Why naphthalene is more reactive than benzene?

But in practise it is observed that naphthalene is more active towards electrophiles. This is because the delocalization in case of naphthalene is not as efficient as in benzene. Unlike in case of benzene all pi electrons of naphthalene are not equally delocalized on the 10 carbons.

Is benzene more reactive than naphthalene?

Naphthalene is more reactive than benzene, both in substitution and addition reactions, and these reactions tend to proceed in a manner that maintains one intact benzene ring.

Why is naphthalene less reactive than benzene?

Benzene has six pi electrons for its single aromatic ring. Naphthalene has two aromatic rings, but only 10 pi electrons (rather than the twelve electrons that it would prefer). This means that naphthalene has less aromatic stability than two isolated benzene rings would have.

Is benzene more stable than naphthalene?

Both are aromatic in nature both have delocalised electrons but naphthalene has more number of π bonds and hence more resonance structures and more delocalisation so overall it must be more stable.

Why naphthalene undergoes addition reaction more easily than benzene?

➢ Naphthalene undergoes oxidation or reduction more easily than benzene due to high resonance energy.

Stability order of Benzene Naphthalene Anthracene

Which position of naphthalene is more reactive and why?

Explanation: In the electrophilic substitution, position 1 in naphthalene is more reactive that the position 2 because the carbocation formed by the attack of electrophile at position 1 is more stable than position 2 because of the resonance since it has 4 contributing structures.

Which is more stable benzene naphthalene anthracene?

Thus benzene is most stable followed by naphthalene and anthracene.

Which is more aromatic benzene or naphthalene or anthracene?

There are three aromatic rings in Anthracene. Therefore the order of resonance energy as per the benzene ring in the decreasing order is : Benzene > Naphthalene > Phenanthrene > Anthracene.

Why naphthalene is aromatic?

As we are getting a whole number from, 4nπ+2 formula for naphthalene, so naphthalene is aromatic. Therefore, the naphthalene is an aromatic compound according to Huckel's rule because it has 4nπ+2 delocalised electrons. Note: Pi bonds are known as delocalized bonds. Pi bonds cause the resonance.

Is naphthalene electron donating?

Naphthalenes substituted with combinations of strongly electron-donating functional groups, such as alcohols and amines, and strongly electron-withdrawing groups, especially sulfonic acids, are intermediates in the preparation of many synthetic dyes.

Why does naphthalene undergo electrophilic substitution reaction at alpha position?

question. Electrophilic substitution reaction in naphthalene is quite similar to benzene reaction. The alpha position is more stabilized than the beta position. The carbocation formed at an alpha position after the attack of an electrophile is much more stabilized by its resonance than the second position.

Why the 1st position of naphthalene is more reactive than 2nd position explain giving mechanism?

Substitution usually occurs more readily at the 1 position than at the 2 position because the intermediate for 1-substitution is more stable than that for 2-substitution. The reason is that the most favorable resonance structures for either intermediate are those that have one fully aromatic ring.

What is the resonance energy of naphthalene?

The resonance energy for phenanthrene is 92 Kcal/mol, that for anthracene is 84 Kcal/mol and for naphthalene and benzene rings are 61 and 36 Kcal/mol respectively.

Is naphthalene more reactive than benzene towards electrophilic aromatic substitution reaction?

Naphthalene is more reactive towards electrophilic substitution reactions than benzene.

How many compounds are more reactive than benzene towards electrophilic aromatic substitution reaction naphthalene?

Among the given compounds, only five compounds are more reactive than benzene towards electrophilic aromatic substitution reaction.

Which is more reactive than benzene for electrophilic substitution?

Phenol is more reactive than benzene towards electrophilic substitution reaction. The donation of the oxygen's lone pair into the ring system increases the electron density around the ring. That makes the ring much more reactive than it is in benzene. The intermediate carbocation is more resonance stabilized.

Does naphthalene contain benzene?

naphthalene, the simplest of the fused or condensed ring hydrocarbon compounds composed of two benzene rings sharing two adjacent carbon atoms; chemical formula, C₁₀H₈.

Does naphthalene obey Huckel rule?

Naphthalene contain 10 π electrons. So, according to Hückel's Rule (n=2) naphthalene obeys (4n+2)π electron rule.

Is naphthalene aromatic or non aromatic?

Naphthalene, with two fused rings, is the simplest polycyclic aromatic molecule. Note that all the carbon atoms except those at the points of fusion have a bond to a hydrogen atom. Naphthalene, which has 10 π electrons, satisfies the Hückel rule for aromaticity.

What is the stabilization energy of naphthalene?

Naphthalene is a bicyclic aromatic hydrocarbon having a resonance stabilization energy per ring slightly less than that of benzene (36 kcal/mole).

Why is anthracene more reactive than benzene?

Anthracene has 25 kcal/mol less resonance energy than 3×benzene rings . Phenanthrene has 17 kcal/mol less resonance energy than 3×benzene rings .

Why is pyrrole more reactive than benzene?

And pyrrole, furan, and thiophene are all more reactive than benzene with EAS because the lone pair on the heteroatom can donate electron density into the ring by resonance, thus stabilizing the carbocation intermediate more effectively.

Which is the most prefer position for electrophilic substitution reaction in naphthalene?

Reaction Examples. Note: Naphthalene can undergo electrophilic aromatic substitution (EAS) reactions similar to benzene and generally prefers to substitute at the alpha position.

Why electrophilic substitution reaction occurs slowly in nitrobenzene than benzene?

Nitrobenzene, C₆H₅NO₂, undergoes the reaction millions of times more slowly. These observations are consistent with the role of the aromatic as a nucleophile in this reaction. Substituents that draw electron density away from the aromatic ring slow the reaction down.

What is Haworth process?

Haworth synthesis is a multistep preparation of phenanthrenes from naphthalenes by means of the Friedel–Crafts acylation with succinic anhydride, followed by a Clemmensen reduction or Wolff–Kishner reduction, cyclization, reduction, and dehydrogenation.