All of the following are limitations to the Friedel - Crafts alkylation reaction except Highly deactivated aromatic rings are unreactive under Friedel - Crafts conditions. Friedel - Crafts reactions do not occur if an amine derivative is attached to the ring. Aniline derivatives are so reactive that over - alkylation is a possibility. Carbocation rearrangement can occur during the reaction.

All of the following are limitations to the Friedel - Crafts alkylation reaction except Highly deactivated aromatic rings are unreactive under Friedel - Crafts conditions. Friedel - Crafts reactions do not occur if an amine derivative is attached to the ring. Aniline derivatives are so reactive that over - alkylation is a possibility. Carbocation rearrangement can occur during the reaction.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter11: Ethers, Epoxides, And Sulfides

Section: Chapter Questions

Problem 11.18P

See similar textbooks

Similar questions

Enamines can serve as enolate surrogates in reactions at the a-carbon. In the reaction sequence, the structures of the enamine addition product – the initial iminium and its neutral tautomer – are shown. Draw the structures of the enamine and alkyl bromide reactants that would combine to form these intermediates, and draw the structure of the final product, obtained via hydrolysis of the neutral intermediate. iminium intermediate neutral intermediate tautomerization N. Reactants H20 hydrolysis product Draw the enamine and alkyl bromide reactants. Draw the hydrolysis product. ZI
Explain how and why rearrangements occurduring Friedel-Crafts alkylation reactions formingmore than 1 product. Also illustrate therearrangement reaction from the aboveexample.
You have learned two ways to make an alkyl benzene: Friedel–Craftsalkylation, and Friedel–Crafts acylation followed by reduction. Although some alkyl benzenes can be prepared by both methods, it is often true that only one method can be used to prepare a given alkyl benzene. Which method(s) can be used to prepare attached compound from benzene? Show the steps that would be used.
In the Friedel-Crafts alkylation of benzene, dialkylation is often a significant by-product. In the Friedel-Crafts acylation of benzene, diacylation is not a significant by-product. Why?
A common method where one alkyl halide is converted to another alkyl halide is known as Finkelstein reaction. In one example of this reaction the reaction of an alkyl chloride with potassium iodide is generally carry out in acetone to maximize the amount of alkyl iodine that this formed. Why does the solvent increase the amount of alkyl iodide. Hint: potassium idioide is soluble in acetone but potassium chloride is not.
Organometallic compounds act as nucleophiles under very specific conditions, and can generate alcohols, alkanes, among others. Describe in detail what these reaction conditions are so that organometallics can perform the addition reaction to carbonyl.
You have learned two ways to make an alkyl benzene: Friedel–Crafts alkylation, and Friedel–Crafts acylation followed by reduction. Although some alkyl benzenes can be prepared by both methods, it is often true that only one method can be used to prepare a given alkyl benzene. Which method(s) can be used to prepare each of the following compounds from benzene? Show the steps that would be used.
Explain why attempts to use esters for Friedel-Crafts acylation always lead to a complex mixture of alkylated and acylated products.
Provide a reasonable mechanism for the following transformation. Includeall intermediates as well as arrows showing the making and breaking of bonds
The aldol reaction is one of the most useful methods for the carbon–carbon bond formation. Over the years, chemists have gained many insights on the chemo-, regio-, diastereo-, and enantioselectivity of the aldol reaction and a lot of interest has been devoted to the development of economical and catalytic methods, such as transition metal catalysis, the decarboxylative aldol reaction, the reductive and alkylative aldol reaction, and the tandem isomerization/aldol reaction of allylic alcohols (Abiko, 2004). Two world famous chemists form Japan, Toshiro Harada and Atsushi Abiko, have made significant contributions to this field (Adachi, 2009; Adachi, 2008; Knochel, 2014). What contributions have Toshiro Harada and Atsushi Abiko made to the rapidly growing field of condensation reactions? List and cite two primary sources in APA format that demonstrate their discoveries.
Provide a step-by-step mechanism for the following reaction
The high reactivity of alkyl halides can be explained in terms of nature of C-X bond which is highly polarized covalent bond due to large difference in the electronegativities of carbon and halogen atom. This polarity is responsible for the nucleophilic substitution reactions of alkyl halides which mostly occur by Swa and Swa mechanisms. Sy reaction is a two-step process and in the first step, R-X ionizes to give carbocation (slow process). In the second step, the nucleophile attacks the carbocation from either side to form the product (fast process). In Swi reaction, there can be racemization and inversion. Swi reaction is favored by heavy (bulky) groups on the carbon atom attached to halogens. i.e., R,C-X>R;CH-X>R-CH,X>CH,X. In Sna reaction, the strong nucleophile OH attacks from the opposite side of the chlorine atom to give an intermediate (transition state) which breaks to yield the product (alcohol) and leaving (X) group. The alcohol has a configuration opposite to that of the…