# Organic Chemistry## Substitution Reactions Exercise**Presented by Macmillan Learning**Consider the pair of reactions. Draw the organic products, then predict the type of substitution mechanism and compare the expected rates.### Reaction 1:- Organic reactant: **Chloroethane (\( \text{C}_4\text{H}_9\text{Cl} \))** - Nucleophile: **Fluoride ion (\( \text{F}^{-} \))** - Solvent: **DMSO (Dimethyl sulfoxide)**- Resulting product labeled as Product 1.### Reaction 2:- Organic reactant: **Chloroethane (\( \text{C}_4\text{H}_9\text{Cl} \))** - Nucleophile: **Fluoride ion (\( \text{F}^{-} \))** - Solvent: **H\(_2\)O (Water)**- Resulting product labeled as Product 2.### Instructions:**Draw Product 1:**- Use the interface options: Select, Draw, Rings, More, Erase.- Available elements: C (Carbon), H (Hydrogen), F (Fluorine).**Draw Product 2:**- Same drawing options and elements as above.### Questions:**Identify the mechanism of each reaction:**- [ ] Reaction 1 occurs by an \(S_N1\) mechanism.- [ ] Reaction 2 occurs by an \(S_N2\) mechanism.- [ ] Reaction 1 occurs by an \(S_N2\) mechanism.- [ ] Reaction 2 occurs by an \(S_N1\) mechanism.**Compare the rates of each reaction:**- ( ) Reaction 1 is faster than reaction 2.- ( ) Reaction 2 is faster than reaction 1.- ( ) Both reactions occur at the same rate.### Graphs or Diagrams Explanation:The interface is divided into two sections for drawing Product 1 and Product 2, offering tools for drawing structures with carbon, hydrogen, and fluorine. There are no graphs but visual elements to represent molecular structures.

In both reactions, no stable carbocation gets formed. Hence, both the reactions undergo by the SN2 nucleophilic substitution mechanism. The product of the reactions is shown as follows: Now, H2O is a polar protic solvent. It is capable to do hydrogen bonding with the F- nucleophile, also, due to the smaller size of F-, it gets trapped by the H2O molecules. On the other hand, DMSO is a polar aprotic solvent which cannot do hydrogen bonding. Thus, the rate of reaction in the H2O solvent is slower as compared to the rate of reaction in the DMSO solvent. So, reaction 1 is faster than reaction 2 Hence, the correct answer is:

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Consider the pair of reactions. Draw the organic products, then predict the type of substitution mechanism and compare the expected rates. Reaction 1: DMSO product 1 Reaction 2: H20 product 2 Draw product 1. Draw product 2. Select Draw Rings More Erase Select Draw Rings More Erase |7 | C H F H Identify the mechanism of each reaction. Compare the rates of each reaction. O Reaction 1 occurs by an SN! mechanism. Reaction 1 is faster than reaction 2. O Reaction 2 occurs by an SN2 mechanism. O Reaction 2 is faster than reaction 1. O Reaction 1 occurs by an S2 mechanism. Both reactions occur at the same rate. O Reaction 2 occurs by an SNI mechanism.

Consider the pair of reactions. Draw the organic products, then predict the type of substitution mechanism and compare the expected rates. Reaction 1: DMSO product 1 Reaction 2: H20 product 2 Draw product 1. Draw product 2. Select Draw Rings More Erase Select Draw Rings More Erase |7 | C H F H Identify the mechanism of each reaction. Compare the rates of each reaction. O Reaction 1 occurs by an SN! mechanism. Reaction 1 is faster than reaction 2. O Reaction 2 occurs by an SN2 mechanism. O Reaction 2 is faster than reaction 1. O Reaction 1 occurs by an S2 mechanism. Both reactions occur at the same rate. O Reaction 2 occurs by an SNI mechanism.

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...

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