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CHEM 2445 Lab Practical 1 Part A

1) The document describes an experiment to understand the SN1 substitution reaction mechanism between 2-chlorobutane, silver nitrate, and ethanol. It explores the stability of carbocation intermediates and possible carbocation rearrangements. 2) The procedure involves combining the reactants and heating them while monitoring the reaction. Techniques like TLC, FTIR, and NMR are used to analyze the products. 3) A data table ranks the reactivities of different organic chlorides in the SN1 reaction based on the stability of the carbocation intermediates formed, with tertiary carbocations being the most stable and most reactive.

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KAR
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725 views

CHEM 2445 Lab Practical 1 Part A

1) The document describes an experiment to understand the SN1 substitution reaction mechanism between 2-chlorobutane, silver nitrate, and ethanol. It explores the stability of carbocation intermediates and possible carbocation rearrangements. 2) The procedure involves combining the reactants and heating them while monitoring the reaction. Techniques like TLC, FTIR, and NMR are used to analyze the products. 3) A data table ranks the reactivities of different organic chlorides in the SN1 reaction based on the stability of the carbocation intermediates formed, with tertiary carbocations being the most stable and most reactive.

Uploaded by

KAR
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Karen Edmonds

Section Number: 403

Relative Reactivities of Organic Chlorides in SN1 Reaction

Objective

The goal of this experiment is to understand the SN1 mechanism between 2-chlorobutane, silver

nitrate and ethanol, and determine the relative reactivities of organic chlorides in a substitution

reaction. The reaction mechanism of SN1 and stereochemistry of the reaction products will be

explored.

Introduction

Chemical Equation and Mechanism of the SN1 reaction between 2-chlorobutane, silver

nitrate, ethanol:

Stability of carbocation intermediates:


The carbocation presented in the mechanism above is the most stable carbocation intermediate

that could be formed during this reaction. During SN1 reactions, the most stable carbocation

intermediate determines the product and the reactivity of the organic chlorides or other organic

compounds. Therefore, a tertiary carbocation, due to hyperconjugation, would be the most stable

intermediate whereas a primary carbocation would be the least stable intermediate.

Carbocation rearrangement:

Carbocation rearrangement can occur during an SN1 mechanism to produce a more stable

product. These rearrangements are known as hydride shifts, where a hydrogen moves from one

carbon to a less substituted carbon, and methyl shifts, where a methyl group will swap places

with the positive charge of the carbocation. Both rearrangements lead to a more substituted

positive charge, allowing the nucleophile to add to the carbocation in a more stable location.

Procedure

1. Combine 2-chlorobutane, silver nitrate and ethanol into a round-bottom flask and move

them to the bunsen burner.

2. Take a TLC plate to determine the Rf value of the starting materials.

3. Attach the condenser and nitrogen gas to the flask and heat the reaction mixture until the

desired product has been formed.

4. Perform a workup by adding the mixture to a separatory funnel and applying a workup

reagent.

5. Perform a distillation, if necessary, using the distillation apparatus until the desired

product has been obtained.

6. Take a TLC plate to determine the Rf value of the products.


7. Take an FTIR and H1NMR spectrum of the product using the FTIR and H1NMR

spectrometer in order to determine if the correct product was obtained.

Data Table

Organic Chloride Reactivity

5 (least reactive, slowest) - Primary


carbocations are the least stable intermediates
of an SN1 reaction.

2 - Benzylic carbocations are more stable than


ordinary carbocations because of their
resonance structures.

1 (most reactive, fastest) - This chloride will


form a tertiary carbocation which is the most
stable carbocation due to the donation of
electron density to the empty p orbital.

3 - Primary benzylic carbocations are not as


stable as secondary benzylic carbocations but
more stable than ordinary carbocations.

4 - Secondary carbocations are more stable


than primary carbocations.

Discussion and Conclusion

Discussion:
A substitution reaction occurs when a nucleophile replaces the leaving group of the substrate.

Substitution reactions can be SN1, where a carbocation intermediate is formed and the stability

of the carbocation determines the reaction rate, or SN2, where the reaction is concerted. During

an SN2 reaction, the reaction rate is dependent on the concentration of the substrate and

nucleophile. When determining which of the organic chlorides presented produces the fastest

reaction with silver nitrate & ethanol, we have to determine the reaction mechanism. The

mechanism is going to be SN1, a two step mechanism, therefore the reaction rate is determined

by the stability of the carbocation. The data table above provides explanations for how each

organic chloride was ranked for its reactivity.

Conclusion:

In this experiment, an organic chloride was the substrate whereas ethanol acted as the

nucleophile. The reaction underwent an SN1 mechanism, where a secondary carbocation was

formed. The chloride of the substrate was replaced with the ethanol, producing an ether.

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