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Give the SN1 mechanism for the formation of

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr ISBN: 9780321768414 33

Solution for problem 25P Chapter 6

Organic Chemistry | 8th Edition

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

Organic Chemistry | 8th Edition

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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 and is associated to the ISBN: 9780321768414. The full step-by-step solution to problem: 25P from chapter: 6 was answered by , 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 759 students have viewed the full step-by-step answer.

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