Answered: Explain in detail the difference in the…

Explain in detail the difference in the rate of free radical bromination reactions of toluene and cyclohexane. Write neatly

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

Chapter9: Nucleophilic Substitution And Β-elimination

Section: Chapter Questions

Problem 9.15P

See similar textbooks

Related questions

Q: What product would be formed by the disrotatory cyclization of the given triene? Would this reaction…

A: Ring closure reactions are of 2 types - Disrotatory when 2 substituents more in opposite…

Q: Give mechanism and write a complete Energy Diagram for Sulfonation of Benzene:

A: When the benzene is treated with conc. sulphuric acid, benzene sulphonic acid is formed. This is…

Q: Rank these nucleophiles from most to least reactive for substitution reactions and give a brief…

A: The nucleophilicity of a species depends on various factors such as negative charge density,…

Q: Explain the reactivity of bromobenzene with sodium methoxide compared to the reactivity of…

A: The reactivity of bromobenzene with sodium methoxide compared to the reactivity of…

Q: Write the structures of all the alkenes that can be formed by dehydrohalogenation of the following…

Q: What is the expected rate law and mechanism for this square planar substitution reaction?

A: Given reaction:

Q: Select the compound(s) that will give only a single monochlorination product in its free radical…

Q: Write the mechanism for the reaction of 1-butanol with HBr and include a brief explanation of the…

A: Butanol reacts with HBr to give butylbromide via second order substitution mechanism. In this…

Q: Outline the synthesis of 1-bromo-2-methylpropane by using suitable alkene

Q: Predict the structure of the product formed when HCl adds to 1-Bromo cyclohexene. Also explain how…

A: Halogens are electronegative atom , thus it should have act as electron withdrawing group ,in…

Q: Give the product(s) that would be formed when 3-methyl-3-pentanol is subjected to acid-catalyzed…

A: Interpretation: We have to form dehydrated product for the molecule 3-methyl-3-pentanol .

Q: The Wittig reaction can be used for the synthesis of conjugated dienes as the example below,…

A: The Wittig reaction is a usefull method for converting of aldehyde and ketone with a triphenyl…

Q: With appropriate schematic diagrams, synthesize the alkane produced by treating cyclopentyl bromide…

A: Given

Q: Complete racemization had been observed in the product of a SN1 reaction of a haloalkane. How could…

A: In SN1 reaction, the product formed shows racemization. It means there is a presence of 50% of…

Q: name the two diene products that could be obtained in the double-dehydration reaction of…

A: Diene is the molecule with two double bonds. Dehydration is the reaction in which water molecule is…

Q: Name the two diene products that could be obtained in the double-dehydration reaction of…

A: Dehydration reaction proceed by the removal of water. The removal of a water from a compound will…

Q: What would be the product ratio in the chlorination of propane if all the hydrogens were abstracted…

A: The reaction of chlorination of propane is shown as follows: Here chlorinated product is formed as…

Q: Be sure to answer all parts. Complete the reactions to show the synthesis of the following compound…

Q: Write a reasonable mechanism for the formation of cyclohexylbenzene from the reaction of benzene,…

A: Write a reasonable mechanism for the formation of cyclohexylbenzene from the reaction of benzene,…

Q: Describe the structure of the methylethium tetramer (including the orbitals involved in the bonds)…

A: Methyl lithium tetramer Li4 (CH3)4is an organometallic compound. This tetramer is an example of…

Q: Although derivatization of a reaction should be avoided as much as possible according to the…

Q: Explain why the ratio of reactants of Nitration of Bromobenzene and reactants of friedel-crafts…

A: Nitration is the reaction of introducing a nitro group into the ring. This is an example of…

Q: Free-radical chlorination of hexane gives very poor yields of 1-chlorohexane, while cyclohexane can…

A: Halogenation is a chemical reaction in which the halogen (for example, chlorine) is added into an…

Q: Alkenyl halides such as vinyl bromide, CH2=CHBr, undergo neither SN1 nor SN2 reactions. What factors…

A: SN1 reaction is a nucleophilic substitution reaction. It is a uni-molecular reaction which takes…

Q: Provide answer to the attached

A: Applying concept of SN2 mechanism.

Q: [a] Provide a rationale for the fact that 3-bromobut-1-ene is the kinetically controlled product the…

Q: Explain the difference in the rate of free radical bromination reactions of toluene and cyclohexane.

Q: Write the overall balanced equation and mechanism for the transformation of bromobenzene into…

A: Organic reactions are those in which organic reactant react to form organic products. Grignard…

Q: Label the reactive features of the following reactants, select the most reactive feature, then write…

A: In the reaction of bromine water Br and OH add on the double bond via anti addition. In this…

Q: Write the sequence of steps required for the conversion of benzene into benzenediazonium chloride.

A: Benzene diazoniumchloride can be prepared by benzene. The process involve the formation of…

Q: Briefly explain in words about radical involvement in Grignard reagent formation for synthesis of…

A: the starting reactants for the synthesis of triphenylmethanol are phenyl magnesium bromide and the…

Q: Chlorobenzene is extremely less reactive towards a nucleophilic substitution reaction. Give two…

A: There are some electron displacement effects like , resonance effect, inductive effect etc. decides…

Q: To illustrate rearrangement in the Friedel-Crafts alkylation reaction draw the structure of the two…

Q: How many monobromination products would be obtained from radical bromination of methylcyclohexane?

A: Here, we have to find the number of monobromination products that will be obtained from the radical…

Q: Ignoring isotope effects, after one E2 elimination with ethoxide, which bromine will predominate in…

A: As the E2 elimination reaction follows is anti periplanar mechanism i.e it takes place only when the…

Q: What is the most stable radical that could form from 2,2-dimethylbutane and the structure of the…

Q: In the Janovsky reaction, explain why the meta-dinitrobenzene acts as an electrophile. What is the…

A: In Janovsky reaction, aldehydes and ketones with α-methylene groups react with m-dinitrobenzene in…

Q: Explain why the rate of the reaction of 1-bromo-2-butene with ethanol is increased if silver nitrate…

A: The SN1 reaction occurs when alkyl halide dissociates to form a carbocation, which will then react…

Q: Write the free radical monosubstituition mechanism for the bromination of cyclohexane to give…

Q: In the dehydrohalogenation of bromocyclodecane, the major product is cis -cyclodecene rather than…

A: In the dehydrohalogenation of bromocyclodecane, cis-cyclodecene and trans-cyclodecene are formed.

Q: Differentiate between stereoselective and stereospecific reaction and apply this knowledge on…

A: Stereospecific reaction : A reaction in which only one stereoisomer is allow to be formed.…

Q: Provide a reasonable synthetic strategy for the synthesis of a racemic mixture of (1R,2R) and…

A: Reactant Methylcyclopentane Product a racemic mixture of (1R,2R) and…

Q: the reaction mechanism for the production of hexachlorophene starting from 2,4,5 trichlorophenol…

A: Protonation of formaldehyde in the presence of concentrated sulfuric acid is shown below.

Concept explainers

Aromatic Compounds

Aromatic organic compound or aromatic system is an important class of hydrocarbons under the branch of organic chemistry. Aromatic compounds are also called arenas. The definition of aromatic organic compounds can be stated as a class of organic compounds with a planar cyclic ring of atoms bonded through alternated single and double bonds. Due to these alternating bonds, a peculiar feature termed as ‘resonance’, that is, delocalization of pi electrons or the electrons is shared within the atoms of the ring which are present in the aromatic compounds. The word ‘aromatic’ includes a Greek word ‘aroma’ which means smell, indicating that they were named as such due to the sweet odor they produce. Many well-known flavors such as vanilla, cinnamon, and few scents from flowers are extracted from aromatic compounds. Benzene with chemical formula C6H6 is a very common aromatic compound that contains six atoms of carbon held in the cyclic ring of alternate double bonds. It is also to be noted that not all aromatic compounds contain benzene ring. This can be explained by Huckel’s rule.

Question

Explain in detail the difference in the rate of free radical bromination reactions of toluene and cyclohexane. Write neatly

Expert Solution

This question has been solved!

Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.

This is a popular solution!

SEE SOLUTION Check out a sample Q&A here

Step 1

VIEW

Step 2

VIEW

Trending now

This is a popular solution!

Step by step

Solved in 2 steps with 1 images

SEE SOLUTION Check out a sample Q&A here

Knowledge Booster

Learn more about

Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.

Similar questions

Explain with the help of electronic effects, ‘generally haloalkenes undergo nucleophilic substitution reactions whereas haloarenes undergo electrophilic substitution reactions’.
Explain how Hammond's postulate accounts for the higher selectivity of bromination reactions as compared to chlorination reactions.
The Friedel-Crafts Alkylation of p-xylene n-propyl bromide can result in an isopropyl as well as n-propyl substitution. A) Write the chemical equation involved in this reaction. B) Which will be the major and minor product? What do you expect will be the ratio of n-propyl to isopropyl substitution for p-xylene?
Substitutions on aromatic rings are generally carried out by electrophilic substitution, but for the synthesis of phenolic compounds and alkoxy benzene it is carried out by nucleophilic substitution, explain why this is so .
Explain with the help of electronic effects, ‘generally haloalkenes undergo nucleophilic substitution reactions whereas haloarenes undergo electrophilic substitution reaction
Explain the difference in the rate of free radical bromination reactions of toluene and cyclohexane.
The relative rates of reaction of ethane, toluene, and ethylbenzene with bromine atoms have been measured. The most reactive hydrocarbon undergoes hydrogen atom abstraction a million times faster than does the least reactive one. Arrange these hydrocarbons order of decreasing reactivity.
When bromomethane undergoes solvolysis in a solvent mixture composed of 90% water/10% acetone, the reaction rate is faster than when the same compound is solvolyzed in 80% water/20% acetone. Explain.
why do (R)-3-chloro-1-methylcycloprop-1-ene and 5-Bromo-1,3-Cyclohexadiene react differently with cyanide (why doesn't cyanide pass through its usual mechanism for these two products and what did you obtain these specific products)
Which halogenoalkane can undergo faster hydrolysis in the presence of NaOH , an iodoalkane or a chloroalkane and why?
Write the structures of all the alkenes that can be formed by dehydrohalogenation of the following alkyl halides using sodium ethoxide. Assuming that Zaitsev's rule applies, predict the alkene formed in greatest amount in each case.
Free-radical chlorination of hexane gives very poor yields of 1-chlorohexane, while cyclohexane can be converted to chlorocyclohexane in good yield. How do you account for this difference?