Describe the observed order of arene reactivity. What will be the order of the arene reactivity...

Describe the observed order of arene reactivity. What will be the order of the arene reactivity and how can i know?

Arene: Toluene, Acetanilide, Benzhydrol, Anisole, Diphenyl ether.

All five arenes were asked to be mixed with 35mL of acetic acid and 0.5mL of a 0.05M bromine solution.

what will be the fastest and slowest? what will be the order of reaction and why?

Expert Solution

Reactivity of arene means its ability to show electrophilic substitution reaction. The reactivity of arene depends on the stabilization of intermediate sigma complex. Let’s explain electrophilic substitution reaction in detail. (see Box 1 in image file)

The attack of pi-electron density at ortho position forms firstly pi-complex which then gives sigma-complex. The stability of sigma complex is governed by the stability of +ve charge generated. We can see that in both ortho and para attack case the +ve charge is on C which carries substituent R or we can say that on C which is ortho or para to E. If any group R is having electron donating ability will provide extra stability to the carbocation i.e. to sigma complex and will leads to the product formation. The final step of conversion is just regain of aromaticity which proceeds through loss of H from the carbon bearing E.
So its clear that any electron donating group either + Inductive or by + resonance effect will make the arene reactive towards electrophilic addition-elimination (i.e. overall substitution) reaction.
Hence among the given arenes we can make them into two groups as activating and deactivating groups.

Activators : Anisole ,toluene,
Deactivators: Benzhydrol, diphenyl ether and acetanilide.

Now according to +I, +R effect and –I, -R effect the decreasing trend of reactivity toward ESR is given as Anisole > Toluene > Benzhydrol > Diphenyl ether > Acetanilide.

The treatment of these arenes with Br2 in Acetic acid is an example of electrophilic substitution reaction or it’s a electrophilic bromination reaction. And hence the same trend as above will be followed here also.

queen_honey_blossom answered 2 years ago

reactivity order

1) arrange Pb, Mg, and Zn in order of their activities listing most active 2) arrange Cu, Ag, and Zn in order of their activities listing most active

Please explain the reactivity and orientation effects observed in each heterocycle. a. Pyridine is less reactive...

Please explain the reactivity and orientation effects observed in each heterocycle. a. Pyridine is less reactive than benzene in electrophilic aromatic substitutions and yields 3-substituted products. b. Pyrrole is more reactive than benzene in electrophilic aromatic substitutions and yields 2-substituted products.

rank (slowest to fastest) the following compounds in order of reactivity with respect to...

rank (slowest to fastest) the following compounds in order of reactivity with respect to an SN2 reaction. Explain your reasoning for the ranking you propose. The compounds are 1-bromo-3-methylbutane, 1-bromo-2,2-dimethylpropane and 2-bromo-2-methylbutane. Please provide clear explanations for your choices, thank you.

8. Predict the order of reactivity (and briefly justify your prediction): a) in cationic polymerization: styrene,...

8. Predict the order of reactivity (and briefly justify your prediction): a) in cationic polymerization: styrene, p-nitrostyrene, p-dimethylaminostyrene, p-methylstyrene b) in anionic polymerization: styrene, p-nitrostyrene, p-dimethylaminostyrene, p-methylstyrene

Rank in relative order the reactivity of primary, secondary, tertiary, allylic, benzylic and aromatic halides in...

Rank in relative order the reactivity of primary, secondary, tertiary, allylic, benzylic and aromatic halides in sodium/acetone test. Explain the reason for this difference in reactivity.

A. Arrange the organic halides below in order of decreasing experimental reactivity toward iodide ion (NaI...

A. Arrange the organic halides below in order of decreasing experimental reactivity toward iodide ion (NaI in acetone). B. Are there significant differences in the bromides and chlorides? C. What structural change correlates with reactivity in this mechanism (it should be SN2, right?)? Please explain answers! Thank you! halide reagents: 1-bromobutane, 2-bromobutane, 1-chlorobutane, 2-chlorobutane, benzyl chloride, 2-bromo-2-methylpropane, chlorobenzene, bromobenzene, 2-chloro-2-methylpropane

Ether reactivity? Contrast the reactivity of ehters with other organic compounds and discuss their importance as...

Ether reactivity? Contrast the reactivity of ehters with other organic compounds and discuss their importance as a solvent by citing two specific synthetic schemes that utilize ethers as a solvent (one example for ethyl ether and another one for crown ether).

Rank each of the following compounds in decreasing order of reactivity towards Friedel-Crafts alkylation. Most reactive...

Rank each of the following compounds in decreasing order of reactivity towards Friedel-Crafts alkylation. Most reactive = 1; if a compound will not react, rank it as "non" rather than assigning a numerical value. Compound A: fluorobenzene Compound B: phenol Compound C: benzaldehyde Compound D: acetophenone

What is the expected aromatic hydrocarbon reactivity of these compounds and why ? (which is the...

What is the expected aromatic hydrocarbon reactivity of these compounds and why ? (which is the fastest and which is the slowest and why?) a bromine solution in acetic acid was added to these compound. Toluene , Acetanilide , Benzhydrol, Anisole, Diphenyl ether

Arrange the alkyl bromides in order of reactivity in each reaction: 1-bromobutane, 2-bromobutane, cyclohexabromide, t-butylbromide

Question