Question: In comparing nucleophilic aromatic substitution reactions that differ only in the identity of the halogen that is the leaving group in the substrate, it is

In comparing nucleophilic aromatic substitution reactions that differ only in the identity of the halogen that is the leaving group in the substrate, it is found that the fluorinated substrate reacts faster than either of the cases where bromine or chlorine is the leaving group. Explain this behavior, which is contrary to the trend among the halogens as leaving groups in SN1 and SN2 reactions (in protic solvents).

Step by Step Solution

★★★★★

3.47 Rating (167 Votes )

There are 3 Steps involved in it

1 Expert Approved Answer

Step: 1 Unlock

In those cases where the S N Ar mechanism holds the fi... View full answer

Question Has Been Solved by an Expert!

Get step-by-step solutions from verified subject matter experts

Step: 2 Unlock

Step: 3 Unlock

Document Format (1 attachment)

877-C-O-S (955).docx

120 KBs Word File

Students Have Also Explored These Related Organic Chemistry Questions!

Nucleophilic aromatic substitution provides one of the common methods for making phenols. (Another method is discussed in Section 19-17.) Show how you would synthesize the following phenols, using...

We have considered nucleophilic aromatic substitution of pyridine at the 2-position and 3-position but not at the 4-position. Complete the three possible cases by showing the mechanism for the...

Section 17-12 showed how nucleophilic aromatic substitution can give aryl amines if there is a strong electron-withdrawing group ortho or para to the site of substitution. Consider the following...

a. (i) The reaction sequence shown in Figure 4 demonstrates the synthesis of a disubstituted benzene derivative N from compound L through an Electrophilic Aromatic Substitution reaction followed by a...

(i) The reaction sequence shown in Figure 4 demonstrates the synthesis of a disubstituted benzene derivative N from compound L through an Electrophilic Aromatic Substitution reaction followed by a...

Teach and explain : Chemistry of Aromatic Compounds Course Objectives: To expose students to the properties, preparation and reactions of benzene derivatives. At the end of the course students will...

just need question 3,4,5 6 teapects of the atrow ls allew the lormatien of the tartepeontint peoduch. 2. Draw the nactign mechansm fer the folsent wastion: \begin{tabular}{|l|l|} \hline Cononk...

please help me ASAP!!!! 1. Which substituted arene below is most reactive in Friedel Crafts chemistry? A. C. D. 2. Which substituted arene below is most reactive in electrophilic aromatic...

1. Aromatic compounds can react by electrophilic aromatic substitution (EaS). Provide the reagents on the arrow to allow the formation of the corresponding products. 2. Draw the reaction mechanism...

It is typically very difficult to do a substitution reaction on an aromatic ring when the leaving group is flanked by two other bulky substituents. Moreover, in Section 22.3, we found that...

Complete the code provided to add the appropriate amount tototalDeposit. #include using namespace std; int main() { enum AcceptedCoins {ADD_QUARTER, ADD_DIME,ADD_NICKEL, ADD_UNKNOWN}; AcceptedCoins...

A subdivision in Corvallis, Oregon, is shown in Figure P6.21. Rational method design is performed using the 10 - yr return period IDF curve of the Oregon Department of Transportation (1990) for Zone...

3. Consider the following data and corresponding weights. xi Weight (wi ) 3.2 6 2.0 3 2.5 2 5.0 8 a. Compute the weighted mean. b. Compute the sample mean of the four data values without weighting....

Developing a Release Plan needs the use of some predefined Release Prioritization Methods that are Industry and Organization specific and determined by the Organizations Senior Management. A) _TRUE_...

Using 1-butyne as the only source of carbon in the reactants, propose a synthesis for each of the following compounds. (a) CH3 CH2 CD2 CD3 (b) 1-butoxybutane (dibutyl ether) (c) octane

Outline a preparation of racemic desparlure, a pheromone of the gypsy moth, from acetylene and any other compounds containing not more than five carbon atoms. CH,(CH2) disparlure

2. An overview of a firm's cost of debt To calculate the after-tax cost of debt, multiply the before-tax cost of debt by (1T). Omni Consumer Products Company (OCP) can borrow funds at an interest...

Byron Books Inc. recently reported $18 million of net income. Its EBIT was $24.3 million, and its tax rate was 25%. What was its interest expense? (Hint: Write out the headings for an income...

Pappys Potato has come up with a new product, the Potato Pet (they are freeze-dried to last longer). Pappys paid $121,000 for a marketing survey to determine the viability of the product. It is felt...