Request Sent An email has been sent to the email address associated to your account. Follow the link in the email to reset your password. If you're having trouble finding our email please check your spam folder
Got it, thanks!
Already have an Account? Is already in use
Log in
Incorrect Password The password used to log in with this account is incorrect
Try Again

Forgot password? Reset it here